Genre: Hip Hop

Label: Roc-A-Fella Records / Def Jam Recordings

Release Date: September 11, 2001

Vibe: 🎤🔥

👉 Click the GIF to stream the album on your favorite platform:

I think hip-hop is, just now, starting to realize the bottomless potential of nostalgia acts. Rock, pop, and, to a degree, R&B figured out a long time ago how much money there was to be made if you tapped into this market, and that acumen has helped various artists enjoy lucrative second, third, and even fourth acts in their ever-elongating careers. Consider this: The top-grossing touring artists of 2025 were Beyoncé, Oasis, and Coldplay. In 2024, names like P!nk and Bruce Springsteen cracked the Top 5. And yet, despite all the evidence that extracting every last dollar out of the general assumption that “music was better back then,” hip-hop has largely ignored this strategy. For a long time, commercially successful rappers could bank on raking it in for 10, maybe 15 years if you were lucky. After that, you’d be market-corrected by the latest, hottest model that labels and tastemakers would replace you with on the assembly line. A dog-eat-dog existence, which kind of feeds into the paranoid ethos of rap overall, if you ask me, but it has been the reality.

Now, that tide is turning. Names you’d file into the ecosystem’s elder category, such as Snoop Dogg (54), Missy Elliott (55), LL Cool J (58), and Slick Rick (61), have all embarked on successful tours and, quietly, released good-to-great new records in the past decade. But the biggest sign, for me, that hip-hop is moving into uncharted territory with brand-name “legacy acts” was Jay-Z’s string of shows at Yankee Stadium in July 2026. The first show focused its tribute on Reasonable Doubt, which celebrated its 30th anniversary earlier that summer, drawing rave reviews and fanboy euphoria in equal measure. The second shifted the spotlight to The Blueprint, a rap-pop blockbuster that turns 25 years old this week, and Jay gave fans their money’s worth. Pharrell was there. So was Eminem. It felt bigger and more grandiose than anything the Brooklyn native had done to that point in his career, which is saying a lot. It’s a textbook example of pop culture mythmaking, but it hardly matters. So is every Beatles Super Deluxe box set. Even with the eye-watering price of admission, people will gladly pay.

In a way, those re-assertions of his greatness are a throwback to where Jay was in his career while making The Blueprint. To say he “needed” a hit or a return to form would be overdramatic, but he definitely needed to record and release a record like this. His previous three albums—Vol. 2… Hard Knock Life, Vol. 3… Life and Times of S. Carter, and *The Dynasty: Roc La Familia—*traded in the discipline and precision of his debut record for volume. Each new record came more bloated and cameo-heavy than the rest. They still sold well (north of 10 million units combined in the US) and scored him several Top 20 singles, but he was letting his brand pull him in too many different directions. At the time, he was also awaiting two separate criminal trials, for gun possession and assaulting record exec Lance “Un” Rivera at a Manhattan nightclub. The ground under the empire he was building was beginning to quake.

Oh, and let’s not forget the Prodigy and Nas beefs, which are essential B plots in this whole narrative. The former took issue with Jay-Z after hearing “Money, Cash, Hoes,” which features lyrics that the late Mobb Deep veteran thought spoke out of school regarding the East Coast-West Coast feud. The Nas beef had been simmering on the stovetop since 1996, when he supposedly failed to show up for a Reasonable Doubt recording session. Eventually, Nas and Roc-a-Fella crew member Memphis Bleek got into it, trading petty bars, a back-and-forth that crested with “Stillmatic,” where Jay is explicitly mentioned. The rebuttal, an early version of “Takeover” performed at Hot 97’s Summer Jam 2001, is still considered a seismic event in hip-hop history. Among other things, he made it clear that Nas was a has-been, a once-mighty emcee that he was more than willing to take (or retake) the East Coast crown from. The Blueprint, with all its fiery hubris, makes the case that, for a while anyway, he succeeded.

Every single bar Jay spits on this tracklist shapes that persona for every conceivable angle. The economy of the writing and the dexterity of his wordplay are all the more impressive because of how compressed the production schedule was. He wrote the bulk of the songs on The Blueprint in just a couple of days. The entire recording process only took two weeks. From a performance perspective, he was operating at a level of finesse and widespread appeal that no one else was reaching in 2001. The proof is in a stretch in the album’s back half, from the relentless “U Don’t Know” to the benediction that closes the supple windows-down cruiser “All I Need.” In that group, you have the Latin-infused Timbaland groove “Hola Hovito,” the coming-of-age braggadocio of “Never Change,” and the even more soulful swagger of “Heart of the City,” my pick for the best track on this LP. Roughly 15 minutes long, it’s a near-unassailable academic case for the best writing and sequencing stretch on any album in hip-hop history.

All that said, Jay has a worthy co-star on The Blueprint: the production. It was one of the first harbingers of the “chipmunk soul” movement, with slick, smooth, often maximalist beats built around instantly recognizable, pitched-up R&B and pop samples. The best-known example is the Jackson 5 inclusion on “Izzo (H.O.V.A.),” a beat that both Cam’Ron and Ghostface Killah passed on before it made its way to Jay-Z. Some “real” hip-hop heads decried its use of such a top-drawer sample as the primary backdrop for such gritty storytelling, but it’s a (um) blueprint that’s been used and reused by countless rappers since, including the man who produced it, Kanye West. He and Just Blaze, both relatively anonymous outside the confines of the Roc-a-Fella extended universe, each handle four instrumentals like they’re presenting these opulent pearls to a royal sultan, polished and shined to within an inch of their life. Whether it’s the lush fragrance of “Girls, Girls, Girls” or the unruly scream and stomp of the Doors sample on “Takeover,” the production is never anything less than the cinematic stage its protagonist needs.

The Blueprint dropped on September 11, 2001, only a few hours before the day took on an entirely different meaning for Jay’s sizable global audience. It still did numbers, opening atop the Billboard 200 and selling nearly a half-million copies in its first week of availability. It was certified 2x Platinum within eight months and, as of this writing, has moved well over 3 million units. Critics agreed it was one of the year’s best releases, making it a mainstay on various year-end lists. And, more importantly, rap music crafted with commercial aspirations continues to live in its long, ever-widening shadow. The unmistakable sampling strategy that some corners of the genre dismissed as an artistic shortcut rather than an achievement is now standard operating procedure. The majority of hits churned out by Drake, Kendrick Lamar, DJ Khaled, and many others owe at least a small debt to The Blueprint and how it balanced both sides of that equation to perfection.

What’s funny is that, a little over a year after this smash, Jay-Z released The Blueprint 2: The Gift and the Curse, and it’s like he didn’t learn anything from this experience. He was back to his pre-Blueprint ways, preoccupied with overstuffing every inch of real estate on the record with guest verses and competing ideas. Compared to this razor-sharp outing, it’s an incoherent mess that makes you stop and wonder if he got too bored to care about the output for a few years. He’s dropped plenty of quality material since, including The Black Album and 4:14, but the inconsistencies didn’t line up with the Jay that materialized in 2001. Fire in his belly, score-settling on his mind. It’s the autobiography he prefers to be known by, a poor kid who got out first by selling drugs, then by making hit records about the spoils that come with the lifestyle. To his credit, that story doesn’t devolve into an after-school cautionary tale or a tedious, street-level screed. There’s no guilt or remorse to be found. He is who he is, and here, when he’s at the top of his game, he owns prime real estate on rap’s Mount Rushmore.

Which Jay-Z song, from this album or another, hits the hardest? Sound off in the comments.

Genre: Pop, R&B, Electrofunk

Label: Jive Records

Release Date: September 8, 2006

Vibe: 🕺✨

👉 Click the GIF to stream the album on your favorite platform:

Picture this: It’s my prom night, senior year of high school, and the DJ drops “SexyBack” into a set built around the big movers and shakers of Top 40 radio from the summer of 2008. I’m talking Rihanna, Kanye West (back when that was still his name), Katy Perry, Chris Brown (ugh), Lil Wayne, and Metro Station (IYKYK). A mixed bag but one I have mostly fond memories of. Even though “SexyBack” had been out for nearly two years, none of us could get enough of that beat. A bunch of sweaty teenagers, dressed to the nines, swept up in this inescapably jubilent energy, our limbs bending and stuttering to that funky, electro-adjacent groove. It wasn’t quite EDM (that crossover explosion was a few months away), it wasn’t quite the clean-cut R&B of Timberlake’s previous record, Justified, and it wasn’t as hip-hop-forward as maybe it thought it was. Instead, it felt like this completely new thing, and that thing was such a sonic turn-on for my brain.

I have a soft spot for Justin Timberlake’s discography, partly because he’s been in my life since the very beginning of my music nerddom. I was the exact right age for NSYNC’s turn-of-the-century pop radio coup, where every kid on my street could bust out the dance moves from the “Bye Bye Bye” at a moment’s notice. I was in my brooding, “angry young man” phase when “Like I Love You,” “Rock Your Body,” and “Senorita” were popping off. In my twenties, I got way too dressed up and went on dates with women I was way too intimidated by to see several of his big-screen star vehicles like Friends With Benefits (which has its moments), In Time (which I recall being loud and dumb), and Runner Runner (louder and dumber). Then, a couple of years before Covid, my now-wife and I saw Timberlake in concert on his tour supporting Man of the Woods. It was a lot of fun! They even sat around a fake campfire at one point and sang a Jackson 5 song. Adorable.

Of all those pop culture artifacts, FutureSex/LoveSounds is probably his musical apex. The pop&B smash hit dominated the charts and airwaves for the better part of 2 years and sold roughly 10 million copies worldwide (4 million of those in the United States alone). Those numbers eventually got the record ranked among Billboard’s greatest albums of all time and added to the Rock and Roll Hall of Fame’s archive. It’s also kind of nuts how many producers and songwriters working in pop, R&B, hip-hop, EDM, and a host of other genres still crib from parts of this tracklist. The cold-fusion electrofunk largely architected by Timothy “Timbaland” Mosley and Nate “Danja” Hills blazed a trail for so many spinoffs and imitators that it’s difficult to estimate how many more millions in sales they should indirectly get some credit for, but that number isn’t small. In total, six singles from FutureSex/LoveSounds made it onto the Hot 100, staying power that, when I was entering prom season anyway, wasn’t common at all.

This album came after a three-year hiatus for Timberlake, which is odd considering how successful Justified was in 2002-03. Despite his clear signal that he wanted to pull away from the boy band image that had initially made him famous, it was all most people wanted to talk to him about. Clearly, he wasn’t interested in a reunion or, zooming out, returning to that same musical well again. If we’ve learned nothing from JT’s career, it’s that he refuses to stay in a single lane long enough to be pigeonholed there (double-edged sword and all that, but still true). So, instead, he decamped to Timbaland’s then-newly built Thomas Crown Studios in Virginia Beach, where Danja later joined them. According to multiple sources, no one really walked in there with a plan. There wasn’t a ton of material pre-written for the sessions, nor did any member of that main trio have an inkling of what the vibe would be, except that they wanted it to be different.

Consider the creative process that yielded “What Goes Around…Comes Around,” a sweeping cinematic pop kiss-off that netted Timberlake two Grammy nominations (he won for Best Male Pop Vocal Performance but lost to Amy Winehouse’s “Rehab” for Record of the Year). As Danja recounted to MTV, this massive-sounding song came out of being open to happy accidents. “I think that was the beauty of the whole project,” he said. “Nobody had a thought about anything. None of us was aiming for anything.” Out of nowhere, he played a guitar riff that caught JT’s ear, which got the singer humming the eponymous hook. Everything started fitting together quickly, and, within an hour, Timberlake was in the booth, recording his vocals, all without any lyrics written down on paper. I believe the common parlance for that phenomenon is “locked in.”

Ultimately, it’s a concoction that Danja likened to scoring a film, albeit with the signature Timbaland Southern thump underpinning the quivering strings and falsetto. The arrangement ebbs and flows effortlessly with Timberlake’s performance, never threatening to overtake his starring role, but also refusing to reduce itself to background schmaltz. “Justin’s telling a story, and where the story gets interesting, that’s where the music has to change and take you to the next scene,” Danja explained. “It just takes you to the end, dies out, breaks down, and then it gets even more dramatic with the interlude. The song is like you’re crying, and you’re feeling all the heartbreak. But the interlude, that’s anger, and it’s vengeful.” The full listening experience (not just the single version) has aged like a fine wine against the backdrop of Timberlake’s maturation as a pop music mainstay. I’m trying to think of a track that tops it in his discography, but nothing’s coming to mind. A hedge, but it’s out of love.

The entire album came together in similar fashion. In an interview with Zane Lowe, Timberlake explained that the earworm of a hook that opens “SexyBack” was a real-time riff over Timbaland’s beat. Rinse and repeat with “My Love,” “Sexy Ladies,” “Until the End of Time,” and several others. “Every day brought out a different feeling,” the producer later said of the recording process. JT and the rest of his team were listening to a lot more rock and old-school R&B (specifically, David Bowie and Prince) while making this record, and you can hear it in nearly every note. There’s an edge to his polished delivery that, back in 2006, I hadn’t heard from him before. That sweet, supple charisma was seasoned with a pinch of paranoia and desperation in certain moments, which I found fascinating. Underneath all the horny posturing, you get the sense that there’s a side of him who would’ve left a Favreau answering machine message or two if given the chance.

As I’m sure some albums do for you, FutureSex/LoveSounds instantly transports me back to the end of my high school years, a period of my life that I look back on with bittersweet affection. I didn’t enjoy actually being in or going to high school (for the most part, I couldn’t wait to leave), but, with the benefit of hindsight, I see how hard I was on myself and, sadly, how unwilling I was to let myself relax and live in the moment, despite ample opportunity to do so. On the occasions that I did, mostly in the last two years before I graduated, this album was a big part of the soundtrack. “Summer Love” was the track that spilled out of rolled-down car windows during aimless drives and parking lot seances, where my friends and I talked breathlessly about nothing at all. Part of me wishes I’d done more of that, whatever “that” was, but another part of me wouldn’t change a thing. That’s the beauty of growing up. You take everything, warts and all, and end up cracking a smile remembering it in crystal-clear flashes.

Anyone else a Justin Timberlake fan? Shout out any favorite tracks of his in the comments.

The Who may be to the British Invasion and the classic rock canon what Star Wars is to cinema: endlessly influential, but so much so that the art itself often gets obscured by that outsized reputation.

To compare apples to apples temporally, The Beatles get a lot of credit (mostly rightfully) for changing the face of rock and pop music during their heyday, but, somehow, I don’t think the Who get enough of the same shine. In addition to amassing a huge following on the strength of their live shows, they’ve been credited with originating the rock opera, power chords, instrument-smashing as a rite of passage, and windmill strumming theatrics.

And they did it all with one of music’s most volatile creative nuclei. You’d think that Pete Townshend’s angst-riddled songwriting and massive architectural ambitions would be in direct conflict with Roger Daltrey’s bruising brand of singing. Bassist John Entwistle was the epitome of melodic precision and control on the bass, while Keith Moon was anything but restrained on drums. One of my big takeaways as I went through their studio discography was that, on paper, nothing about those combinations should work, but on record, they’re frequently dazzling together.

I won’t spend a ton more time waxing poetic about the Who’s history or accomplishments. Instead, I’ll leave that to pros like , who literally wrote a damn book about one of their most popular projects. The last detail I’ll mention is that I have clear memories of doing the air-drum cymbal work along to the chorus in “Who Are You” every time the CSI opening credits flashed across the screen back in the day. That, and laughing my head off every time one of Caruso’s one-liners was punctuated by Daltrey’s screech from “Won’t Get Fooled Again.”

If you’re new here, the rules for my discography rankings are simple. I rank every official studio album from worst to best (reminder: “worst” doesn’t mean “horrible”), in ascending order of quality. No greatest hits, live albums, or bootlegs need apply, unless they’re absolutely indispensable to the artist’s career narrative (e.g., I would never discuss Peter Frampton’s discography without delving into Frampton Comes Alive).

Specific to the Who, Odds and Sods is a borderline case. As its namesake suggests, it’s a collection of studio outtakes that Entwistle put together and released to combat the rampant unofficial tapes people were selling of their concerts. I went back and forth on whether or not to include it and, because I’m a completist at heart, I’ve included it in my rankings, despite it being a quasi-compilation thrown together to have something to put out there.

That’s it. Enough babbling. Let’s get into it.

We begin:

13. A Quick One (1966)

Let’s make this a quick one for 1966’s A Quick One.

This record is, in a word, uneven. That’s not a symptom unique to this Who album, but it’s the moment in their discography where it was the greatest distraction. Like many of their British Invasion brethren, this was a sophomore record that was somewhat rushed to market to capitalize as much on the group’s burgeoning popularity on the back of singles like “I Can’t Explain” and “My Generation.” But, crucially, most of the pop and R&B sensibilities that made those and other early Who tracks accessible are scrubbed out of the arrangements here.

That difference is due in part to the new deal their then-manager Chris Stamp had signed with New Action Publishing. As part of the agreement, each band member received a £500 advance provided they wrote two songs for the new record. That incentive led the band to rely the least on Townshend songwriting as they would at any point in their history, with the guitarist’s popular singles “Happy Jack” and “I’m a Boy” excluded from the tracklist as a result. The songs that did make it are psychedelic, bombastic, and, at 51 minutes, an endurance test.

The centerpiece, a nine-minute mini-opera “A Quick One, While He’s Away,” is the reason to listen. It’s the first tangible proof that Townshend was already looking to the future when it came to song structure, how multiple vignettes might blend into a stronger, more affecting suite of music. The rest of the album falls somewhere between forgettable and grating, including such shameless exercises in novelty as a cover of the Batman theme. Just, why?

12. Endless Wire (2006)

Endless Wire ended a 24-year break between studio releases for the Who, one that came on the heels of extreme tumult in the band’s history. Entwistle died of a heart attack the night before the first stop of a scheduled US tour in 2002, an event that didn’t stop Townshend and Daltrey from pressing forward with the rest of the dates. Controversial, to say the least. Then, in 2003, Townshend was arrested in conjunction with Operation Ore, a UK-wide crackdown on internet child porn. He later admitted to using his credit card to access images of child abuse, though he claimed it was part of research into the British banks’ connection with the trade. No criminal charges were laid against Townshend in the end, but he did have to register as a sex offender.

So, a lot of unsettling, potentially career-ending baggage. But according to interviews Townshend and Daltrey gave mid-decade, those struggles brought them closer together as creative partners, resulting in a year-and-a-half recording process to bring this 28-track monster to fruition. There’s a lot of legacy-affirming going on, both as subtext and, like on opening track “Fragments,” which lifts its main synth riff directly from a 35-year-old Who classic, text. For some fans, that will be enough. The few flashes of brilliance, like on “Mike Post Theme,” where the surviving duo turn back the clock with surprising ferocity, may also be enough to merit a recommendation. For me, it didn’t quite get there.

It’s due in part to a sequencing issue. There’s a lot of starting and stopping on this album, which undercuts a lot of the momentum and excitement they show they can build in two- or three-track sprints, but are unfortunately unable to sustain for much longer. The acoustic, more folk-leaning balladry sounds at odds with the heavier, livelier material on the tracklist, a dynamic that prevents everything from holding together as well as maybe it should. The second side, devoted entirely to a mini-rock opera, “Wire & Glass,” also doesn’t land with the urgency and potency of the band’s most respected work.

Does all this mean Endless Wire is bad? Not necessarily. Maybe “distracted” is a better word. For nearly an hour, the Who sound more interested in reminding you of what they were than in showing you what they still could be.

11. Who Are You (1978)

Out of all the rankings on this list, Who Are You slotting in this low pains me the most. Why? Because I adore the title track. The funky bass and synth work, the effects-drenched guitar crunch, the crisp-yet-manic maneuvering on the hi-hat and toms. Oh, and Daltrey’s full-throated performance on lead vocals. All exceptional, all coming together for one of the catchiest songs the Who’s original lineup ever made. It was also the last studio album completed before Moon’s death. He overdosed on a powerful sedative prescribed to combat his alcoholism only a few weeks after the LP’s release. He was 32.

It’s one of the most bittersweet “what if” moments in the classic rock canon. Had Moon been able to get and stay sober, continued to make records, continued to play as only he could, what would the 1980s have looked like and sounded like for the band? It’s difficult to say, but throughout this tracklist, you can sense the shift they were trying to make. The production style moved toward cleaner, more controlled lines, while still leaving room for their trademark brute-force energy. Theoretically, it makes sense, and plenty of bands went down that road in the post-disco era, but, on this record, it feels limiting, like insisting someone keep a powerful sports car in first gear.

Beyond the title track, the rest of Who Are You is mixed. “Had Enough” and “Trick of the Light” are the next-best offerings, though even those two tracks are sabotaged by this inexplicable thinness in the mixing, which takes a lot of their individual bite away. For a group that had been so obsessive, to that point anyway, on studio craft and prided itself on how well-calibrated those instrumental elements were, it’s a perplexing final result. Even the most recent 2022 digital remaster didn’t totally fix that issue. In a way, it’s a good example of what made the Who so frustrating at times. At their most awe-inspiring, you could make the case for them as the world’s greatest rock band. Sadly, the more they recorded, the harder it was to keep that switch turned on.

10. My Generation (1965)

Let’s put My Generation, the Who’s proper full-length debut, into perspective.

The underappreciated aspect of this album is that the Who hadn’t been the Who for very long prior to its release. Keith Moon auditioned for them in April 1964, when they were still calling themselves the High Numbers, replacing Doug Sandom as the band’s rhythmic anchor. In November, the group recorded “I Can’t Explain,” which, when it dropped a month later as a Decca single, popped off in the UK, peaking inside the Top 10. As that song was having its moment in the sun, the Who started work on this first LP, ripping through mostly R&B covers before shifting to original material in a second recording session in October 1965.

The end result, released in December 1965, is decent, occasionally brilliant, and, in a revelation that will probably not surprise you, an enormous mess. That’s not a condemnation, by the way, but an unavoidable symptom of a mercurial rock band trying and semi-succeeding at finding their identity. I don’t think you get the whole Who experience on this record, or at least not the one you’d associate with their best-known rock radio staples. The debt to Motown, late-50s and early-60s R&B, and even a little blues, as demonstrated by Daltrey’s abrasive cover of Muddy Waters’ “I’m a Man.” The Rolling Stones were “guilty” of the same cover-heavy mindset at around the same point in their trajectory, so let’s call it a residue of the era.

What’s worth the price of admission are the well-known singles, “The Kids Are Alright” and the raucous title track. The former is a fascinating early example of a more sophisticated, pop-leaning sound from the Who that they’d dip back into only when they really felt it necessary, which is a double-edged sword of sorts because Townshend is such a masterful pop craftsman. There’s a world in which they pump out increasingly pop-forward fare and reap the rewards of a legacy that might hue closer to the Beatles’ overall. That said, do we want to live in a world where unhinged proto-punk and quasi-metal gems like “My Generation” don’t exist? From Entwistle’s lights-out bass playing to the feedback-drenched chaos that builds towards the end of the song, I don’t think there’s a scenario where I’ll ever tire of it.

9. Odds & Sods (1974)

I mentioned it off the top, but Odds & Sods is a borderline inclusion on this list. It’s a collection of leftovers—studio outtakes and last-minute cuts from other albums—that are culled from a 10-year period that’s looked at now as the Who’s most creatively fertile. Entwistle was the brainchild behind its assembly, stepping in to take over the project while Townshend and Daltrey were off filming the Tommy movie (more on that later). It was also created when the underground economy of bootleg concert tapes was starting to take off, much to the group’s chagrin, who saw it as a legacy detractor as much as a financial one.

So, on the one hand, I can appreciate the attempt to control the narrative. Exactly what Odds & Sods adds to said narrative, I’m still not entirely sure. The oldest cut on here is “I’m the Face,” which dates back to their High Numbers days, and the tracklist features material conceived during Townshend’s aborted Lifehouse project, whose recording sessions helped shape a lot of what you hear on Who’s Next. Along the way, you get official versions of live staples “Pure and Easy” and “Long Live Rock,” as well as the hard-hitting “Naked Eye,” which is arguably more potent than most of the material that made the grade out of the studio in 1969-70. Elsewhere, “Glow Girl” is one of several inclusions that serve as interesting half-baked snapshots, as multiple elements would later be recycled across multiple moments on Tommy.

If you can track down the original liner notes for Odds & Sods, they are hilariously revealing. Townshend appraises each track’s quality with such blunt bemusement that you question whether he actually thought the compilation was a worthwhile project to begin with. I don’t think any of the songs he skewers are anywhere near as bad as he makes some of them out to be. The quality floor is far too high. At this point in their story, the Who were too well-oiled a machine to descend into legitimately schlocky material. The more divisive question is how far above that bar the quality ceiling lies. Your answer will largely depend, I think, on how much of a fan of theirs you are to begin with.

8. The Who by Numbers (1975)

The Who By Numbers is a weirdly upsetting listen, and I mean that as positively as I can while still using the word “upsetting” as the main descriptor.

That’s because, in a first for the mid-70s iteration of the Who, they finally let listeners in and gave them a sense of the men behind the music, warts and all. Full of tales of struggles with alcohol (”However Much I Booze”), fame (”How Many Friends”), and women (”Dreaming From the Waist”), it features songwriting, once again primarily from Townshend, that’s so stark in its honesty that it works as disquieting, extemporaneous diary scribbling and darkly comedic tales you’d tell your friends or colleagues as a way to mask the pain, however thin that veneer may be. You’d be hard-pressed to find a cautionary tale about the rock star lifestyle that’s got this many laugh-out-loud lines in it.

Interior honesty wasn’t exactly a gear the Who were known for, and, even if they mostly pull it off, that lack of familiarity has led to this record being criminally overlooked in the decades since its initial release. Something like “Blue Red and Grey,” which is as light and airy as Townshend’s back catalog gets, belies a man who, deep down, is anything but whimsical. You can hear it in his vocal delivery and playing. It’s a song about grappling with depression by putting up a front, and it hurts to listen to on that level. And yet, in one of the singer/songwriter’s greatest sleight of hand moments, he shrouds that feeling in a composition so beautiful that most people hardly notice. That’s the point, after all. Let the listener in but don’t actually say the quiet part out loud.

Your mileage may vary depending on how much you enjoy and can sit with that approach to making music. If you find such confessional storytelling awkward to the point of being alienating, The Who By Numbers may not be the best fit. However, if you’re willing to sit with it and peel back multiple layers of oblique meaning, you’ll get a lot more out of this one than you might think. If you give it a try, there are some genuine arena-sized rockers to whet your appetite, including “Success Story,” an Entwistle joint, and “In a Hand or a Face,” which features Daltrey’s best moment on the album.

7. Face Dances (1981)

The first studio album released by the Who following Keith Moon’s passing, Face Dances is more of a continuation of Pete Townshend’s 1980 solo record, Empty Glass, than Who’s Next. On that record, the band’s leader sounds like he’s coming to terms with all the existential conflicts in this life. That’s not the same as resolving them, but there’s enough ethereal shimmer added to tracks like “And I Moved” and the excellent “Let My Love Open the Door” to at least nod in the direction of some kind of spiritual awakening. His songwriting evolved to match, becoming more polished and astute and somehow calmer, as if extracting these thoughts and feelings from his mind and soul was no longer such a labor-intensive exercise.

I bring all of this up because a lot of the criticism Face Dances drew on its initial release didn’t necessarily take this shift into consideration. Compared to most of their output from the 1970s, this LP is moodier, more oblique in its meaning, and, dare I say it, approaching subtlety? The Who? Based on the lyrical content, I have a feeling that’s what Townshend was going for in the first place. Deep down, the surviving original members knew you couldn’t replace Keith Moon, and, in the Small Faces’ Kenney Jones, they clearly didn’t try to. He’s more than capable of holding down the rhythms asked of him on this tracklist. But he’s a veteran of the industry, another consummate professional in the room alongside the others. The trade-off is the sense of danger that emanated from previous Who records.

Is that such a crime? The opener, “You Better You Bet,” is the best song off Face Dances and one of the strongest post-Moon singles the band released. Deeper cuts like “How Can You Do It Alone” and “Cache Cache” benefit from Townshend’s increased introspection, an ode to his continued growth as one of the genre’s consummate craftsmen. And yet, once you’ve tasted those morsels of near-greatness, you get a sense that there was an even more powerful story simmering just beneath the surface of this record. On that level, the biggest disconnect is Daltrey, who struggles at times with the more nuanced material he’s given. He’s a frontman who’s always painted in such broad brushstrokes that he can come off as smug or leering when the writing nudges him in a wounded, self-deprecating direction.

6. WHO (2019)

In almost every meaningful sense, 2019’s WHO is a two-hander. No disrespect meant towards drummer Zak Starkey and bassist Pino Palladino, both well-known artists in their own right, but this is a Townshend and Daltrey record. Their chemistry is undeniable here, a must for a tracklist that looks back more than it looks forward, but it’s also the first time in decades where they sound like they’re having a good time in the studio together. Those factors, combined with a long break following Endless Wire, fueled an improbable commercial success for the veteran Brits. WHO peaked in the penultimate spot on the Billboard 200 in the US and No. 3 on its UK equivalent, proving that, more than a half-century after they formed the Who, music fans still cared about what they had to say.

The best material here is as direct and emotionally clear-eyed as anything in their entire studio discography. The writing is almost uniformly witty, blunt, and, crucially, without an ounce of self-pity to be found. A lot of reviews got around of some version of, “If this is the last album,” yada yada, but Townshend and Daltrey clearly aren’t here for the ceremonial pats on the back. They know their heyday is behind them, and, as on “All This Music Must Fade,” that whatever residual pop culture cache they have left is getting close to its expiry date. Elsewhere, “I Don’t Wanna Get Wise” turns the same sarcastically realist lens on the aging process, how it shapes one’s relationship with mortality, and how decades touring one of the loudest shows in rock may have accelerated that timeline. There’s no waffling or circumnavigating, which I appreciate.

When the record stays in that register, it works surprisingly well. Unfortunately, it doesn’t stay there for its entire running time. The back third of WHO loses some of its heft and focus, which makes the runtime feel a bit overextended. Not perfect by any stretch, but there’s enough compelling songs in this collection to merit the warm critical and fan reception it’s received. Sometimes, I wonder if it’s 100% genuine, or merely an overreaction by people protecting an artist’s legacy simply because the album wasn’t a complete disaster. See the latest couple of Rolling Stones LPs, Hackney Diamonds and Foreign Tongues, as more recent examples of this dynamic in action (or not). Either way, this one’s worth a listen.

5. It’s Hard (1982)

Here’s where I go (ahem) hard against the consensus opinion: It’s Hard is good, y’all. Arguably very, very good.

I went back and read a bunch of contemporary reviews using the good old Wayback Machine, and let me tell you, early-1980s music critics had it in for this album. Some called it plodding and uncertain, a thinly veiled contractual obligation, while others didn’t lament the effort, just the execution. They couldn’t hack it anymore. They weren’t the same band, and that was the Who that they missed so terribly and blah, blah, blah. I was stunned to read these diatribes. Had I listened to the same record? Had I missed the cataclysmic trainwreck that somehow whizzed by my ears, undetected? All I heard was a band finding their center again and, in some ways, learning how to play together again.

Off the top, Jones sounds far more at ease behind the drum kit than he did on Face Dances. No longer saddled with the one-note “he’s not Keith Moon” appraisal, you can hear the renewed confidence on the arena-worthy “Athena,” where he’s the driver of one of the most slept-on tracks in the group’s history. Daltrey also bounced back nicely from what was a subpar outing on the same preceding album. He sings with a weight and urgency that hadn’t been in his work consistently since Who’s Next. See “I’ve Known No War” and “Cry if You Want” as prime examples of this dynamic in action. As a whole, It’s Hard makes a fascinating double feature with Face Dances. It’s two years later, but what a difference in execution.

The single strongest point is “Eminence Front,” featuring an Entwistle bass line that can groove for ages. Seriously, I’ve literally played this song four or five times in a row and that low-end refrain never, ever gets old. The vocal harmonies on the chorus are a lot of fun, too, and have only been enhanced by the recent digital remasters now available on most streaming services. The crowdpleasing elements have (finally) been given the presence in the mix they always deserved. That leaves Townshend, who continued to claw his way back from the brink lyrically, though perhaps less bracingly direct than he had been a year or so prior. If you want to hear something even wilder, check out All the Best Cowboys Have Chinese Eyes from 1982.

Now that’s a divisive record.

4. Tommy (1969)

There’s no disputing that Tommy is a legitimate music landmark. The first rock opera of its kind to gain worldwide commercial and cultural traction, it features a sprawling, 75-minute narrative built around a central character who’s deaf, dumb, and blind. Against all odds, he becomes a spiritual leader and travels far and wide, spreading his gospel. The structure alone spawned countless imitators in the decades that followed, most of which paled in comparison, which only reinforces how difficult what Townshend pulled off as a storyteller really was. To name-drop one example, I don’t think Pink Floyd have quite as successful a run as they did with concept albums if Tommy doesn’t set such a clear, ambitious blueprint for the future of rock and roll.

The best stretch of Tommy runs from “Amazing Journey” and “Sparks” through “Cousin Kevin” and “The Acid Queen.” The pacing across the entire sequence, the way the narrative builds momentum before releasing it in small, controlled spurts, all while delivering one dazzling solo or melody after another—it’s hard to top. But, if I’m being completely honest, the Who can’t keep that kind of momentum up for the album’s entire running time. Few bands could, if we’re honest. It’s not that anything is egregiously bad. It’s more that the seams holding the production together show more than they should. Some songs, and sequences in the eponymous film adaptation from 1975, exist more for logistical reasons than anything else.

“Pinball Wizard” is a prime example. It’s a really fun pub rock stomper with a conceit so delightfully nonsensical that you can’t help but sing along to a chorus about a man with Tommy’s physical limitations somehow being an exceptional pinball player. The same sequence in the movie looks like a million bucks, complete with a 20-foot-tall Elton John and a crowd of extras struggling to wave their hands side to side in unison. It works better as a glam rock vehicle for him anyway, which says a lot about its place in the Tommy tracklist. Is the album more enjoyable with a song like this in tow? Sure, you could argue that. But does the narrative and overall effect of the record lose any of its power if you cut “Pinball Wizard” and a few other bits of flab? I’d wager no, though I’m sure longtime fans may disagree.

Where does that leave us? Well, if you’ve never listened to Tommy all the way through, you owe it to yourself to do it at least once in your life. It’s one of those records you’ll want to carve out time for and give it your undivided attention while it’s on. Put the phones and other second screens away, get some coffee or tea and snacks, make sure your media device is fully charged, and let the waves of psychedelia hit your ears like you would a tide rolling into a pristine beach. Immerse yourself as best you can. Ditto for the film, which is replete with eye-popping imagery and more than a few regrettable haircuts. It’s considered a cult classic for a reason.

3. The Who Sell Out (1967)

Let’s keep the hot-take energy going: The Who Sell Out is, for my money, a stronger concept album than Tommy.

It’s strange and out-there and, due to its episodic nature, treated as more of a novelty project than a compelling long-form release. Cherry-pick the best moments and skip the rest kind of deal. But I couldn’t disagree more. Built around fake radio ads, this album’s framing device holds up much better than you might think 50-plus years later. By melding each individual moment into a fluid, evocative listening experience, the pacing and texture are much more harmonious than in their later releases. Tonally, it’s full of snark and aggression, taking aim at the dead-eyed capitalism that underpins how most people of a certain age encountered pop and rock music. Were the baked beans ad reads shoehorned in between the records DJs played or vice versa? Your answer will say a lot about your relationship to the notion of “selling out.”

Even if you were to strip all that meta-commentary out of the tracklist, you’d still be left with an ace collection of songs, up there with the Who’s best melodic achievements. On one side of the intensity dial, you have “I Can’t Reach You” and “Sunrise,” important reminders that, even with an increasingly anarchic reputation, the British foursome could land material with the softest of touches. They, along with a few other moments on this LP, have more in common with the Monkees or the Beach Boys, two comparisons that may not come up that frequently in discussions about the Who, which I think is a shame. Their range is the most underrated part of their collective talent.

On the other side of that intensity dial lies “I Can See for Miles,” a jaw-droppingly unhinged, unrelenting rock song. It rightfully ranks among their finest singles, due in no small part to Moon’s performance on drums, which rivals anything else he put on tape while recording with the band when it comes to sheer force of will. It earned its critical reputation at the time as the “heaviest” song around, inspiring one Sir Paul McCartney to, sight unseen (or, in this case, unheard), write a Beatles classic that would top it. “Miles” famously underperformed on the UK singles chart compared to expectations but peaked inside the Top 10 on both the Billboard Hot 100 and its Cashbox counterpart. The US success was attributed to Moon’s stunt on The Smothers Brothers Comedy Hour, where he set off an explosive during the taping.

How very rock and roll of him.

2. Who’s Next (1971)

The Who’s most beloved album, Who’s Next, rose out of the ashes of a much more immersive, ambitious project. The recording sessions were originally intended to lay the groundwork for Lifehouse, a multimedia extravaganza that, for 1971, was way ahead of its time. And if you think Tommy was trippy, just listen to Townshend describe the narrative concept:

“In Lifehouse, humanity would survive ecological disaster by living in pod-like suits, amused and distracted by sophisticated programming delivered to them by the government,” explained Townshend. “Because of its potential to awaken the dormant masses, rock music would be banned.”

The plot supposedly included a roadie named Bobby who, harnessing technology that sounds a lot like the algorithms that drive streaming services, devises sounds curated to each individual based on their astrological sign. Unsurprisingly, the concept didn’t sit well with the rest of the band. “It didn’t make any sense,” Daltrey recalled. “None of us could grasp it. But it did have some good ideas in it. The one I picked up on was that if we ever did find the meaning of life it would be a musical note. I thought that was a great idea.” A few starts and stops later, the band eventually made it into Olympic Studios in London to salvage what material they could from Townshend’s growing glut of material and package it as a more conventional Who album. It would go on to become one of their greatest triumphs.

If you’ve interfaced with the classic rock industrial complex at any point in the past 40-50 years, you know the bookends. “Baba O’Riley,” with that genuinely iconic arpeggiated synth opening, remains a transcendent portrait of generational disillusionment. “Won’t Get Fooled Again” is the science-fiction knockout punch, closing the record with a stunning eight-and-a-half-minute pressure build that only releases when Daltrey’s towering shriek (side note: If you want to feel exhausted after watching a YouTube video, peep Chad Smith of the Red Hot Chili Peppers bash through a cover of “Fooled”). Both serve as testaments to Townshend’s stature as a proficient tinkerer with cutting-edge technology and the group’s ability to pack an unforgettable wallop around those elements. The songs sound like controlled chaos but are also deceptively intricate in their detailed arrangements. The wilder the exteriors, the more deliberate the structural choices.

What gets underplayed is how strong the rest of Who’s Next is. “Bargain” and “Going Mobile” are two of the best pure rock songs in the band’s arsenal, with taut, focused playing and direct, utterly charismatic performances from Daltrey. “Love Ain’t For Keeping” has always been one of my favorite Who cuts, featuring some insanely catchy acoustic riffing from Townshend, and “Behind Blue Eyes” comes through with one of the most memorable gear shifts in the genre’s history. Every time I hear the latter’s switch-up moment, it never fails to give me goosebumps. The same could be said for the tracklist as a whole, especially as I get older and hone in on specific aspects of the album with each listen. From Moon’s polyrhythmic tornadoes to the power chords that hit you like a freight train, there isn’t a dull moment to be found here.

1. Quadrophenia (1973)

Quadrophenia takes the top spot in the Who’s discography because it represents the moment when they perfected the rock opera as both a rock delivery system and a sonic vehicle for utterly cinematic creative expression.

The boxes are ticked in favor of this being the band’s apex pretty much across the board. The writing from Townshend is more mature and cohesive, Entwistle and Moon are at the very top of their respective games, and it’s the best outing that Daltrey’s ever had on record with them. More than those individual aspects, the heft of the core narrative, centered around a young mod named Jimmy who’s unable to fit in no matter where he turns, earns every ounce of catharsis it builds to.

Here’s a snippet from my original album review of Quadrophenia, breaking down some of my favorite moments:

“Those familiar with the Who’s hard rock prowess will find plenty to love here, from [Moon’s] thundering intro on “The Real Me” to the prog-meets-honky-tonk “5:15” to the punk precursor “I’ve Had Enough.” But, as excellent as those records are, the jewel in Quadrophenia’s crown is the closing 20 minutes. Beginning with “Bell Boy,” protagonist Jimmy’s worldview shifts dramatically as he realizes how limiting the mod lifestyle can be. These revelations lead to “Doctor Jimmy,” one of the angriest songs the Who ever committed to tape, which sees the character descend into violent outbursts as he hits his emotional rock bottom. Then, when the proceedings feel like they’re getting too dark and unsettling, the clouds part, and the sun shines through on “Love Reign O’er Me,” [one] of the best redemption moments in the classic rock canon […]”

It’s worth mentioning that Quadrophenia was also turned into a feature film in 1979, with the biggest difference between it and the Tommy adaptation being that it’s not a musical. The band doesn’t appear on screen at all, either. Instead, it’s a gritty, quasi-neorealist drama with an unbridled firecracker energy. As a portrait of male teen angst, it gets a lot right, from the confused, misguided romantic impulses to the violent outbursts that always threaten to bubble up in the dark alleys of working-class neighborhoods. I dug into my collection and rewatched most of an old copy I had, and it was a lot more poignant than I remembered. It’s not a direct translation of the group’s masterpiece of a concept album, but more of a companion piece, putting vivid images to the gut-wrenching feelings of loneliness and alienation that have become the hallmark of Townshend’s persona as a songwriter.

Which album still hits you hardest? Drop it in the comments.

Genre: Arena Rock, Hard Rock, Pop Rock
Label: Epic Records
Release Date: August 25, 1976
Vibe: 🎸🛸

👉 Click the GIF to stream the album on your favorite platform:

It’s one of the great mad scientist origin stories in rock and roll history.

In 1976, Tom Scholz was an MIT grad working as a product design engineer at Polaroid. He was a technical wizkid, specializing in audio and tape recording technology, with nearly a dozen patents to his name. He was also just 29 years old. He hadn’t even picked up a guitar until his early-20s, after becoming obsessed with early British Invasion groups like the Kinks and the Yardbirds. He quickly became a self-taught multi-instrumentalist, gigging with bar bands in the Boston area, which led to him building a tiny studio in Watertown where he began relentlessly tinkering with ideas, re-recording tracks again and again in search of the “perfect” rock song. It became such a fixation that he used the money he’d saved for a down payment on a future house to purchase a professional 12-track tape recorder. It was all or nothing.

It’s remarkable that Scholz kept soldiering on in this way. For the previous five years, he’d made demo tape after demo tape supported by a band he’d been playing with locally, Mother’s Milk, and received one rejection letter after another. RCA, Capitol, Atlantic, Elektra, and Epic were among the labels that first passed on what Scholz was putting out into the universe, even though those tapes featured early iterations of several tracks that would make it onto Boston. Due to the lack of progress, Mother’s Milk supporting members came and went at various points, including singer Brad Delp, whose day job back then was as an assembly line worker at an electric coil factory. Eventually, Scholz was asked to audition for Epic with a full band, to prove that the mad scientist act would translate to live venues. And, even after they passed that, the label wanted the group to decamp to Los Angeles and record all their songs with a different producer.

Naturally, Scholz balked at this request and had producer John Boylan deploy as many smokescreens as possible to make the Epic brass think they were complying. In reality, except for “Let Me Take You Home Tonight,” which was recorded in Los Angeles as a decoy of sorts to appease CBS, Epic’s parent company, the vast majority of what you hear on this classic record, which turns 50 years old this week, was tracked on Scholz’s equipment, which was either consumer-grade or something he custom-built, in the same environment as the demo tapes. The biggest difference was Delp’s soaring vocals, which were overseen by Boylan and partially saved during the mixing process, during which Scholz kept pushing the guitar much higher in the mix than anything else. After all that effort and painstaking attention to detail, it looked like everyone’s life would more or less return to normal.

Here’s Scholz on the moment that all changed for him, via a 2024 interview he did with the MIT Technology Review:

“Honestly, I thought the recording I made in 1976 was going to be forgotten by the beginning of 1977,” he says. He was just hoping to get the song on the radio so he could get gigs in local clubs with a song people recognized. “I actually didn’t realize there was anything serious happening with my album until I was working in my back room [at Polaroid]—I had a secret back room, sort of like a boiler room, in the bowels of the building in Tech Square—and somebody comes running and says, ‘Hey! Your song’s playing in the drafting department!’”

I’ve seen Boston’s music, and specifically the songs that make up this tracklist, described as some version of dead-eyed “corporate rock,” even though the nuts and bolts it uses to build out its sound have little to nothing to do with the low-hanging rock clichés from the mid-1970s. In the Rolling Stone album guide, “More Than a Feeling” was touted as the hit that “ushered in the long, cold winter of arena rock; Boston’s soaring combination of high-tech metal guitar punch and smooth pop vocal hooks quickly became the cornerstone of Album Oriented Radio.” Perhaps that’s true on some level, but it also shortchanges the incredible heft of Delp’s lead vocal, which showcases his four-octave range to devastating effect, particularly on the final bridge. I remember getting shivers hearing him hit those notes when I first discovered the album in my early teens. It’s also a production marvel, featuring skull-rattling guitar work that knows exactly when to lean in and when to pull back.

That calibration runs through the rest of the LP’s first side, even as the songs get progressively stranger. “Peace of Mind” features acoustic guitar playing that slices through the rest of the heaviest arrangement on the album, giving it genuine levity. “Foreplay/Longtime” is the oldest Scholz composition on the record (he started writing it in 1969 while still at MIT) and definitely the most out-there. The chaotic first three minutes mimic the exhilaration that bubbles quicker and quicker in the former scenario described in the title, while the vocal harmonies give the post-coital second half an unexpectedly poignant quality. I’m not sure it’s meant to, but again, how can the human spirit have any other emotional reaction to Delp’s singing? Elsewhere, you have some bar band throwback energy (”Smokin’”), proto-power pop (”Something About You”), and a gorgeous moment in “Hitch a Ride,” which includes an intro so understated but precise that it threatens to take your breath away.

In case you didn’t know, Boston was an absolute commercial monster. It peaked at No. 3 on the Billboard 200 and remained on the chart for over 130 weeks. It sold two million copies by January 1977, then one of the fastest-selling debuts in American rock history. The album also held the title of best-selling US debut ever until Guns N’ Roses’ Appetite for Destruction arrived in 1987. Now certified 17 times Platinum, it’s one of the most popular records of its era, despite not getting a ton of critical respect. Its only Grammy nomination was for Best New Artist, a distinction it lost to (checks notes and shudders) the Starland Vocal Band. That’s right: the “Afternoon Delight” guys. Seriously. That happened. Also, I want to pause and acknowledge that song as one of the worst songs about having sex ever written. It’s not titillating, it’s not even entertaining. The fact that the Academy voters decided that this folks would have a more impactful future than Boston is just inconceivable. Anyway, I digress.

Fun fact: This was Boston’s peak as a band, too. They became the first act to make their New York City debut at Madison Square Garden and toured successfully for many years after that, but their studio material took a serious quality dip soon after their debut album. 1978’s Don’t Look Back tried to run the formula back for a direct sequel with uneven results, while 1986’s Third Stage downshifts into full-on schmaltz mode. Delp died by suicide in 2007 and, after multiple comeback attempts with different lineups, the group hasn’t toured since 2017. But this album’s commercial performance meant Scholz did more than alright for himself. He used the proceeds to found Scholz Research & Development, the entity through which he commercialized his recording inventions and helped shape the guitar sound of 1980s rock production. Once a tinkerer, always a tinkerer.

Where does Boston’s music rank among your 1970s favorites? Let everyone know in the comments.

Genre: Worldbeat, Pop, Folk Rock

Label: Warner Bros. Records

Release Date: August 25, 1986

Vibe: 🌍🪗

👉 Click the GIF to stream the album on your favorite platform:

I remember my first reaction to Graceland being incredulity.

“This is Paul Simon?” I thought. The folksy singer-songwriter guy? The “Mrs. Robinson” and “Sound of Silence” guy? The “lie-la-lie” guy? He made this? My early-teen brain couldn’t wrap my head around the incongruencies that kept jumping out of my headphones and into my brain, song after song after song. Sure, there were recognizable elements of pop and rock sprinkled throughout the tracklist (though, in my defense, a lot of those tropes weren’t ones that Simon had explored with any consistency prior to this LP), but it didn’t sound like any pop or rock album I’d ever encountered. As a kid who grew up in suburban Canada, who had no concept of any localized African musical traditions or legacies, South African styles like isicathamiya and mbaqanga may as well have been beamed in from another dimension. I was perplexed by Graceland, but also utterly enthralled. These songs were thrilling and spiritual in a way I’d never felt before, causing my blood to pulse with excitement.

Initially, all of that buzz came from the ultra-seductive surface layers. The irresistable rhythms, anchored by the myriad percussive elements including Bakithi Kumalo and Ray Phiri’s magnificent work on the bass and guitar, respectively, were elite. The melodies were crisp. The lyrics, arch though they still were, were a lot of fun. It wasn’t Simon at his most intellectualized or self-serious, which certainly helped as a hook to get me more interested in his larger oeuvre, but, as I got older and absorbed more and more music history, the more impressive Graceland became. I’m not sure it’s an indictment of those first impressions. Not exactly. Maybe more a roundabout compliment to Simon’s ability to couch deeply human themes about loneliness, losing your sense of place in the world, and ultimately finding your way in moments and locales you least expected to. For example, I used to think “You Can Call Me Al” was a breezy, easily dismissable farce. Now I hear lines like, “He sees angels in the architecture/Spinning in infinity, he says, ‘Amen,’ and, ‘Hallelujah,’” and I hear a man who’s finally had that lightning bolt moment.

If you wind the clocks back to 1984, Simon needed one such moment, too. His most recent LP to that point, the previous year’s Hearts and Bones, initially intended as a joint project with Art Garfunkel, had sold poorly and, combined with a collapsing marriage, had sent him into a depression. Suddenly, he was 43 years old with a solo career that plenty of pundits thought had reached the end of the road. According to his detractors, Simon’s signature sound had nowhere else to go and, based on where he went next, maybe they were right. The lightning-bolt moment that sets the Graceland story in motion was a cassette tape that arrived through an SNL connection: musician Heidi Berg. She had been a member of the house band when Simon was a regular, and was the one who turned Simon on to mbaqanga, Black African street music tied to Johannesburg’s Soweto township. Berg had acquired a bootleg mixtape of obscure songs in this style and lent it to Simon, who quickly became obsessed.

”I never would have gotten into this whole thing if I hadn’t vigorously pursued the origins of a copy of a copy of a cassette,” Simon explained to Rolling Stone two years later. He tracked down the musicians and flew to Johannesburg with his longtime engineer Roy Halee. Crucially, he brought no songs with him to the studio there. The sessions in South Africa yielded rhythm tracks and grooves recorded with Kumalo, Phiri, drummer Isaac Mtshali, the Boyoyo Boys, Joseph Shabalala, the a cappella group Ladysmith Black Mambazo, and several others. He also recorded material for Graceland in London, New York, Los Angeles, and Lafayette, Louisiana, with a cast that included (but is not limited to) Linda Ronstadt, Los Lobos, the Everly Brothers, and Senegalese percussionist Youssou N’Dour. “I didn’t want it to be just an African album,” he told the magazine. ”I wanted to say, ‘Look, don’t look upon this as something so strange and different. It actually relates to our world.’”

So, look, I’ve never thought that Simon’s intentions were anything but positive and even noble to a certain degree. When asked if the songs on Graceland were political, he said that the furthest thing from his mind was using his platform to whitewash their plight. He described his mentality simply: “They play their best, I’m gonna play my best.” While all that may be true, the fact remains that Simon traveled to South Africa in 1985 during the UN’s cultural boycott of the apartheid regime. He did not consult the African National Congress (ANC) and acted only on a green light from the South African Black musicians union. To his credit, he’s discussed this aspect of the album’s backstory ad naseum over the years and has never deflected. He says he paid the Johannesburg session participants three times New York union rates, credited co-writers, and ultimately gave South African artists a global platform they arguably wouldn’t have been able to access under apartheid. It’s a legit counter-argument. But legit is also how I’d describe the consistent criticism that he made those decisions for himself, on a timeline that suited his creative instincts rather than the political strategy of people fighting for their survival. I’m not here to tell you how to think or feel about that. I only want to be real about both sides of the narrative.

Let’s return to the music and ask the easy question: What makes it so compelling, 40 years later? In many ways, they invert what had been a reliable Simon formula, which meant starting from the lyrics and moving outward. The arrangements were built to serve the words, but here, it was the other way around. More often than not, the rhythm was locked in before Simon knew what the song was even about. That inversion invited a different, almost experimental kind of songwriting, one that’s far more fragmented and imagistic, and way less linear. There’s still a lot of personal material to sift through, but where those ideas would’ve previously manifested as confessions, they instead become characters in motion, obliquely gesturing at the emotional undercurrents rather than taking your hand, pointing at the mirror, and spelling everything out for you. In a previous life, a track like “The Boy in the Bubble” is pitched at a much different tenor and I’d argue it’d be worse off. Simon rattles through cable news items in a way that sounds like a CNN fever dream: a bomb in a baby carriage, lasers in the jungle, and so forth. “These are the days of miracle and wonder,” the chorus insists, even as you sit there with an open head wound.

“Diamonds on the Soles of Her Shoes” pushes even us further out of Simon’s comfort zone. Ladysmith Black Mambazo opens a cappella in Zulu for a full minute before Simon enters, his voice playfully bouncing off of an arrangement that draws from doo-wop, gospel, and mbube simultaneously and without sounding like a mismatch. If you sit and listen to it with the purpose of breaking it into as many little sonic fragments as you can in real time, it’s astounding how well everything holds together. The quieter, subtler moments are exceptional, too. “Under African Skies” paints on this dreamy, expansive canvas, to the point where you can close your eyes and picture yourself lying there, under the eponymous starry night. “Homeless” is another stunner, using powerful vocal harmonies to stand with the dispossessed, all but forgotten as collateral damage during apartheid. The title track, a contender for this album’s best, closes the narrative circuit. The line that still carries weight is the one that’s careful not to overpromise: “I have reason to believe we all will be received in Graceland.”

Per my research, it doesn’t seem like anybody expected much when Graceland arrived in August 1986, including Simon himself. It climbed slowly on album-oriented radio and word of mouth, eventually reaching No. 3 on the Billboard 200 in March 1987, a chart where it stayed for 101 weeks. It won multiple Grammys, including the biggies for Album of the Year and Record of the Year for the title track, making Simon one of only three artists to have won Album of the Year three times. To date, Graceland has sold over 14 million copies worldwide, making it Simon’s biggest success by a country mile. Even the ANC later acknowledged that the LP had increased global awareness of South African music and its artists. Shortly after, the UN removed Simon from its boycott violators list, and Ladysmith Black Mambazo became international figures thanks to the exposure this album provided. Its fingerprints are still audible downstream, in everything from Vampire Weekend’s debut to Burna Boy’s global crossover.

What’s your favorite Paul Simon song? Shout it out in the comments.

Most of the time, I don’t know exactly where it comes from, nor do I plan whose writing makes it into my own prose on any given day. Honestly, I’m more focused on putting one foot in front of the other and keeping the content calendar moving in the right direction. Some weeks are better than others, but if nothing else, the work gets done.

Whatever growth my writing has enjoyed happens between those lines.

All that said, I find myself returning to familiar sources for inspiration time and again. Not to intentionally rip them off, but simply to cleanse my creative palette with prose I consider to be next-level. I thought I’d share seven figures whose oeuvres loom largest in my mind’s eye and from whom, subconsciously or not, I’ve undoubtedly picked up a trick or two over the years.

Before diving in, a brief reminder to do all the usual engagement things, including sharing this post with friends, family, or pets if you enjoy it (it’s the best, and totally free, way to help this newsletter reach more people worldwide)

Let’s begin:

1. Roger Ebert

Ebert was the first critic who I read for his writing and not for this thoughts on the latest movies or film culture. He was a great critical thinker, don’t get me wrong, and often ahead of his time, but he was an even better writer.

Not a massive revelation about a man who won a Pulitzer in 1975, but somehow, maybe because he’s still best known for his work in front of the camera, it’s a quality that consistently gets overlooked.

Here are some of my favorite Ebert lines:

From his review of The Squid and the Whale:

“ I don’t know what I’m supposed to feel during ‘The Squid and the Whale.’ Sympathy, I suppose, for two bright boys whose parents are getting a messy divorce. Both parents are writers and use words as weapons; the boys choose sides and join the war.”

From his review of My Neighbor Totoro:

“Here is a children’s film made for the world we should live in, rather than the one we occupy. A film with no villains. No fight scenes. No evil adults. No fighting between the two kids. No scary monsters. No darkness before the dawn. A world that is benign. A world where if you meet a strange towering creature in the forest, you curl up on its tummy and have a nap.”

And, from the last review he ever filed, for To The Wonder:

“Why must a film explain everything? Why must every motivation be spelled out? Aren’t many films fundamentally the same film, with only the specifics changed? Aren’t many of them telling the same story? Seeking perfection, we see what our dreams and hopes might look like. We realize they come as a gift through no power of our own, and if we lose them, isn’t that almost worse than never having had them in the first place?”

Simple, approachable prose that was consistently evocative, heartfelt, and often very funny (especially in his infamous one-star reviews). After rereading his work over and over again in my life, the same lesson always resurfaces: A critic’s job is not to deliver a verdict but to help the reader understand what the experience actually was.

Explain what it does to you, and then earn that claim.

2. Seymour Hersh

When I think of fearless, unflinching reporting, I think of Seymour Hersh.

He’s undeniably one of the most important investigative journalists of the last 100 years. He’s broken stories like the My Lai Massacre, the Watergate fallout, and Abu Ghraib, all with tenacious, occasionally pugnacious methods. Like any other writer, you can agree or disagree with the “how,” but you can’t deny the brilliance of the “what” when it legitimately shifts the national conversation.

So why does Hersh belong on this list of music criticism influences? One big reason is how economically he can establish a vivid setting and palpable stakes. Here’s the opening paragraph from his Abu Ghraib piece, which does a tremendous amount of work in two straightforward sentences:

“In the era of Saddam Hussein, Abu Ghraib, twenty miles west of Baghdad, was one of the world’s most notorious prisons, with torture, weekly executions, and vile living conditions. As many as fifty thousand men and women—no accurate count is possible—were jammed into Abu Ghraib at one time, in twelve-by-twelve-foot cells that were little more than human holding pits.”

There’s also the fact-based narrative aspect of his writing that’s rubbed off on most of what I publish in this newsletter. The formula is simple: Go find the thing and use the data to augment what you’re saying. Don’t gesture at production techniques when you can name the specific studio where the album was recorded. Don’t paraphrase critical reception when the actual review is one search away. Don’t attribute commercial success to “the cultural moment” when the chart data is right there.

The facts exist. Go get them.

Also, for those interested in learning more about Hersh’s extraordinary career, I highly recommend the Netflix documentary about him.

3. Hunter S. Thompson

To clarify: I’m referring to Hunter S. Thompson the gonzo journalist, not Thompson the novelist (though Fear and Loathing in Las Vegas is a book I’ll return to every couple of years and learn something new from a craft perspective).

More than any other reporter (including a couple on this list), Thompson pioneered the writer’s point of view as a feature, not a bug. He wasn’t a violet who shrank under the auspices of alleged objectivity. Instead, he made his reactions to the action in the story, not necessarily the action itself. It’s a key difference that, as much as it’s flourished in the age of Substack and, increasingly, in a post-mass-media world, I haven’t read anyone who has leaned as hard into this profile as Thompson.

His 1970 Scanlan’s Monthly piece “The Kentucky Derby Is Decadent and Depraved“ is the purest example of what made him an essential voice. It’s also an eye-opening structural guide for anyone who wants to reframe their writing to make it more distinctive and personal. It opens with an act of pure self-observation and never positions him as a neutral bystander. In music criticism, your reaction to an album isn’t something to bury or hedge around. It’s the whole reason someone’s taking the time to read what you have to say. Make your case.

One of my favorite passages from that piece:

“The next day was heavy. With 30 hours to post time I had no press credentials and — according to the sports editor of the Louisville Courier-Journal — no hope at all of getting any. Worse, I needed two sets; one for myself and another for Ralph Steadman, the English illustrator who was coming from London to do some Derby drawings. All I knew about him was that this was his first visit to the United States. And the more I pondered that fact, the more it gave me fear. Would he bear up under the heinous culture shock of being lifted out of London and plunged into a drunken mob scene at the Kentucky Derby? There was no way of knowing. Hopefully, he would arrive at least a day or so ahead, and give himself time to get acclimated. Maybe a few hours of peaceful sightseeing in the Bluegrass country around Lexington. My plan was to pick him up at the airport in the huge Pontiac Ballbuster I’d rented from a used car salesman named Colonel Quick, then whisk him off to some peaceful setting to remind him of England.”

4. David Foster Wallace

Like Thompson, I’m focusing on Wallace the essayist, not the novelist. At the peak of his fame, he was more than a celebrity. In interviews like this one he gave to Charlie Rose, he’s fascinating to just sit and listen to. And, though his intellectual heft could easily blind those unprepared for it, his short-form work was never anything less than accessible and, more often than you might think, uproariously funny.

A well-known example is “Consider the Lobster,” published in Gourmet in 2004. The feature turns a Maine Lobster Festival assignment into a genuine ethical inquiry. He couldn’t stop asking whether boiling an animal alive for your dinner is something you should just keep doing. “Up, Simba,” his reporting on the 2000 McCain campaign follows the candidate’s bus tour and uses accumulating detail to make a complicated argument about authenticity in politics.

Both pieces showcase an instinct I’ve tried to add to my own writing over the years: follow the question past the comfortable stopping point. An example, from “Lobster:”

“Is it possible that future generations will regard our present agribusiness and eating practices in much the same way we now view Nero’s entertainments or Mengele’s experiments? My own initial reaction is that such a comparison is hysterical, extreme — and yet the reason it seems extreme to me appears to be that I believe animals are less morally important than human beings; and when it comes to defending such a belief, even to myself, I have to acknowledge that (a) I have an obvious selfish interest in this belief, since I like to eat certain kinds of animals and want to be able to keep doing it, and (b) I haven’t succeeded in coming up with a compelling argument for why this belief is true [...]”

Also, if you haven’t yet, getting through Infinite Jest is a rite of passage for any serious scribe.

5. Nora Ephron

Nora Ephron is flat-out one of the best writers who ever lived. Funny, insightful, and, most importantly for this conversation, consistently surprising in the way she constructs her prose. I would read her essays and think I knew where the end of a sentence or paragraph was going, but she’s one of the masters of the quick left turn or, if you prefer, left hook to the jaw. She could be writing about the smallest, occasionally mundane topics (a ruined dinner party, forgetting things, etc.), but everything I’ve read of hers has been nothing less than enthralling.

It’s a shame most people only know her as the Queen of Rom-Com, having written the screenplays for When Harry Met Sally, Sleepless in Seattle, You’ve Got Mail, and many others. It feels weird to call Ephron underrated, but if you take into consideration the vast amount of material she published outside the confines of Hollywood, I don’t think her legacy is fully appreciated either. Her pieces on women, food, and media still read as current, even if some first saw the light of day more than 35 years ago.

A couple of my favorite bits of hers …

From Crazy Salad: Some Things About Women:

“I wish he were better at hailing taxis than I am; on the other hand, I realize that expectation is culturally conditioned, utterly foolish, has nothing to do with anything, is exactly the kind of thinking that ought to be got rid of in our society; on still another hand, having that insight into my reaction does not seem to calm my irritation.”

From “A Few Words About Breasts:”

“But you could see breasts; they were there; they were visible. Whereas a girl could claim to have her period for months before she actually got it and nobody would ever know the difference. Which is exactly what I did. All you had to do was make a great fuss over having enough nickels for the Kotex machine and walk around clutching your stomach and moaning for three to five days a month about The Curse and you could convince anybody.”

I have a saying about writers as effortlessly prolific as Ephron: If I had a tenth of the talent they do (or did, in her case), I’d have a very, very good career.

6. Anthony Bourdain

In a revelation that will likely not come as a surprise to anyone who’s followed this newsletter for a longer period of time, I’ve always wanted to write about anything, but music and culture in particular, the way Anthony Bourdain wrote about food and the life of a bon vivant.

The word “authentic” gets thrown around a lot in this discipline, and I’m a little dubious of the concept, since the largely anonymized, faceless nature of this profession means writers can, with practice, fake it pretty well. That wasn’t the case with Bourdain. His incisive, no-BS way of looking at the world could be scathing to the point of making readers and watchers of his TV shows uncomfortable, but that was the point. He had no patience for protecting consensus opinions or softening his views to “fit in.” He was always unapologetically himself.

That’s a big part of the reason why, when he doled out praise and wisdom, it meant something. A mass audience listened to him and, long before the digital nomad lifestyle became normalized as a way to set foot in as many countries as possible, found within themselves the courage to push beyond what they thought was “safe.” His enthusiasm for a bowl of noodles in Hanoi or roasted lamb in Marrakesh stemmed from open-hearted curiosity and a welcoming spirit. You can’t manufacture that in the same way you can “authenticity.”

His books are a reminder of how much of a game-changer he was in the literary community. Kitchen Confidential, which is, without a doubt, one of the most formative books I’ve ever read, taught me more about cultural observations than any music writer could. There’s a directness in the way he speaks to you on the page that cuts to the core of what he really believes.

Take this example:

“Garlic is divine. Few food items can taste so many distinct ways, handled correctly. Misuse of garlic is a crime... Avoid at all costs that vile spew you see rotting in oil in screwtop jars. Too lazy to peel fresh? You don’t deserve to eat garlic.”

He had a saying (and I’m paraphrasing): Accept offers of hospitality without fear or judgment. We should all do the same with music and art.

7. Ray Ratto

Ray Ratto spent four decades covering Bay Area sports for the San Francisco Examiner, the San Francisco Chronicle, and NBC Sports Bay Area. He’s now one of the many prolific and notable names plying their trade at Defector, a site I proudly subscribe to. Imagine if a seasoned, erudite columnist formulated every thought the way a Las Vegas insult comic would, and you have a pretty good idea of Ratto’s prose style.

A couple of brief samplings, courtesy of the Ringer’s 2019 profile on Ratto:

“Ratto on the NCAA: ‘The Association defends its trademark prerogatives down to the last soda cup with an almost Serbian zeal.’”

“Ratto on an NFL Sunday: ‘Forty Niners–Bucs at 10, Jets-Raiders at 1:30. As for church, family obligations, or just lifting your bloated and ever-widening seater off the couch, you’re on your own.’”

His refusal to romanticize his own trade, or the professional athletes that trade was prone to building up and tearing down in equal measure, taught me a lot about how not to overdose on the “fan” aspect of music criticism. Praise can often be a cop-out in either field, an easy substitute for specificity. Let’s call it reaching for the lowest-hanging cliché instead of admitting what you actually think. Ratto continually proves that nostalgia is not analysis, and treating a genre’s past as automatically superior to its present is its own kind of pseudo-authority.

I’ll leave you with another excerpt of his that builds on that notion and lands a handful of great zingers along the way:

“[He] was a breathtakingly literate, cultured and erudite man who just happened to look like the Czar Nicholas II, wear the chest-harness microphone (to keep his hands free) like a stevedore, drive cars with millions of miles on them that predated even chrome, and dress like the Ancient Mariner. If he had socks, he kept them around only for special occasions. Frankly, to call him a renaissance man does more justice to the Renaissance than it does him. He was a character because he had character, not because he developed one for career reasons.”

Which writers have shaped how you write and/or how you hear music? Drop yours in the comments.

When Billboard published its first SoundScan-powered album chart in May 1991, the music industry had a brief, collective panic attack.

Within weeks, Skid Row was debuting at No. 1 on the Billboard 200. By September, Garth Brooks’s Ropin’ the Wind became the first country album in history to enter the pop chart in the top spot. He did that a week after Metallica elbowed their way into the No. 1 position with their self-titled “Black Album,” which eventually went 16x Platinum (the Brooks record hit 14x).

For context, only six LPs had accomplished that feat in the chart’s previous 35-year history. Elton John was the only artist to do it more than once.

Here’s the Ringer’s Rob Harvilla on the SoundScan shift from his excellent 2021 write-up:

“[The] magazine started counting album sales with scanners and computers and whatnot, and not just calling up record stores one at a time and asking them for their individual counts, often a manual and semi-accurate and flagrantly corrupt process. This is the record industry’s Moneyball moment, its Eureka moment, its B.C.-to-A.D. moment. A light bulb flipping on. The sun rising. We still call this the SoundScan Era because by comparison the previous era might as well have been the Dark Ages.”

The shift infiltrated the Hot 100 that November, with Billboard adopting both SoundScan sales data and BDS airplay tracking to determine the most popular songs in America. The combined effect wasn’t necessarily a more “accurate” chart so much as a completely different picture of who was buying and listening to certain types of music. Labels had to reckon with the fact that a massive suburban and rural consumer base now wielded incredible power in the pop marketplace.

Marketing budgets shifted. Distribution strategies changed. And what counted as a “hit” mutated overnight. For the first time, pop, country, hip-hop, R&B, rock, and Latin singles competed for the same real estate on roughly equal footing. The results were insanely memorable.

As with every other installment in this Billboard Hot 100 series, this isn’t your standard “best of” list. It’s a collection of 20 songs that left the greatest impression on me as a music nerd, and also happened to hit No. 1 between 1990 and 1999. One song per artist only, so acts like Mariah Carey, Whitney Houston, and Janet Jackson can each occupy only one slot.

Also, a quick reminder that plenty of great 90s songs couldn’t possibly have made this list because they never topped the charts. A trio of rock examples includes:

• “Smells Like Teen Spirit” by Nirvana, which peaked at No. 6

• “Losing My Religion” by R.E.M., which topped out at No. 4

• “Creep” by Radiohead, which stalled at No. 34

If you’re new here, the 1960s, 1970s, and 1980s lists are already up. Paid subscribers also get the companion playlist for each decade (one-song-per-artist rule there, too). Skip to the playlist and/or upgrade your subscription tier if you’re down for bonus content you can listen to.

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In chronological order, let’s go:

1. “Nothing Compares 2 U” by Sinéad O’Connor (1990)

What the late, great Sinéad O’Connor does with her voice on this track is worth the price of admission on its own.

Whether she’s operating at a pained semi-howl or an almost-whisper, the nakedness of her performance adds layer after layer of emotional heft to the lyrics that, as big a fan as I am of his, no one in Prince’s extended universe could hold a candle to. The Purple One wrote the song in 1985 for his then-side hustle, The Family, one of several acts in his Minneapolis stable. That version came and went without making any commercial dent. But by stripping nearly everything out of the arrangement except the synths and strings, producer Nellee Hooper and O’Connor turned a once-forgotten B-side into an unforgettable heartbreak anthem.

The music video, directed by John Maybury, only adds to this song’s power. It’s essentially just O’Connor’s face against a dark background. Her gaze, held with piercing eyes framed by pale skin and her customary shaved head, is utterly transfixing, looking into your soul and daring you to look away. The tears near the end were real and unplanned, reportedly the product of O’Connor remembering her mother, who died in a car accident in 1985. In a decade that, as we’ll see, was defined by high-budget, high-concept music videos, this level of simplicity was its own kind of statement. When I first saw the video, I was deeply touched. I couldn’t get it out of my head for several days afterward.

It’s hard to believe that O’Connor was only 23 when “Nothing Compares 2 U” became a massive hit. This record alone sold over 2.5 million copies in the US and propelled its parent album, I Do Not Want What I Haven’t Got, to the top of the Billboard 200. Unfortunately, she’d never get her due as a pop act. Two years later, following her infamous Pope-photo-ripping incident (which I discussed in detail here), she was essentially shunned by the North American pop music industrial complex and never regained any of that cachet. It’s disappointing, especially after reading the details in her 2021 memoir. It’s a tough read, but highly recommended if you’re into that kind of text.

2. “Vogue” by Madonna (1990)

After an unprecedented run in the 1980s that saw her rip off 16 consecutive (!) Top 5 singles on the Billboard Hot 100, it feels weird to say that “Vogue” came at a time when Madonna needed a hit, but that’s kind of how it started. At least her label thought so.

Her previous single, “Oh Father,” the last gasp from Like a Prayer‘s promotional cycle, peaked at No. 20. It was the first time Madonna had missed out on the Top in over a half-decade, which led Warner Bros. to commision a new song that could pump the tires on “Keep It Together,” which was the next release they had queued up for the Queen of Pop. Enter legendary DJ/producer Shep Pettibone, who had remixed some of her previous hits and recorded the bones of “Vogue” before Madonna wrote any of the words. The arrangement is minimal by today’s standards but intricately layered nonetheless: deep bass, handclaps, a simple keyboard hook, and a vocal performance that’s a rhythmic beast on its own. No wonder the label heads decided to put this one out as the A-side instead.

Admittedly, there’s a lot of co-opting of other (some might call them “cooler”) underground movements in “Vogue.” The bass line nods toward Detroit techno. The spoken-word bridge with all the Golden Age of Hollywood namedrops was Madonna’s first real acknowledgment of hip-hop. And then there’s the eponymous dance, which was supposedly “semi-passé” at the time of the song’s rise up the Hot 100. The voguing movement, created in Harlem’s Black and Latino LGBTQ+ ballroom community, straddled the finest of lines separating homage and appropriation, though it’s worth mentioning that historical analyses have been overwhelmingly positive in the latter regard. With this track’s commercial success, Madonna has been applauded for “helping build representation” for marginalized groups.

Here’s more from my review of I’m Breathless in my Madonna studio album ranking series:

“If recent sampling has taught us anything, this track is still incredible more than 30 years later. Everything about it, right down to the iconic music video, has aged like the finest of wine. […] Don’t forget to strike a pose while you listen.”

3. “Vision of Love” by Mariah Carey (1990)

I’ve covered Mariah Carey’s career extensively in this newsletter here, here, and here, so I’ll let you circle back to those articles for more context on just how dominant she was during the 1990s (60 non-consecutive weeks at No. 1 is but one of many mind-blowing stats). So many indelible pop classics to choose from, but rules are rules, and there can only be one. More than any other artist in this decade’s list, hers was the hardest single selection to finalize. “Fantasy,” “Dreamlover,” and “Always Be My Baby” were among the other contenders. But, in the end, you can’t talk about how Mariah redefined pop superstardom in the 90s without her immortal debut single, “Vision of Love.”

The moment this song hit the radio, every singer, experienced or aspiring, in America heard it and understood that the rules had changed forever. I’m sure many of you know the backstory, but it bears repeating that Carey was 19, co-writing her debut single with Ben Margulies over a gospel-influenced chord progression built around piano and light percussion. The production is restrained by early-90s pop standards, deliberately so, because it had to make room for the most important instrument to grace the Top 40 that decade: Mariah’s incomparable voice. Her use of melisma on this track didn’t invent the technique, but it certainly codified it as the soon-to-be dominant style in pop and R&B for the next two decades. Every American Idol audition, every Beyoncé run, every Christina Aguilera power note can all be traced back to what Carey did here.

Since this series is about No. 1 hits, it’s also worth sitting with the kind of pressure that was put on this particular 19-year-old’s shoulders to justify an entire label’s existence in pop music’s inner circle. Her ex-husband, Tommy Mottola, famously listened to her demo tape in a limo ride after a party and surmised, correctly, that she was a can’t-miss talent. Once-in-a-generation-type stuff. Her first decade in the industry bore that out, with her first four singles topping the Hot 100, including “Vision of Love,” which stayed in the top spot for four weeks. She became the first act since the Jackson 5 to achieve such dominance, laying the groundwork for one of the most celebrated runs in the history of recorded music, regardless of genre.

4. “Love Will Never Do (Without You)” by Janet Jackson (1991)

Speaking of incomparable runs, let’s give Janet Jackson her flowers for a minute. Specifically for Rhythm Nation 1814, which spawned seven singles, of which four went to No. 1 on the Hot 100. It made her the first artist to chart Top 5 singles from the same album in three consecutive calendar years and, for a little while, the most visible member, chart-wise, of the Jackson family. After all that momentum, “Love Will Never Do (Without You)” is a fitting final breath for the album’s hype cycle, allowing her to literally bask in the glow of that incredible sustained success. As an aside, I really miss this music video aesthetic. The high-contrast black-and-white mixed with the saturated, golden hues of the dreamiest beach setting, just glorious, y’all. The first person to successfully bottle and sell this aura will make a fortune.

Produced by Jimmy Jam and Terry Lewis, the song is (sort of) a departure from the harder-edged New Jack Swing sound that defined most of Rhythm Nation. The groove is lighter and more buoyant, with synth pads that are content to shimmer rather than punch you in the face like “Alright.” Janet’s vocals sit in a warmer, more relaxed register, too, a near-about-face from the militaristic precision of her performances on “Miss You Much” or the title track. In a way, it’s a successful test run for the softer, more sensual production Jam and Lewis would pursue with Janet on her self-titled album that would drop two years later. Everything about this song is aesthetically pleasing, partly because she makes it sound (and, in the video, look) so effortless. Queen-level stuff all around.

“Love Will Never Do (Without You)” marked a transition point between two incarnations of Janet Jackson. The message-driven artist of Rhythm Nation would soon give way to a more personally vulnerable artist who grappled with insecurities and missteps in love and life, as detailed through her music. The fact that both versions produced No. 1 singles tells you something about her range and her audience’s willingness to follow her anywhere she wanted to go. It’s worth quickly shouting some of those destinations out, in case you forget. There’s the slinky turn-on “That’s the Way Love Goes,” the house-fueled glow of “Together Again,“ and the rap-funk gem “Go Deep.”

All excellent, all completely different. All hail Janet.

5. “Black or White” by Michael Jackson (1991)

“Black and White” the lead single off Dangerous, his first album without Quincy Jones, and I don’t think you can overstate how much was riding on it. Sony had just handed him the biggest recording contract in history. He needed to prove he could function without Jones standing behind the boards, and he needed a hit that sounded like 1991 without abandoning the pop base that made him a phenomenon in the first place. Failure was not an option.

The result was pure spectacle. As I described in my original album review:

“At the time, demand for new MJ music was so overwhelming that this album’s lead single, “Black or White,” premiered simultaneously to an estimated audience of 500 million people in 27 different countries. In the U.S., it was broadcast live on MTV, VH1, BET, and FOX, giving those networks their highest-ever Nielsen ratings to that point. That level of control over the mainstream pop culture conversation had never happened before and will likely never happen again. Though Dangerous would initially outpace Thriller and Bad, selling 5 million copies worldwide in its first week, and eventually grossing over 32 million in sales, I’d argue the “Black and White” saturation levels are the more impressive commercial achievement.”

Suffice to say, huge is an understatement, but it shouldn’t be taken as an automatic. The song has a lot going for it, starting with that central earworm of a guitar riff recorded by Slash. It’s also a hugely entertaining example of organized chaos, stuffing in a (somewhat stilted) rap breakdown, paranoid undertones, undercut cries for racial unity, and the kind of vocal hooks that harken back to a pre-Wacko Jacko version of the pop star, when he was seen as reliably family-friendly. On top of all of that, the in-point to all the lyrical digressions is a man sidling up to Jackson’s girl that he took to a “Saturday bang.” You know, just minding his own business, thrusting his hips and grabbing his crotch in hyper-choreographed fashion.

How sincere you find the song’s message will, in large part, depend on how engaged you were with his persona back then and, relatedly, what your relationship with his legacy is currently. As a phrase, “it don’t matter if you’re black or white” landed at a moment when Jackson’s skin was visibly lighter and the public speculation about his changing appearance had become constant background noise. He attributed it to vitiligo, a diagnosis confirmed only after his death, but the rumors that he was turning his back on the Black community, even as his music was becoming audibly more “street,” was a massive sticking point for a lot of people.

As I said in that Dangerous review, there are no neutral parties when it comes to discussing Michael Jackson. None that I’ve met, anyway.

6. “End of the Road” by Boyz II Men (1992)

Beginning on August 18. In 1956, Elvis Presley’s “Don’t Be Cruel” / “Hound Dog” set a record for the most consecutive weeks at No. 1 on the Hot 100, with 11. Incredibly, that record survived 36 years of pop music challengers before, of all people, a vocal harmony group from Philadelphia finally toppled it with a ballad that Babyface wrote for an Eddie Murphy rom-com.

Still with me? That song was “End of the Road,” and the group was, of course, Boyz II Men, who held the top spot for 13 weeks, a record they’d break a couple of years later with their Mariah Carey collab, “One Sweet Day.” What gets me about this industry-shifting single is how you’d never in a million years pick this particular type of song or group to supplant Elvis effing Presley in the annals of Billboard chart history. There’s no rhythm track here, no top-of-mind sample doing any heavy lifting. It’s gimmick-free, letting those vocals carry the entire weight of the record. It was an unfashionable approach in 1992, and it seems even more unlikely today.

But Boyz II Men seemed destined for greatness at the outset. Serendipitously so. After forming in 1985, they got their big break, like a lightning bolt out of the sky, when they found themselves performing “Can You Stand the Rain” for none other than New Edition member Michael Bivins while he was backstage at a concert hosted by a Philly radio station. After some prodding, Bivins helped get the foursome signed to Motown and, in 1991, they dropped their debut album, Cooleyhighharmony. It was during a break in their tour schedule with MC Hammer that they recorded “End of the Road” with Babyface, who wrote and produced it with L.A. Reid and Daryl Simmons. The arrangement is pretty basic, leaving ample room for the stars of the show: those harmonies, which have more in common with doo-wop than anything else that charted that summer.

Boyz II Men’s heyday was relatively short. Their last No. 1 on the Hot 100, “4 Seasons Of Loneliness,” came in 1997, and their last Hot 100 chart entry was all the way back in 2000. However, they’ve made plenty of money on tour and with a wildly popular Las Vegas residency, where you’re pretty much guaranteed to hear this one to close out a show.

7. “I Will Always Love You” by Whitney Houston (1992)

“I Will Always Love You” and, to an even greater degree, the film whose soundtrack it was recorded for, The Bodyguard, is one of the unlikeliest of pop music smash hits in history. First, and most importantly, it wasn’t written for Whitney. Dolly Parton wrote and recorded the song first in 1973 and released it a year later. It’s a completely different beast from this version, taking a much softer, sunnier approach to the material. Its lyrics weren’t meant to be about romantic love, either. Parton intended this song as a tribute/farewell to her former business partner, Porter Wagoner, after she decided to break off and pursue a solo career. A few years later, Elvis wanted to cover it, but Parton turned him down after his management haggled with her over the publishing royalties. It all worked out for the best, as we’ll see.

Then there’s the Whitney Houston piece of all this. At first, she was reluctant to make the film, and then the studio wasn’t sure if she was still popular enough to anchor a romantic drama opposite Costner. During the recording sessions for the soundtrack, she wasn’t happy with the suggestion of the Motown standard “What Becomes of the Brokenhearted” as the film’s musical centerpiece, saying it was too much of a bummer to end the story on. And, even after they settled on “I Will Always Love You” as the song choice, it nearly sounded completely different. Whitney supposedly performed the first verse as an acapella to appease Costner, as it had been his idea to kick off “Brokenhearted” in order to slow down that song’s tempo. So, after all that, the single was released in early November 1992 and quickly became a phenomenon.

I don’t have to tell you it’s a brilliant bit of business from everyone involved, including David Foster, another music legend, who produced this, along with “I Have Nothing” and “Run to You,” for the soundtrack. You already know. It’s a maximalist marvel that shamelessly plays every moment to the back of the room and never, ever apologizes for it. Every element in the arrangement serves as a means to give its star the biggest, glitziest stage possible, and it succeeds on every level. The strategy paid off handsomely: the soundtrack quickly became one of the best-selling albums ever, with more than 45 million copies sold worldwide, and this single alone has sold over 24 million copies. It’s unquestionably Whitney’s career apex and also arguably Parton’s, as she’d earn $10 million in royalties in the 90s alone off this all-time classic.

8. “Weak” by SWV (1993)

Before Brian Alexander Morgan wrote what he called a “private little song,” “Weak,” for SWV, he was a Kansan who was discovered and signed to Warner Bros. by Club Nouveau’s Jay King in 1987. He moved to Sacramento, got free rein over the writing and recording of the debut LP for his group, Cachet de Vois, and then was promptly dropped by the label when that record tanked commercially. “I was hugely depressed,” he told Complex, “and also determined to not have to go back to Kansas. I started writing, and trying to get a solo deal for myself.” On top of all that, the real backstage tension at the heart of “Weak” was Morgan’s unrequited feelings for R&B mainstay Chanté Moore, who was seeing King at the time the lyrics were written.

Mrogan eventually found himself working with Martha Wash, who was coming off a landmark lawsuit against C+C Music Factory, at RCA, the same label that signed SWV (Sisters With Voices) earlier in the decade. Originally a gospel trio, Cheryl “Coko” Clemons, Tamara “Taj” Johnson, and Leanne “Lelee” Lyons were primed for a breakout of their own, and when Morgan first heard Clemons’ voice on a FedEx’d cassette demo, his reaction was immediate. “I heard Coko’s voice. And I was like, ‘Uh oh. This girl gonna be a problem,’” he said. The slow, warm groove exemplifies an aesthetic that would come to dominate 90s pop and urban radio: give your lead room to stretch and ache, and those feelings will translate into a raw, honest sonic gut punch.”

“Weak” topped the Billboard Hot 100 for two weeks in July 1993, knocking Janet Jackson’s “That’s the Way Love Goes” off the top after a two-month reign of its own. Along with several other R&B and hip-hop acts of the era, I’m encouraged by the fact that SWV is having a renaissance of sorts, despite this track being the only time they went to No. 1. They got close a couple of other times, most notably with the double A-side of “Right Here (Human Nature)” and “Downtown,” two other standout tracks from their glorious 1992 debut studio album, It’s About Time. Add that LP to your listening list if you’re not familiar, please and thank you.

9. “Gangsta’s Paradise” by Coolio feat. L.V. (1995)

Picture it: I’m a kid growing up in a mostly White suburb in Canada, and I hear “Gangsta’s Paradise” on the radio for the first time. The thundering kick drum blasts its way out of the itty-bitty speakers on the boom box I had at the time, followed by these equally outsized, menacing-sounding strings that, to me, would’ve been the music cue for a bad guy’s first appearance in an episode of a superhero cartoon. Then he starts rapping about walking through the valley of the shadow of death, and it blew my young, precious mind. Who was this? What exactly was this song? Was I even supposed to be hearing it? It was one of the first hip-hop tracks I fell in love with.

Back then, I had no concept of the arrangement’s Stevie Wonder connection (interpolating one of the most memorable moments from Songs in the Key of Life), religious overtones (that opening line borrows from and then diverges from Psalm 23:4), or the fact that it anchors one of the most perplexing “White Knight” movies of all time. Above all else, I was mesmerized by the unflinching nature of Coolio’s delivery, which is direct and measured, and the contrast between his bars and the levity of the sung choruses and the inclusion of the choir for even more heft. It’s also one of the last truly accessible rap songs that became such a monster chart hit. I hesitate to call it “family friendly,” but Coolio did clean up the profane language in his lyrics after Wonder initially refused to clear the sample.

Before his death in 2022 at the age of 59, Coolio had a winding, fascinatingly eclectic career in show business. He never got back to No. 1 on the Hot 100 (though his cover/update of Lakeside’s “Fantastic Voyage” peaked at No. 3), but managed to sell millions of records in the US and keep up a consistent touring schedule. He later starred in a reality TV show, Coolio’s Rules, authored a cookbook, and started an accompanying web series, Cookin’ with Coolio. He also had his fair share of legal issues, including being arrested for trying to get a loading firearm through LAX in 2016.

10. “Kiss from a Rose” by Seal (1995)

In 1996, my parents took my brother and me on a family road trip to Disney World. It was one of several Florida vacations I have vivid memories of, including (of course) which songs were in continuous rotation on local pop radio at any given moment. My mother recently corroborated my impression that, en route to Disney, I seldom passed up an opportunity to belt out Seal’s “Kiss From a Rose” whenever the day’s playlist circled back to it. How quickly that got on their nerves, I couldn’t say, but I imagine it would’ve been as ingratiating as actual seals singing the song. I was also obsessed with Batman Forever because of the toys and merch, particularly action figures like this. Simpler, more exciting times.

Back to the song. Seal wrote it all the way back in 1986 or 1987, living in a squat in London with no money and no studio access. The orchestral arrangement he was hearing in his head wasn’t something he could afford, so he layered 16 or 17 vocal tracks on a 4-track machine to simulate a similar effect. By the time producer Trevor Horn finished producing the final version eight years later, those stacked vocals had become strings, choir, and what Horn himself called a record that “didn’t easily slot into any genre.” The melody is baroque, almost medieval, and the chord progression keeps moving in directions you don’t expect. The whole affair still doesn’t have a fixed address in pop history. It doesn’t sound like 1995. It barely sounds like 90s pop music at all.

When it appeared on Seal’s second album in 1994, it entered the UK charts around No. 60 and disappeared a couple of weeks later. The crooner thought it was “dead” until it was included on the aforementioned movie’s soundtrack in 1995. The summer blockbuster was a massive hit, and the association drove the track’s chart run, culminating in a peak at No. 1 in August. Improbably, “Kiss From a Rose” nabbed three Grammys at the next ceremony, including Record of the Year and Song of the Year. Seal’s take on the whole arc is the only framing it needs: “It was always a great record. The only difference is that people got to hear it.”

11. “This Is How We Do It” by Montell Jordan (1995)

Sometimes, there’s no need to over-intellectualize pop hits.

Not every great No. 1 song needs to be emotionally complex or thematically challenging. More often than some music snobs would be willing to admit, less is more. Simpler is better. Some records transcend time and space based on their vibes alone, and one of those classics is Montell Jordan’s “This is How We Do It.” As soon as the sung opening statement wafts through your headphones or speakers, you’re instantly reminded that Friday night, wherever you are, is the only place worth being, full stop. Because of how straightforward it is, I’d argue that, more than any song on this list, this one would have the best chance at getting back to No. 1 today.

Built around a sample of Slick Rick’s “Children’s Story” from 1988, the production fuses that backbone with a bass-heavy, uptempo R&B groove that owes equal debts to New Jack Swing and West Coast G-funk. It was one of the final times either aesthetic appeared in the beat of a No. 1 single from the 1990s, too. As a vocalist, Jordan sounds completely relaxed the whole way through, never straining for an inflection or “moment” he doesn’t need to force. The hook itself, “this is how we do it,” is about as economical as attention-grabbers get. He was 26 and making his debut, and this record became the record that defined his entire career, spending seven weeks at No. 1 after knocking Madonna’s “Take a Bow” off that pedestal

Jordan never quite matched that commercial success after that nearly two-month run atop the Hot 100. He had some follow-up heat, “Get It On Tonite,” which reached No. 4 in 1999, and he wrote and produced memorable cuts for other artists, including Deborah Cox’s “Nobody’s Supposed to Be Here” and Sisqó’s “Incomplete.” He left Def Jam in 2003, spent a few years chasing an indie comeback that never materialized, and then, during a church fast in 2010, he says God told him to quit music entirely. He decided to dedicate his life to his faith, leading to him and his wife Kristin later co-founding their own virtual church and a couples’ ministry built around their own experience surviving infidelity and bankruptcy.

He still gets plenty of nostalgia-maxing mileage out of this track, though.

12. “Waterfalls” by TLC (1995)

“Waterfalls” was a moment for TLC. A triumph, to be sure, earning its mettle as the most socially conscious No. 1 record of the decade, but also as a cautionary tale. This song was the group’s second of four Hot 100 chart-toppers, with the first being 1994’s “Creep,” and it also enjoyed a ton of international success, topping several other singles charts on the other side of the Atlantic. However, in July of 1995, while “Waterfalls” sat at No. 1 in the US, the trio filed for bankruptcy, citing the “greedy people” managing their careers behind the scenes as the main reason they were broke. You hear a lot of (mostly accurate) rants about how it’s impossible for musicians to make money these days, but it wasn’t much different 30-plus years ago. Despite being one of the biggest acts on the planet, each member was taking home less than $35,000 a year after everyone else got their cut. Make it make sense.

Organized Noize (Sleepy Brown, the late Rico Wade, and Ray Murray, the Atlanta crew that built the sonic foundation of the Dungeon Family) produced this record, crafting an arrangement that’s fluid and spacious in a way that only Southern-leaning hip-hop and R&B can execute. T-Boz’s lead vocal sits in a lower, more conversational register, providing this grounded storytelling anchor while Chilli’s harmonies float in and out around her. Left Eye’s rap coda, a 45-second meditation on faith and living one’s life with empathy, functions almost like a Greek chorus, offering what is, on paper, a much-needed silver lining of hope to an otherwise bleak portrait. TLC had to fight to release it as a single at all. As T-Boz later told it, “ He [Clive Davis] said it was too deep. He didn’t think people would bump up the street to it.” They went over his head straight and got the budget for both the single and the million-dollar video anyway.

Then there’s the socially conscious aspect I mentioned earlier. “Waterfalls” is widely cited as the first No. 1 single in the US to directly reference AIDS, which was unheard of in 1995 in terms of mainstream pop radio content. That said, you could easily blink and miss it if you’re not looking for it, which is part of the track’s power. It handles drug dealing and HIV without descending to preachiness or manipulative martyrdom. Instead, it distills the weighty topic into a straightforward image of beauty and resilience. Left Eye opens her verse with, “I seen a rainbow yesterday,” a detail Chilli later said came from something that actually happened the day before they recorded it. The song, which spent seven weeks at No. 1 and won TLC four MTV VMAs, including Video of the Year, helped propel their album CrazySexyCool to Diamond status. At the time, it was the first LP by a girl group to earn that distinction.

13. “How Do U Want It” by 2Pac feat. K-Ci & JoJo (1996)

Okay, I’ll admit, this selection’s a bit of a cheat.

The only reason that “How Do U Want It,” one of the best tracks on 2Pac’s legendary double LP, All Eyez On Me, went to No. 1 at all is thanks to “California Love.” The latter had dominated Top 40 radio since December 1995, but Billboard required a commercial physical single before any song could chart on the Hot 100, and Death Row Records didn’t follow through with one until June 1996. When that finally happened, the label bundled “California Love” with “How Do U Want It” and Billboard counted both songs together. This trick wasn’t new to record labels or artists. Elvis did it with “Hound Dog” and “Don’t Be Cruel” in 1956. The Beatles did it four times in the UK. By the mid-90s, it was a refined but shameless tactic that threw a small but meaningful asterisk onto Pac’s only Billboard Hot 100 No. 1.

So why this track and not “California Love?” Because “How Do U Want It” shows a side of Pac that the louder, more combative gangsta rap entries in his catalog tend to crowd out. The production does a ton of work to bring that aspect of his persona to the forefront, too. Johnny J built the track on a sample from Leon Ware and Quincy Jones’ “Body Heat,” a slow-burning 1974 soul record that oozes effortless cool. That sample reads as a direct line of succession, bridging the ethos of Black pop culture excellence from the mid-70s to 1996. The K-Ci and JoJo’s hook, pure Jodeci-school silk, reinforces that continuity. Nothing about this record is hard or paranoid like the rest of the album. It’s luxuriant, Pac letting the groove carry him rather than bending the track to his anger or disgust. That version of him, unhurried and in full control, is the one the public got the least of.

Less than two months after the single topped the chart, he was shot four times in the passenger seat of Suge Knight’s BMW on Flamingo Road in Las Vegas, leaving a Mike Tyson fight. He died six days later at 25, and nobody has been charged for it in the nearly three decades since. The case remains one of the most famous unsolved murders in American history, though a suspect was arrested on suspicion of committing the murder in 2023. The man, Duane Davis, has pled not guilty to the charges and, as of this writing, is awaiting his day in court. What makes “How Do U Want It” linger is the way the song conveys what he was likely capable of as a maturing artist. All that ease, all that warmth, all that room to breathe, and the endless speculation, both internally and in conversation with friends, of what he could’ve accomplished had he not been taken from us at such a young age.

14. “You’re Makin’ Me High” by Toni Braxton (1996)

Before writing this list of my favorite Billboard No. 1s of the 1990s, I didn’t realize how much of a direct sequel to “Waterfalls” Toni Braxton’s “You’re Makin’ Me High” was. The more I read, the more eye-watering the numbers and fallout became.

This song was a good example of LaFace and Arista playing both sides of the mainstream radio aisle simultaneously. “You’re Makin’ Me High” was another double A-side release, this time coupled with the adult contemporary cut “Let It Flow,” one of several memorable moments off the Babyface-produced Waiting to Exhale soundtrack. It turned the release and Braxton’s accompanying studio album, Secrets, into a runaway commercial freight train, with the latter going on to sell 15 million copies worldwide. Grammy wins followed for Best Female R&B Vocal Performance for this record, as well as Best Female Pop Vocal Performance for “Un-Break My Heart.” Sadly, what didn’t follow was a payout that matched the size of this particular success story.

Combined, Braxton’s debut album and Secrets generated an estimated $170 to $188 million in revenue for Arista and LaFace. Her royalty payout between both albums? A touch under $2,000. Braxton filed for Chapter 7 bankruptcy in January 1998 and later confirmed that LaFace had gagged her from speaking publicly about the situation while TLC’s story was still playing out in the press. “People don’t understand that this issue went all the way to Congress,” she said later, referring to California Labor Code Section 2855, referred to as the “Seven Year Rule,” which limits personal service contracts to seven years for all California workers. In 1987, the RIAA successfully lobbied the state legislature to carve recording artists out of that protection, and the fight to claw back those rights has been raging ever since. The major labels killed a 2001 effort to reverse this decision, and both the FAIR Act and AB 983, which surfaced in 2021 and 2022, respectively, have stalled.

Between “You’re Makin’ Me High” and “Un-Break My Heart,” Braxton spent a total of 83 weeks on the Hot 100, and it’s easy to hear why in either case. Her low contralto carries the weight of lust and heartbreak with equal mastery, balancing the perceived classiness that you needed to chart as an adult contemporary act with the simmering sex appeal that meant you could pair her with more uptempo, club-friendly instrumentals. Of all her hits, “You’re Makin’ Me High” showcases that voice at its most entrancing. She’s not belting out lyrics from the diva ballad mountaintop, but instead is willing to get down and dirty (literally) with the common folk. We should be so lucky/

15. “Hypnotize” by The Notorious B.I.G. (1997)

By the time “Hypnotize” rose to claim the top spot on the Hot 100, the Notorious B.I.G., one of the greatest talents to emerge from hip-hop’s golden age, was already dead.

The tragic timeline is, roughly, this: Bad Boy and Arista released this track as the first radio single from the Notorious B.I.G.’s forthcoming second album, Life After Death, on March 4, 1997. On March 5, he gave a radio interview in San Francisco to promote the song and, during the conversation, said he’d hired security because he feared for his safety. On March 9, en route to an after-party to celebrate the LP’s upcoming release, a shooter fired six bullets into the Suburban the rapper was riding, four of which hit him. He was pronounced dead a little over a half-hour later at age 24. Once the physical single became available in late April 1997, it debuted at No. 2 (the second-ever track to do so) before going to No. 1 the following week.

The consummate rap party anthem is built around another No. 1 hit from 1979, Herb Alpert’s “Rise.” When Sean “Puffy” Combs first played the loop for Biggie, the story goes that he just smiled and hugged the producer. The Alpert sample apparently spoke to the emcee as a kid who grew up in New York during that era, when the Alpert track and Chic’s “Good Times” were ”the songs that all the kids were dancing and roller skating to that summer.” The sample gives “Hypnotize” this expansive quality, all brass and shimmer, basically a red carpet rolled out for Biggie’s verses, which roll off the tongue with such style and charisma, you can’t picture anyone else firing off those bars. The chorus, delivered in uncredited fashion by Pamela Long, interpolates Slick Rick’s phrasing from “La Di Da Di,” threading yet another historical item into this track’s DNA.

This song made Biggie the fifth artist in Hot 100 history to top the chart posthumously and the first since John Lennon had last done so in 1980 with “(Just Like) Starting Over.” Life After Death, his masterpiece of a double album, debuted at No. 1 on the Billboard 200 and sold a massive 690,000 copies in its first week. This ode to “Hypnotize,” alongside the 2Pac entry a few spots up, forms a kind of paired reckoning. Two artists, both killed within six months of each other, both topping the Hot 100 under circumstances overshadowed by violence brought on by the senseless East Coast-West Coast rap beef. But this song in particular lives on precisely because it doesn’t wallow in paranoia. It’s about triumph, excess, and the sheer joy of being the best rapper alive.

16. “All My Life” by K-Ci & JoJo (1998)

Up until 1996, brothers Cedric “K-Ci” Hailey and Joel “JoJo” Hailey made up half of the R&B group Jodeci, who, despite their rampant popularity in North America, never had that one massive single that put them over the top like Boyz II Men did. The closest they got to a Hot 100 No. 1 single was with “Lately,” which peaked at No. 4 in 1993. Other well-known tracks, like “Come & Talk to Me” and “Freek’n You,” failed to crack the Top 10. After the group announced a hiatus in 1996, K-Ci and JoJo split off into a separate duo and promptly delivered one of the most sumptuous and memorable ballads of the decade, “All My Life.

The year of this success story is notable, too. By 1998, those big, sweeping love songs had, for a little while anyway, run their course. Hip-hop and R&B audiences alike showed an increasing appetite for stranger, more experimental concoctions from the likes of Timbaland (see his early work with Missy Elliott and Ginuwine), Darkchild, and several others. Instead of trying to bridge that newly noticeable gap, the Jodeci alums ran in the opposite direction, leaning into what you’d call a more “traditional” sound today. The arrangement is deliberately spare, using primarily piano, percussion, and two towering voices to do all the heavy lifting. The latter aspect is the reason this track has any staying power to begin with, and I do mean “power” in the fullest sense of the word. There’s a raw intensity to K-Ci’s gospel-inspired tenor, particularly in that bridge and breakdown before the final chorus, that you can’t fake. You just close your eyes and welcome it into your soul.

The Hailey brothers had a good run of it to close out the 1990s. In addition to “All My Life” and the cameo on 2Pac’s “How Do U Want It,” they almost nabbed a third Hot 100 No. 1 in 1999 with “Tell Me It’s Real.” They’ve released several studio albums since then, with varying levels of commercial success, the last of which, as of this writing, came in 2013. Their working relationship has seen its fair share of turbulence, as seen in the docuseries K-Ci & JoJo... Come Clean, which peeled the curtain back on, among other things, both men’s struggles with substance abuse. This single was undeniably their peak and, with those harmonies in their collective arsenal, it’s easy to see why they became as popular as they did outside of Jodeci.

17. “The Boy Is Mine” by Brandy & Monica (1998)

The biggest-selling single of 1998, moving over 2.5 million copies, “The Boy is Mine” gives us an excuse to discuss three of my favorite artists from the 90s: singers Brandy and Monica, and producer Rodney Jerkins, who’s better known by his stage name, Darkchild.

Let’s start with Jerkins. The New Jersey native came from a musical family (his father and brother played piano at church gatherings) and was so hell-bent on starting his own empire that he turned down several golden opportunities to enter the music industry while still a teenager. He said no to a contract at his mentor Teddy Riley’s label, as well as Bad Boy Records, while he was still a teenager. After inking a worldwide publishing deal with EMI before he turned 18, Jerkins has said that his first big projects were working on records for Mary J. Blige, Whitney Houston, and the two women you hear on “The Boy is Mine.” Not a bad way to start an enormously high-profile producing career.

As teen pop stars, Brandy Norwood and Monica Arnold were cut from a similar cloth professionally. They rose to prominence around the same time (Brandy dropped her studio debut in 1994, Monica in 1995), translated singing success into plenty of acting gigs, and, for this song, they each added a Grammy to their trophy case. But initially, their labels didn’t want them to partner on a duet, much less one about a soured love triangle, fearing that it would add fuel to the public speculation that they were rivals nipping at each other’s heels within R&B singles. The two insisted that wasn’t the case and, though it’s been frequently cited as an update of Michael Jackson and Paul McCartney’s “The Girl is Mine,” Jerkins has denied that in interviews, adding that the similarities only dawned on him and everyone else involved with the project after recording was completed.

And, let’s be honest, it’s a much better song across the board. Jerkins’ harp-like synth riff is one of several beguiling hooks that dot his early production discography, floating high above the rippling bass-and-drum foundation underneath. The vocal performances, which were re-recorded after an initial joint session where both women sang in the same room, are expertly calibrated to play off each other. Despite reports that the pair didn’t get along, they nonetheless won a Grammy for Best R&B Performance by a Duo or Group with Vocals for this track, which has become the all-time #1 female duet in US chart history. There’s even a happy ending to this story: The duo reunited in 2012 for “It All Belongs to Me,” a tribute to Whitney Houston.

18. “Doo Wop (That Thing)” by Lauryn Hill (1998)

While she hasn’t been the most prolific artist in the world, few female voices across R&B and hip-hop have left the kind of generational impact that Lauryn Hill’s has.

Beyond her outstanding work as a member of the Fugees (their 1996 album, The Score, featuring their cover of “Killing Me Softly,” has sold over 22 million copies to date), her crowning achievement has to be 1998’s The Miseducation of Lauryn Hill, which won five Grammy awards including Album of the Year, making it the first hip-hop album ever to take home that prize. The LP’s lead single, “Doo Wop (That Thing),” also broke numerous Hot 100 chart records, including becoming the first hip-hop song by a soloist to debut at No. 1 and the first debut single in any genre to do so. Perhaps most impressive of all, Hill was only 23 years old when she became, somewhat overnight, the biggest name in pop music.

She produced this track herself, building it around piano chords and a horn arrangement that deliberately reaches way back to 1960s soul. But she raps as much as she sings here, sliding between registers with this incredible innate fluency. I’d go so far as to say no one on this list holds a candle to that level of relatable, natural flow behind the mic. Lyrically, she’s warning women and men alike against “that thing,” a phrase she keeps elastic on purpose so it can stand in for references to everything from sexual recklessness, materialism, and emotional self-destruction all at once. It’s all about your perspective. The key to pulling that kind of conceit off as well as she does is tone, which comes across as more exasperated than righteous or preachy. The split-screen video, set simultaneously in 1967 and 1998, makes the visual argument explicit.

In a way, the larger point of “Doo Wop (That Thing)” might be that none of what she’s addressing is new. It’s generational, to a degree foreseeable, and it all just keeps repeating year after year, decade after decade. The album as a whole traffics in this grey area of human nature as it relates to relationships. Hill was pregnant with her second child for most of the Miseducation sessions, which surely helped sharpen a lot of those themes. The fact that her exceptional run in 1998 and in 1999 resulted in her name being etched in the history books as the first Black woman to win Album of the Year since the category began tells you that, sometimes, the Academy gets it right.

19. “Bills, Bills, Bills” by Destiny’s Child (1999)

Let’s move from one Black female music icon to another and discuss Beyoncé’s first No. 1 as a member of Destiny’s Child with their empowerment earworm, “Bills, Bills, Bills.” When this song topped the Hot 100, Ms. Knowles was all of 17 years old, and none of her groupmates were over 18. Bey wrote the lyrics for this track with LeToya Luckett, LaTavia Roberson, Kelly Rowland, and Kandi Burruss, while production was handled by She’kspere (Kevin Briggs). The instrumental is this off-kilter brand of uptempo, serving up a rhythmically choppy, guitar-driven groove that sits right at the intersection of R&B and pop. It’s an odd bird, but it works so, so well.

It’s worth lingering on Beyoncé’s lead vocal for a moment, since I think it foreshadows much of what would become her calling card in the 2000s, both as a member of Destiny’s Child and as a solo act. In between the harmonies, she comes in with a sharpness and authority that’s unusual for a teenager, never mind someone with much more performance experience under their belt. The songwriting, which is essentially an itemized financial complaint on the surface, plays as a precursor to a single like “Irreplaceable,” which would drop less than a decade later. The same matter-of-fact receipt-airing (literally, in this case) has evolved into an inextricable part of her persona. I know my worth in this relationship, and if you can’t handle it, there’s the door.

Destiny’s Child was still a four-piece at the time of recording, before Luckett and Roberson were replaced by Michelle Williams and Farrah Franklin in early 2000. “Bills, Bills, Bills” was taped during the same Writing’s on the Wall sessions that also produced hits like “Say My Name,” which, buoyed by Jerkins’ production, carries more than a hint of Brandy and Monica’s sensibility. But this girl group operated in a different emotional register from the glut of others who saw widespread chart success in the 90s—impatient, specific, and fully unapologetic. It’s one of several reasons why the group’s music has stood the test of time.

20 “...Baby One More Time” by Britney Spears (1999)

Time to end this list off on a high note with a couple of important Hot 100 origin stories: Britney Spears and Max Martin.

Let’s start with the lesser-heralded of the two in Martin, who had been knocking on the door of Hot 100 greatness for four years before this song finally kicked it in. Born Karl Martin Sandberg in Stockholm, he’d cut his teeth in the business in Sweden as a house writer at Cheiron Studios starting in 1992. His first Hot 100 entry came in October 1995, when the Backstreet Boys’ “We’ve Got It Goin’ On” entered at No. 97. Another BSB single, “Quit Playing Games (With My Heart),” got him up as high as No. 2 in 1997. He co-wrote Robyn’s “Do You Know (What It Takes)” and watched it land in the top 10 the same week. Then, after TLC turned down this song (what a sliding doors moment that is), Simon Cowell tried to buy it for his boyband Five, reportedly offering Martin a Mercedes-Benz as a sweetener. Martin declined both times.

Instead, his mentor, Denniz PoP, died of cancer in the summer of 1998, leaving Martin to take over the studio with a new primary partner, Rami Yacoub. The duo hitched their prospects to a 16-year-old Jive Records signee who was about to pop off in a big way. Many of you may be familiar, at least in passing, with Britney’s backstory: a Louisiana native who was a former Mickey Mouse Club cast member, alongside names like (eventual ex) Justin Timberlake and Christina Aguilera, before any of them had a record deal. According to Nigel Dick, the music video’s director, the entire concept of a high school hallway, Catholic schoolgirl uniforms, pigtails, etc., was the singer’s idea. She even contributed choreography. She was 16 and already directing her own image with complete authority. How global her reach as a pop superstar became later on should come as no surprise, given those anecdotes.

The rest, as they say, is history. “Baby One More Time” and Britney’s eponymous debut studio album both hit No. 1 on the Hot 100 and the Billboard 200 in the same week. The album eventually sold 14 million copies in the US alone, making it the best-selling album of 1999, and the single moved over 10 million units worldwide, also vaulting it into rarified air for physical single releases. It was Martin’s first No. 1 as a writer and producer, a distinction he’s earned an additional 28 times, breaking Paul McCartney’s all-time record in 2024. Rolling Stone named it the greatest debut single of all time in 2020, and the TLC rejection remains an apt throughline to close the decade, prefacing a new era of the Hot 100 that would belong to international songwriters and various types of polished craftmanship that opened a multitude of new doors for artists and listeners alike.

Which No. 1 from the 90s still hits hardest for you? And which one did I miss? Drop it in the comments.

My 100 Favorite Recordings from the 1990s

The 1980s Billboard Hot 100 chart archive is one of the most entertaining documents in American pop culture history.

This weekly survey crowned Prince, Michael Jackson, and Madonna as some of music’s biggest tastemakers, but also left plenty of space for Falco singing in German about Mozart, Bobby McFerrin doing an entire song a cappella without a single instrument, and a Norwegian band whose video was a rotoscoped pencil-sketch animation. In the same ten-year stretch, Toni Basil would get to No. 1 for one week, while Olivia Newton-John stayed there for 10.

MTV loomed large, syndicated countdown shows democratized pop music’s national reach, and new subgenres and movements emerged as commercial titans (see synth-pop, hip-hop, and thrash metal). The No. 1s of the 1980s are an embarrassment of riches (and, in a couple of cases, pure embarrassments, though those tracks won’t make it onto this list) that, by and large, have stood the test of time. “80s Gold” is still the most bankable radio format in North America.

It was also the last decade that relied on Billboard’s old (some might say “corruptible”) methods for determining which songs were worthy of chart inclusion. Beginning in 1991, Nielsen SoundScan data became the standard, instead of self-reported record store sales numbers. That meant a consolidated pool of artists who would ultimately stay at the top of the Hot 100 for longer periods.

As with every other installment in this Billboard Hot 100 series, this isn’t your standard “best of the 80s” list. It’s a collection of 20 songs that have left the greatest impression on me as a music nerd, and also happened to hit No. 1 between 1980 and 1989. I only allow myself one song per artist, so there’s only a single track from Madonna on this list, for example.

Plenty of great 80s songs couldn’t have possibly made this list because they never topped the chart. Those include:

• “Thriller” by Michael Jackson, which peaked at No. 4

• “Purple Rain” by Prince, which topped out at No. 2

• “Tainted Love” by Soft Cell, which stalled at No. 8

If you’re new here, the 1960s and 1970s lists are already up. Paid subscribers also get the companion playlist for each decade (one-song-per-artist rule there, too). Skip to the playlist and/or upgrade your subscription tier if you’re down for bonus content you can listen to.

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We begin, in chronological order:

1. “Crazy Little Thing Called Love” by Queen (1980)

I wrote about Queen’s path to get to “Crazy Little Thing Called Love,” their first American No. 1 single, early in 2026, so I won’t go into as much detail here. But, suffice it to say, the band was in need of a commercial breakthrough. Mercury and company dialed back the theatrics quite a bit on this track and throughout The Game, the ensuing LP that, for a short period, put them back on top of the pop-rock world. A not-insignificant part of this record’s appeal is how uncomplicated it is. Unlike “Bohemian Rhapsody” and other, more grandiose tracks of its ilk, this song is as straightforwardly fun as they come, and that energy is infectious from the first note.

The story goes that Mercury wrote “Crazy Little Thing Called Love” in roughly ten minutes while sitting in a bathtub at the Bayerischer Hof hotel in Munich. He also played acoustic guitar on the recording, one of the few times he contributed to a Queen session as a guitarist. The rhythm is obviously reminiscent of Elvis Presley and other 50s rock and roll greats, with a walking bass line and a percussion swing that hums with this warm, wistful confidence. Brian May also switched things up on this record, playing his solo on a Fender Telecaster rather than his homemade Red Special, deliberately aiming for a vintage tone.

The result is production that’s quite lean and dry compared to Queen’s trademark layered excess, and that restraint is (more or less) the point. “Another One Bites the Dust,” another No. 1 smash off the same album, takes the same tack with a disco-funk stomper that ingratiated the band to R&B (then dubbed Black) radio. A maximalist band scoring a generational hit with a minimalist arrangement. It can be done.

2. “Bette Davis Eyes” by Kim Carnes (1981)

Sometimes I keep going back to songs for the tone and texture of certain sounds. Not necessarily instruments that repeat across multiple entries on a tracklist, but a specific aural pleasure that always hits your neural pleasure centers in exactly the right way. One of those sounds is the main synth on Kim Carnes’ “Bette Davis Eyes,” which spent nine non-consecutive weeks atop the Billboard Hot 100 in 1981. You can thank keyboardist Bill Cuomo for that riff, which he played on the Prophet-5 synthesizer, for creating chords that give me chills every time I hear them.

That instrumental hook was also what got the song made in the first place. The lyrics were originally penned by Donna Weiss and Jackie DeShannon in 1974, with the latter recording the demo herself as a country-leaning pop ballad. Carnes and producer Val Garay circled it for a little while, as did other artists, before Carnes ultimately rejected it based on the demo’s arrangement. But after they started rebuilding the song’s structure from scratch, it quickly took shape. Cuomo’s playing replaced acoustic guitars, the drums became drier and punchier, and Carnes’ husky vocal sits between rock and new wave.

It’s kind of shocking that Carnes, with all the ability and charisma displayed on this track, never became more of a household name. She had been working as a singer-songwriter since the late 1960s, and was respected in Nashville and Los Angeles circles without ever “making it.” She’s one of the decade’s defining one-moment artists, a term I’m coming to prefer over the dismissive nature of calling someone a one-hit wonder. In addition to being the longest-running chart-topper of 1981, “Bette Davis Eyes” won Grammy Awards for Record of the Year and Song of the Year.

Davis herself reportedly sent Carnes and the songwriters a thank-you note regarding its lyrical portrayal of a certain brand of female knowingness (if you know, you know).

3. “9 to 5” by Dolly Parton (1981)

Before she was cast in 9 to 5, Dolly Parton was already a music star, albeit a niche one. Well known in country circles, but not much of a pop chart presence, save for one Top 5 single with “Here You Come Again.” That all changed in 1980, when Parton starred alongside Lily Tomlin and Jane Fonda as three office workers who kidnap their sexist, scummy boss (Dabney Coleman) and, what do you know, improve the quality of life of all employees in the process. It ended up being the second-biggest domestic film from that year—only The Empire Strikes Back made more money at the box office. That cultural cache made Parton a different level of superstar.

In that moment, it’s not a surprise that the film’s eponymous theme song went to No. 1. It’s more bubbly, catchy, and charming than almost everything else in Parton’s catalog, which is saying something. Parton’s phrasing and performance do most of the heavy lifting here, turning what could have been a forgettable novelty tie-in into a pop cut with personality to spare. She also came up with the rhythm by clicking her acrylic nails together (you can hear them getting the groove started at the very beginning of the track). Once that walking bass line comes in, all bets are off. Your defenses are officially broken down.

Though it alienated some purists in her base, Parton’s crossover success set the template other hopefuls would replicate in the decades that followed: country enough that it still had ties to her roots, but pop enough to dominate the Top 40. And dominate it did, reaching No. 1 for two weeks on the Hot 100 and simultaneously topping the country chart. The song also received an Academy Award nomination for Best Original Song, ultimately losing to “Fame” by Irene Cara. Whether or not you agree with that Oscar decision, the run-off was undeniable. Parton was, suddenly, one of the biggest American entertainers in the world.

4. “I Can’t Go for That (No Can Do)” by Hall & Oates (1982)

Let me tell you all something right now: There is no pop song on planet Earth—not now, not ever—with a groove as locked in as Hall & Oates’ “I Can’t Go for That (No Can Do).” The first time I heard it almost 25 years ago, I couldn’t get over how cool it sounded. Effortlessly so. The drum machine pattern, created using a Roland CR-78 CompuRhythm, was mic’d through the bass amp with delay, giving it an otherworldly strut. Daryl Hall played the bass portion on a Moog synthesizer in such an unhurried fashion that the beat doesn’t need to do much else to persuade you.

Hall grew up in Philadelphia, steeped in Gamble and Huff’s sound, and his understanding of R&B wasn’t borrowed or plasticized (despite what the “blue-eyed soul” connotation would have you believe). It comes off as a deep cut more than a hit on first blush, with an instrumental that would fit right in on late-night soul broadcasts. Hall’s vocal is more standoffish than inviting, more preoccupied with boundary-setting than whatever physical pursuits might come after those have been established. It’s a weird, sparse, and utterly transfixing song.

Michael Jackson reportedly told Hall that “I Can’t Go for That” was a direct influence on “Billie Jean.” There’s been some debate as to whether that’s 100% true or not, but if accurate, it makes this track the ghost in the machine of one of the biggest pop singles of all time. In 1982, Hall & Oates were in the most commercially dominant stretch of their career, charting six No. 1 hits between 1980 and 1985. Of those, “I Can’t Go for That” is the one that matters most to people across all genres. It held No. 1 for one week on the Hot 100 and topped the R&B chart at the same time, emerging as one of several successes off the multi-Platinum Private Eyes LP.

5. “Don’t You Want Me” by The Human League (1982)

I don’t think you can call the Human League’s “Don’t You Want Me” the first true synth-pop song, but it was the first of its kind to take over the Hot 100, spawning a zillion imitators in the process. However, at first, Phil Oakey didn’t even want to release the track as a single. He thought it was too conventional a pop song to warrant a ton of consideration, but Virgin Records insisted. Sometimes, the suits are right, as this release has become the group’s biggest wide by a wide margin in the US.

In what will become a bit of a trend as we move on down the list, the real trick synth-pop pulls when it’s this well done is wringing a ton of drama out of stripped-down production. Martin Rushent’s work here is built almost entirely on synthesizers and a LinnDrum machine, but even then, it never sounds small or insignificant. The call-and-response structure between Oakey and Susan Ann Sulley also gives the song a nice bit of narrative tension that most of those imitators lacked. Sulley and Joanne Catherall were relatively fresh members at the time, recruited out of a Sheffield nightclub to strengthen the group after earlier members departed to form Heaven 17.

The track held No. 1 for three weeks on the Hot 100 and five weeks in the UK. Parent album Dare went Platinum on both sides of the Atlantic, too, proving that synth-pop had much broader appeal outside Britain. After this one hit, the floodgates opened for real, providing runways to US pop stardom for acts like Depeche Mode, Soft Cell, Duran Duran, and Eurythmics. The Human League are far more than just this one hit as well. If you dive deeper into only one catalog cited in this list, I urge you to consider theirs. There’s a ton of exceptional material to explore.

6. “I Love Rock ‘n’ Roll” by Joan Jett and the Blackhearts (1982)

23, folks. That’s how many record labels passed on Joan Jett before she self-released “I Love Rock ‘n’ Roll” on Boardwalk Records. It’s not like she was a complete unknown or anything. She had already been in the Runaways, the all-female hard rock group that broke up in 1979 after four albums, plenty of international touring, and even more memorable on-stage antics. And yet, for whatever (misogynist) reason, the industry looked at her track record and said “no” that many times. The song eventually spent seven weeks at No. 1 on the Hot 100 in 1982.

“I Love Rock ‘n’ Roll” was also the first in a long line of successful covers that would solidify Jett and her band as a force to be reckoned with. The Arrows, a British glam-rock band, originally recorded this one in 1975, but it received only a whisper of a commercial response. However, Jett heard it during a UK tour with the Runaways and soon after began performing it live. When she had a band and a label willing to release it, she and producer Kenny Laguna built the studio version around a Chuck Berry-influenced guitar riff, supporting by power chords, stomp-clap drums, and a snarling vocal that makes the title sound like a claim rather than a preference.

Despite earning the title of “Godmother of Punk,” Jett’s prowess as a performer has mostly flown under the radar. After this effort, she’d only crack the Top 10 on the Hot 100 twice more—later in 1982, with another cover, this time a terrific version of “Crimson and Clover,” and again in 1988 with “I Hate Myself For Loving You.” The latter also earned her a Grammy nomination for Best Rock Performance. It’s a shame she didn’t have another “I Love Rock ‘n’ Roll” in her career.

7. “Billie Jean” by Michael Jackson (1983)

Michael Jackson’s “Billie Jean” is, above all else, proof positive that less is more.

A lesser, more convoluted version of this song would have far more (and far less necessary) sonic pyrotechnics going on. Instead, you’ve got a handful of notes that add up to an iconic bass line, played by Louis Johnson, and a sturdy, straightforward drum groove supplied by Leon “Ndugu” Chancler. But those aspects were also painstakingly constructed by Quincy Jones and engineer Bruce Swedien, who supposedly put plywood on the floor to get the low-end to thump just the way they wanted. All of Thriller has a remarkable attention to detail, but this song in particular impresses in that regard.

Even more incredibly, “Billie Jean,” one of the most beloved dancefloor anthems of all time, is a tight knot of paranoia and denial. The lyrics, which may or may not have been inspired by true events, position Jackson as either a wrongfully accused man terrified of what false baby daddy claims will do to his image, or a panicked lothario who’s overcome by something approaching (but not quite registering as) guilt. When the synths arrive in the mix before the first verse, they do so with unease rather than warmth, going against the grain to establish palpable tension early on. It never lets up, either. It just keeps tightening and tightening.

“Billie Jean” held the No. 1 spot on the Hot 100 in 1983 for seven weeks, starting an unprecedented run of commercial success for Jackson as a solo artist. Buoyed by his Motown 25 performance where he debuted the moonwalk dance move on live television in front of an estimated 47 million people, he and the track became a cultural phenomenon. It was the spark that fueled Thriller’s initial run of Billboard 200 chart dominance, too, spending 37 non-consecutive weeks atop that list. As of this writing, the album has been certified 34x Platinum in the US and has sold over 70 million copies globally. In 2008, the Thriller 25 reissue liner notes estimated that it still gets 250,000 spins every week in clubs. It wouldn’t surprise me if that number has grown, not ebbed, in the years since.

8. “Sweet Dreams (Are Made of This)” by Eurythmics (1983)

It’s fitting that we’re hitting “Sweet Dreams (Are Made of This)” in this slot, right after “Billie Jean,” since it signals an important shift in pop music as the mid-1980s inched closer. The warm, textural sounds of the 1970s had fully given way to something colder, more rhythmic, and utterly hypnotic. Like the Michael Jackson track, this arrangement doesn’t let you off the hook. The synth riff loops with a sense of resolution, creating a futuristic backdrop for Annie Lennox’s vocal, which itself is at war with itself, equal parts emotional longing and detachment.

By that point in their respective careers, Lennox and Eurythmics’ counterpart, Dave Stewart, were no longer a romantic item. They’d formed this duo out of the ruin of a previous group, the Tourists, and they were still spending hours and hours together in the studio. According to Lennox, Stewart wrote the lyrics to “Sweet Dreams” after the two had a big blow-up fight. “I thought it was the end of the road and that was that,” she said later. “We were trying to write, and I was miserable. And he just went, well, ‘I’ll do this anyway.’” For both their pop music fortunes, it turns out that was the right call

“Sweet Dreams” broke the group in the US after minimal success outside the UK, making both Lennox and Stewart into superstars basically overnight. The song reached No. 1 on the Hot 100 for one week, due in no small part to MTV’s parallel explosion as a promotional vehicle. Lennox’s visual presentation in the music video, with that bright, close-cropped orange hair and man’s suit, “broke the mold for female pop stars,” per the BBC. The Eurythmics would go on to have other global hits, but none that would attain the level of ubiquity as “Sweet Dreams.” The closest they’d come to No. 1 again would be with “Here Comes the Rain Again” in 1984.

9. “When Doves Cry” by Prince (1984)

Longtime readers will know I’m a Prince stan. He’s got one of the most impressive discographies of all time, of which Purple Rain is the undisputed centerpiece. That album, along with being one of the best film soundtracks ever made, is as much a science experiment as it is a work of pop music brilliance. There’s the existential dread of “Computer Blue” and the taut humidity of “Darling Nikki” that take the first side of the LP in fascinating directions. But no single song off Purple Rain demonstrates how peerless a songwriter and conceptualist he was in his prime as much as “When Doves Cry,” which ranks among his very best work.

It’s a song that’s missing a lot of familiar elements. There’s no bass line to speak of, just a kick drum and synth riff that cut through the negative space to sear themselves into your brain. Prince’s guitar work, including the whirling opening solo, is reminiscent of the late-60s psychedelic soul movement. The instrument provides an earthy element that sticks out like a sore thumb against the dry, aggressive rhythm that pulses underneath. Hovering over it all is the multihyphenate’s vocal, which careens between a howling falsetto and a lower, more suggestive register. The sum of all those parts is, somehow, some way, one of the catchiest songs I’ve ever heard.

“When Doves Cry” was the first single off Purple Rain and scored Prince his first Hot 100 No. 1. It stayed at the top of the chart for five weeks, one of several achievements that made 1984 an unparalleled success for him. The film of the same name grossed over $80 million domestically, and the soundtrack was eventually certified 13x Platinum. Prince accomplished all of this at the age of 25, by the way, which is an astonishing stat on its own. The level of creative control he maintained over everything— music, film, his visual identity, not to mention label negotiations—was a rare accomplishment even back then and may never be replicated to the same degree ever again. I don’t know what it was back in the 1980s, but music superstars were just built different then.

10. “What’s Love Got to Do with It” by Tina Turner (1984)

Tina Turner left Ike Turner in 1976 with nothing. No money, no house, no career momentum. She spent years rebuilding, playing small venues, and scraping together session work. I went over this backstory in more detail in my Private Dancer review, but the short version is that Capitol Records took a chance and signed her in 1983. That was the beginning of the resurgence that would see her become, at the time, the oldest women (she was 44) to top the Hot 100 with “What’s Love Got to Do With It.” It’s a testament to Turner’s sheer force of will in both the macro, meaning her career arc, and the micro, at the song level. This one wasn’t supposed to be as big as it became, but she made it so.

“What’s Love Got to Do With It” was initially offered to several other artists, including Donna Summer and Cliff Richard, who all passed on it for one reason or another. Turner didn’t like it at first, either, but her manager Roger Davies convinced her to try recording it. During the sessions that made up the work for Private Dancer, the track became more synth-laden and, compared to her ferocious R&B classics from the 1970s, more restrained rhythmically, which is the key to its appeal. Turner never overpowers the song, underplaying the question at the core of the lyrics. She’s not opposed to the idea of love, but she’s more than a little skeptical, and she sells both angles expertly.

Despite being one of the most celebrated R&B and rock singers of her generation, “What’s Love Got to Do With It” was Turner’s only No. 1 on the Billboard Hot 100. How is that fair and just in any way? She got close a couple of times, though. The Mad Max tie-in, “We Don’t Need Another Hero (Thunderdome),” and “Typical Male” both peaked at No. 2 in 1985 and 1986, respectively. Her story, which included building a brand-new persona that enjoyed plenty of air time on MTV and late-night talk shows, is one for the ages. If you haven’t seen the fabulous HBO documentary about her life, I highly recommend it. It will give you new appreciation for how important a pop music trailblazer she was.

11. “Time After Time” by Cyndi Lauper (1984)

Co-written by Rob Hyman of the Hooters, “Time After Time” is Cyndi Lauper at her least exaggerated and, one could argue, her most effective. She’s better known for fizzier pop cuts like “Girls Just Want to Have Fun” and “Money Changes Everything,” but this cut dials the everything back to the point where she has nowhere to hide in the mix. It’s a mechanism she’d redeploy with great success in the years after “Time After Time” (a song like “True Colors” comes to mind), but none of them have such an intuitive melody at their core. You could probably sing most of it back after one or two listens, which is further evidence that it works.

The press spent much of 1984 pitting Lauper against Madonna, trying to create this faux rivalry that, to my eye, seems built on nothing more than the fact that both women happened to have hit songs charting at the same time. But, where Madonna was far more calculating in her approach, Lauper always sounded like she was operating on a more instinctual level, and you can hear that in “Time After Time.” She wraps her words around that clean guitar figure like someone jotting down their innermost thoughts on lined paper, unbothered by letters or words that come out a little crooked or worm their way into the margins. It’s a much different, more honest kind of pop standard.

This single, the second of six (!) from She’s So Unusual, was the album’s only chart-topper. However, five of those six singles cracked the Top 10, setting a standard for debut LPs that few have equaled since. It’s been covered endless times in the years since and made it into just about as many films and TV shows as a reliable 80s needle drop, but perhaps the most striking bit of praise for Lauper’s classic came from jazz great Miles Davis, who covered it on his 1985 release You’re Under Arrest. He stripped it down to its essentials and the song lost none of its power. Talk about translating seamlessly to another medium …

12. “Everybody Wants to Rule the World” by Tears for Fears (1985)

Few songs in the 80s canon pull off a bigger misdirection than “Everybody Wants to Rule the World.” Everything in the arrangement signals warmth: the shuffle drum pattern, Neil Taylor’s jangly guitar figure with Roland Orzabal layering on additional parts, a bass line with a fluid, almost jazz-adjacent quality, and Curt Smith’s vocal, which is so indelibly clean and unforced. The whole track floats so effortlessly that it’s enough to make you forget what they’re actually talking about. If you’re paying attention to the title, you know the lyrical content is going to be anything but warm and fuzzy.

Tears for Fears were enthusiasts of Arthur Janov’s primal scream therapy from their formation (the band’s name is a play on one of his observations), and *Songs from the Big Chair* plays like existentialist psychoanalytic theater, wrapped in an immaculate collection of arrangements and production choices. They understood psychological tension better than most pop acts of the era, and I’d argue that “Everybody Wants to Rule the World” is their most elegant, accessible expression of it. The words by Orzabal, Ian Stanley, and Chris Hughes could be interpreted in any number of ways: Cold War commentary, Thatcherite critique, or a wry, somewhat weary observation about human ambition. Maybe all three simultaneously. But, crucially, the song never tells you which reading to choose, which makes the ambiguity a feature, not a bug.

“Everybody Wants to Rule the World” held No. 1 for two weeks in 1985 and won the Brit Award for Best British Single in 1986. The song has endured as, if not the “best” song of the 1980s, one of the most 80s to top the charts, with new generations of fans discovering it every few years. That legacy has helped their smash album go 5x in the US and sell over 9 million units worldwide. In a way, it’s an oddly comforting listening experience to this day, primarily because of the disconnect between what the production sounds like and what the songwriting conveys. It trusts the listener to sit with that gap, which is more than you can say for much of the pop music released during or since 1985.

13. “Take On Me” by a-ha (1985)

I don’t think it’s hyperbole to say the music video, as a medium, saved “Take On Me” and, by association, Norwegian synth-pop outfit a-ha from obscurity.

The first version of this song was released in 1984 with a different mix and a low-budget video, neither of which gained any traction with listeners. Warner Bros. then brought in director Steve Barron for a second attempt, commissioning the now-famous rotoscoped pencil-sketch animation that combined live-action with hand-drawn animation for an updated music video. The reshoot cost the label roughly $100,000 and took 16 weeks to complete. But, even at that price, the video is one of the most successful of all time, with over 2.4 billion views on YouTube alone (as of this writing).

I guess I’m underselling how strong the song is on its own terms, though. That synth riff, played on a Yamaha DX7, is one of the most recognizable of the decade, and I’d argue Morten Harket’s vocal performance gets far less credit than it earns. The sustained high note that closes the final chorus is a technical and emotional feat, sounding like someone overwhelmed by what they’re asking for (and hoping to give in return). The arrangement, which shifts between synth-driven verses and a guitar-inflected chorus, has more in common with power-pop than with their icier European contemporaries, making them sort-of outsiders in both the British and American markets. The fact that it’s tough to pin down in one single genre category is further proof of its greatness.

“Take On Me” held No. 1 for one week and, unsurprisingly, won six MTV Video Music Awards in 1986, including Best New Artist and Best Concept Video. The video deserved every award it won, but it also complicated the band’s legacy in a way they never fully recovered from. Underneath the animation spectacle is a simple, almost desperate love song, and the band, though they’ve remained popular, with a loyal fan base, in the years since, didn’t recapture that same fire after this moment. A tall order, but still.

14. “West End Girls” by Pet Shop Boys (1986)

Neil Tennant and Chris Lowe had an unlikely trajectory to pop stardom, to say the least. The former worked in publishing and later became a journalist, while the latter was pursuing a career as an architect. But after meeting at a hi-fi store in 1981, they immediately clicked and shortly thereafter started playing together. “We sort of released something in each other,” Tennant recalled of those early sessions. “There was immediately something there.” The duo built on their mutual interest in disco and electronic music, particularly pioneering acts like Kraftwerk and Depeche Mode. After Tennant flew to New York to interview Sting for Smash Hits magazine, he passed their demo to Bobby Orlando, an American producer who helped them cut “West End Girls” in 1984.

Except that’s not the version that would eventually top the Hot 100 for a week in 1986. That 1984 recording was a minor European club hit but didn’t sniff any crossover success. It wasn’t until EMI signed the duo and brought in Stephen Hague to produce that the single’s sound (and, by extension, the group’s sonic identity) began to really take shape. Besides his work with the Pet Shop Boys, Hague is best known for producing New Order and Erasure, and you can hear a lot of the same crisp confidence in the mix for “West End Girls.” Hi-hats snap and synths throb under Tennant’s lilting, somewhat disaffected vocal, with every element operating within clean lines, like lane dividers on an open highway. It’s a bit self-serious in its anxieties about class, money, and urban drudgery in Thatcher’s UK, but not enough to smother that iconic groove.

In addition to hitting No. 1 on the Billboard singles chart, the starmaking single was a big hit in Britain and across most of Europe. It ensured that Please, their debut studio album, also went Platinum. That LP is good, though I’m more partial to their follow-up, 1987’s Actually. That year, they also came the closest they’ve ever been to another No. 1, when “What Have I Done to Deserve This?” peaked at No. 2. What gets me about “West End Girls” is how fully fleshed-out the group’s emotional register (loneliness disguised as sophistication) was at the outset of their career. Nobody writing pop songs in 1986 was doing anything quite like it.

15. “Livin’ on a Prayer” by Bon Jovi (1987)

I’ve never understood the Bon Jovi hate.

Sure, they’ve made their fair share of cornball, lowest-common-denominator rock songs, but that’s only part of the bigger picture. In over 40 years in the business, they’ve accumulated a deep, critically underrated catalog that has produced 4 separate No. 1 hits on the Hot 100, all of which topped the charts between 1986 and 1989. Not dissimilar to Coldplay, it may be trendy to hate on Bon Jovi, but all the snobbery in the world can’t take away the fact that those boys from New Jersey, along with writer Desmond Child and producer Bruce Fairbairn, created a song so universally adored, so embedded in our everyday lives, that people will sing it anytime, anywhere. Sometimes, they’ll even do it in the presence of Jon Bon Jovi himself.

At this point, when someone says the words “Livin’ on a Prayer,” you can hear it in your head immediately. The opening synth note gives way to that infectious bass line. The talk box, gated reverb on those drums, and the massive key change that hits you right in the feels every time that final chorus starts. It’s 80s feathered hair euphoria. All those ingredients combine to make it one of the most effective stadium anthems in pop-rock history, with a mix that’s loud and engineered for maximum sonic impact. Underneath all its sheen, you have a doomed working-class love story that, even though we’ve never met Tommy and Gina, presents instantly familiar archetypes. They’re holding onto each other because they literally have no other option, and, in a sad way, exemplify a lot of what the “American Dream” has come to stand for.

Jon Bon Jovi has said in multiple interviews that he didn’t think the song was strong enough to merit consideration for Slippery When Wet, the blockbuster album that turned the group into global superstars. He and the rest of his bandmates initially passed on recording it, but manager Doc McGhee and others pushed for its inclusion. It ultimately became the second single from Slippery When Wet, building on the momentum generated by “You Give Love a Bad Name,” which also went to No. 1. “Livin’ on a Prayer” held the top spot for four weeks and has since accumulated over 2.2 billion Spotify streams, more than any other 80s track on the platform.

16. “I Wanna Dance with Somebody (Who Loves Me)” by Whitney Houston (1987)

By 1987, Whitney Houston had already scored multiple No. 1 hits and was well on her way to becoming one of the most dominant voices in 80s and 90s pop music (spoiler: this won’t be the last time we hear from Whitney in the Summer of Billboard series). But, of those early hits, most of them put her in a specific balladeering lane that was putting an artificial glass ceiling over her enormous potential. Clive Davis and her production team made it their mission to craft a signature uptempo song that would put her in another, rarified pop diva category, and set about writing and recording what has endured as one of her greatest achievements, “I Wanna Dance with Somebody.”

Following the success of “How Will I Know,” a track that I adore and that very nearly supplanted this one as this list’s Whitney Houston entry, Davis brought back George Merrill and Shannon Rubicam to craft a sequel of sorts. The duo penned “Waiting For a Star to Fall,” another one of my favorite 80s songs that they’d release under their own banner, Boy Meets Girl, but Davis and company passed on it for Whitney’s upcoming album. “We wanted to write a song that was airtight, that was just so solid on its own, it could be an uptempo [track], it could be a ballad, it was just going to be,” explained Rubicam. The vocal melody invites Whitney to make a meal out of it, and she does just that, delivering a performance that’s technically extraordinary and yet so airy and effortless-sounding.

The other architect that needs to be mentioned is Narada Michael Walden, who built the arrangement around a driving synth-pop beat not dissimilar to the one he produced for Aretha Franklin on “Freeway of Love.” Walden’s press quotes about working on this song are, um, interesting, especially when it comes to moving Whitney’s sensibility away from the “white pop” aesthetic she often got accused of pandering to. It’s a crude description perhaps, but I think Walden sums up the instrumental’s appeal perfectly here: “My philosophy is the outhouse bottom with the penthouse view... if it’s got nastiness on the bottom, which is really funky, but it’s very pretty on top, that combination is kind of irresistible.”

The song held at No. 1 on the Hot 100 for two weeks in 1987 and won the Grammy for Best Female Pop Vocal Performance.

17. “Father Figure” by George Michael (1988)

And now, for something completely different. A track that I’d posit is one of the most anti-No. 1 No.1 hits in the history of the Billboard Hot 100: George Michael’s “Father Figure.”

Everything about it resists Top 40 conventions of the period, maybe the biggest reason it’s held up better than most of what surrounded it on the charts. The running time exceeds five minutes. The tempo is unhurried and never sounds like it’s working too hard, least of all to wow the listener. More importantly, George Michael wrote, produced, and arranged the entire track himself, a workload that he certainly wasn’t forced to undertake. He was at the height of his immediate post-Wham! fame and could’ve done whatever he wanted. Instead of following the day’s trends to a T, he created a track that reflects a more eclectic taste.

The programmed drum pattern soothes rather than thumps, the bass synth sits in a sunnier register than you’d think, the strings swell with the perfect amount of intensity, and there’s even a jazz-inflected guitar that adds to the laid-back atmosphere. The arrangement owes more to 70s soul and to records like Marvin Gaye’s “I Want You” than to anything else that graced the Hot 100 in 1988. Michael was just 24 years old when he made “Father Figure,” a love song that sits in this transfixing space between tender and unsettling. You could say the same for other tracks off Faith, his teen-pop emancipation statement, such as “I Want Your Sex,” but the strangeness of the lyrical premise is unlike anything on that LP and, more broadly, in that era of his career.

“Father Figure” held No. 1 for two weeks, the fourth of six singles from Faith to reach the Top 5 in the US. The parent album also topped the Billboard 200, won the Grammy for Album of the Year, and has been certified 10x Diamond (it’s sold over 25 million copies worldwide to date). I’ve always considered George Michael’s solo career a bridge between the blue-eyed soul tradition of Hall & Oates and the neo-soul movement of the 1990s. He sang with so much feeling, even when he was purposely holding the theatrics back considerably. I have a feeling his catalog will age incredibly gracefully as the decades pass.

18. “Sweet Child o’ Mine” by Guns N’ Roses (1988)

Slash’s legendary riff for “Sweet Child o’ Mine” was supposedly conceived as he was noodling with a circular guitar figure he later described as a “circus melody” during rehearsal. He was playing it as a warm-up joke, nothing more, but when Duff McKagan and Steven Adler heard it, they immediately moved to lock in a groove underneath. Izzy Stradlin’s rhythm guitar provided the chordal foundation that let Slash’s lead line float. Axl Rose, hearing what was taking shape, started writing a lyric. The story of how this song came together is almost a parable about how the best accidents happen: you can’t will a riff like this one into existence. You have to let it sneak up on you.

More than anything else, “Sweet Child o’ Mine” is what brought Guns N’ Roses the kind of mainstream success they hadn’t necessarily banked on. It’s often lost to time now, but the truth is that Appetite for Destruction, took over a year to find its audience commercially. “Child” was the third single and the one that finally helped push the LP to the top of the charts (the song itself held the No. 1 position for two weeks and is, to date, the band’s only US chart-topper). Rose wrote the lyric about his girlfriend Erin Everly, daughter of Don Everly of the Everly Brothers. The specificity of the imagery, her eyes, her smile, the way she takes him to a calmer place when the noise in his head gets too loud, is reminiscent of country-rock ballads from the likes of the Allman Brothers Band and Lynyrd Skynyrd, the latter of which served as inspiration for GN’R to infuse the track with “that heartfelt feeling.”

GN’R arrived at a moment when hair metal had largely calcified into posturing and tired formulas. While they may have leaned into similar era-specific instrumentation, they had a different energy, rooted in the traditions of the Stones and Aerosmith rather than post-glam-rock preening. To that end, “Sweet Child o’ Mine” is a rock music Trojan horse, boasting a framework that’s melodic enough for pop radio, but also dangerous enough to introduce more casual listeners to a band that had no interest in being palatable with any consistency. Appetite is one of the most transcendent feel-bad albums ever made thematically, and, as I argued in the discography ranking, it’s also in the conversation for the best debut LPs of all time, regardless of genre.

19. “Like a Prayer” by Madonna (1989)

I’ve written a fair amount about Madonna in this newsletter (her albums ranked across three installments), and one of the arguments I keep returning to is the disconnect between how calculated her image could be and how unguarded she sounds on her best recordings. “Like a Prayer” is arguably the most famous of those case studies and, for me, the most endlessly listenable of them all.

At the end of the 1980s, Madonna was at a crossroads. She was one of the biggest stars in the world across music, film, and the stage, but she was also coming off several commercial flops in a row and freshly divorced from Sean Penn. Out of that emotional turmoil came a song and album (which I wrote about here) that wraps its arms around a whole lot, including the prevailing guilt the Catholic church saddles many of its constituents with for life. “In Catholicism, you are born a sinner and you are a sinner all of your life,” she told Rolling Stone in 1989. “No matter how you try to get away from it, the sin is within you all the time.”

Here’s more about the song from my original review:

“Much has been written about how [’Like a Prayer’] courted controversy and set dubious standards for capitalistic opportunism to the point where the magic of the music itself has been at least partially obscured over time. The start-and-stop minimalist rhythm gives Madonna room to work through deep-rooted struggles [and] whether she’ll ever truly feel one with [Him]. Phrases like ‘I want to take you there’ and ‘I can feel your power’ feel at odds with the more paranoid lyrics (’It’s like a dream/No end and no beginning’). Does this track confirm her allegiance to a higher power or show her rejecting it in favor of a more grounded (these days, it’d be phrased as ‘woke’) worldview that celebrates individualism?”

It’s another kitchen-sink single that, when dissected, maybe shouldn’t work on paper. There’s the church organ that arrives first, the Andraé Crouch Singers (one of the most respected gospel choirs in the country), some rock guitar swirling over a funk bass line, and somehow it doesn’t collapse under its own weight. Nearly 30 years later, it still soars.

20. “My Prerogative” by Bobby Brown (1989)

Bobby Brown left New Edition in 1985. He was 17 and, by all accounts, primed for stardom. The swerve? His first solo album, King of Stage, from 1986, was a flop. Softer production and languid pacing kill what could’ve been a much more interesting record, leaving Brown frustrated with the overall sound. He elected to go with different, more proven producers for a follow-up, linking with names like Babyface, L.A. Reid, and Teddy Riley, all of whom have been discussed in this newsletter before. That album, Don’t Be Cruel, would go on to sell upwards of 12 million copies, further popularize New Jack Swing, and give him his only US No. 1 single, “My Prerogative.”

Riley’s production is bonkers. The drum programming is harder and more syncopated than almost anything on mainstream R&B radio at the time. Control is certainly in that conversation, but even Jam & Lewis beats weren’t as thick and brawny as this one. Over top, the synth stabs are also aggressive, almost confrontational in nature. Riley was borrowing from hip-hop’s burgeoning vocabulary while retaining enough melody for pop radio, a hybrid that would dominate and reshape pop in the first half of the 1990s. Lyrically, “My Prerogative” sets a template that’s been reused time and again in the rap game, from his New Jack contemporaries to men on both sides of the Drake/Kendrick beef: a direct response to tabloid scrutiny and public judgment. Rejecting the premise means you’re controlling the messaging.

“My Prerogative” reached No. 1 for one week in early 1989, one of five Top 10 singles produced by Don’t Be Cruel’s run of success. Alongside Janet Jackson’s Rhythm Nation 1814, it also signaled the beginning of an era in which one smash hit album could mean two-plus years of chart and media visibility through MTV, award show performances, and so on. Brown also won the Grammy for Best Male R&B Vocal Performance, showcasing the commercial opportunity that came with bridging polished R&B vocal-group stylings and a rough-edged hip-hop persona.

He wasn’t a rapper, but he moved through the culture like one.

Which 1980s No. 1 would you have added? And which one on this list are you putting on right now?

The 1970s were undoubtedly one of the best decades for the Hot 100. So many timeless songs full of warmth, texture, and emotional depth, but also plenty of strange, shiny objects that

Think about this: Over a 10-year span, the same weekly music survey crowned Stevie Wonder, Marvin Gaye, Carl Douglas (of “Kung Fu Fighting” fame), Andy Kim (“Rock Me Gently”), and the Osmonds as chart-topping artists. Tony Orlando made it to No. 1 three separate times, for god’s sake. A little something for literally everyone, you know?

Anyway, canvassing the Hot 100 entries of the 1970s meant re-listening to plenty of protest anthems, disco floor-fillers, country-rock crossovers, Swedish pop architects, and at least one song about kissing someone all over that has no business being as good as it is (we’ll get to that shortly).

As with every other installment in this Billboard Hot 100 series, this isn’t your standard “best of the 70s” list. It’s a collection of 20 songs that have left the greatest impression on me in my life as a music nerd, and also happened to hit No. 1 between 1970 and 1979.

Plenty of great 70s songs never topped the chart, by the way. “Bohemian Rhapsody” peaked at No. 9, “More Than a Feeling” at No. 5, and “Born to Run” at No. 23. And plenty of other No. 1 hits from the decade have aged about as well as whatever this Gary Glitter performance was.

These 20 songs fall somewhere in between, in the best possible way. Same rules apply: One song per artist, with each track selected for lasting musical, cultural, or emotional impact, not chart performance alone.

If you’re new here, the 1960s installment is already up. Paid subscribers also get the companion playlists for my favorite 100 recordings from each decade, one song per artist as well.

Smash the button to skip to the playlist and, if you’re so inclined, upgrade your subscription to access.

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In chronological order, let’s go:

1. “Bridge Over Troubled Water” by Simon & Garfunkel (1970)

Let’s start this list off with a genuine 10/10 No. 1 song.

I first heard “Bridge Over Troubled Water” when I was 12 or 13, before I had any concept of who exactly Paul Simon and Art Garfunkel were, or what the duo meant to the evolution of pop music as the tumultuous late-60s gave way to a new decade. On first, second, and third listen, it bowled me over with how it builds to this incredible, overpowering emotional crescendo. It starts at almost a whisper and ends with one of the most cathartic final notes of all time. It’s flat-out one of the most beautiful songs I’ve ever heard.

This song is also a fascinating “almost” in Simon’s career. He wrote the song, co-produced it with Roy Halee, and sang it on the demo track. Garfunkel, who was by that point mostly estranged from his longtime musical partner, didn’t think he was a good fit for the vocal, but Simon insisted. It turned out to be the right call. Gartfunkel is the absolute perfect choice for such an expansive, penetrating gospel track. After Larry Knechtel’s piano sets the tone, there’s no one else you want to hear carry you through to his last sweeping proclamation.

Despite initially chaffing the label as too slow and cerebral a single choice, “Bridge Over Troubled Water” ended up being one of the biggest songs Paul Simon ever released. It held No. 1 for six weeks and swept five Grammys, including Record of the Year and Song of the Year. The eponymous album, another of my all-time favorites, spent 10 weeks atop the Billboard Album Chart. Simon supposedly resented that Garfunkel’s performance became the most celebrated moment of their career together. Thankfully, none of that tension is audible.

2. “War” by Edwin Starr (1970)

“War” is one of the most incendiary protest songs of all time—so incendiary, in fact, that Motown head honcho Berry Gordy was initially unwilling to release it as a single. The label had already recorded the song with the Temptations, who semi-buried it on the tracklist for Psychedelic Shack. Their version is controlled and smooth, the kind of political statement you can acknowledge and nod along with, only to file it away and forget about it in short order. Starr’s rendition runs in the complete opposite direction.

His voice sounds like it’s holding on for dear life. The growl-and-shout delivery, accentuated by those “good God y’all” interjections, breathes such vitality into the call-and-response structure. The horns practically function as percussion rather than melody, with those iconic stabs standing taller than any snare or kick drum could. All of it creates something that sounds less like a pop single and more like a man losing his mind in real time, being driven mad by America’s undeniably pointless show of force in Vietnam, a war that claimed millions of innocent lives.

The record held the No. 1 spot on the Hot 100 for three weeks and became the most commercially successful spit-in-your-eye moment in American chart history at the time. The bluntness is still shocking today. “War, what is it good for? Absolutely nothing.” No metaphor. No poetry. No “both sides” nonsense. That’s why it works. Now, the question is, where are these types of songs speaking out against injustice and violence today?

3. “Family Affair” by Sly and the Family Stone (1971)

Beneath the funk, beneath the laconic Sly Stone vocals, there’s a haunting, cynical resignation that powers “Family Affair,” the single that would sadly be their last trip to the top of the Hot 100. It’s got a fun groove at its center, but the song is also eerily still, putting you in this inert state in the middle of a party that’s losing steam. You can read that as a metaphor for the end of the progressive, activist-minded 1960s, or another for Sly’s descent into addiction that would kill his career shortly after this success, his biggest on the pop charts. All those are true.

“Family Affair” was seen as a comeback of sorts for the group, which hadn’t released a proper studio album for two years. Minus the double A-sided single “Thank You (Falettinme Be Mice Elf Agin)”/ “Everybody Is a Star,” the band had mostly fractured and left the public eye. When they did reconvene for this single’s parent album, There’s a Riot Goin’ On, the bad vibes were real. It divided both critics and fans, and signaled that maybe, just maybe, the fantastic run they’d enjoyed for much of the past half-decade was over.

This song, with its stripped-back production that included the first usage of a drum machine on a pop chart-topper in the US, is a deliberate reversal of everything Sly had done previously. His voice is half-whispered and deeply narcotized. The communal joy of his earlier records had curdled into a stew of paranoia, missed gigs, and broken relationships. Sly recorded much of the album alone, maybe because only he was interested in trying to recapture what he’d lost.

It’s arguably the first major hit that sounds like the aftermath of the 1960s, rather than a continuation of that decade’s optimism.

4. “Just My Imagination (Running Away with Me)” by The Temptations (1971)

I’ve sung the praises of the Temptations multiple times in this newsletter, but none of their ballads hit my vintage soul sweet spot quite like “Just My Imagination (Running Away with Me).” I actually found this song first through the Rolling Stones’ 1978 cover that graced the Some Girls tracklist, before I had any notion of who the Temptations were, not to mention the Motown group’s behind-the-scenes svengalis, Norman Whitfield and Barrett Strong. But, with hindsight and a much more nuanced musical palette, there’s no comparison. This ballad is one of the most gorgeous hits of the 1970s, regardless of genre.

What’s most interesting is that it went to No. 1 while the Temptations were in the thick of their psychedelic funk reinvention. Their songs had become more sonically complex and, from a songwriting perspective, much more socially conscious. There was little indication they would return to anything approaching their signature 1960s sound, and fans were “screaming bloody murder,” according to lead singer Eddie Kendricks. Finally, Whitfield relented and agreed to produce the airy, wistful love song that would mark the last Temptations single to top the Hot 100.

There’s a deeper thematic angle to “Imagination,” too, which is the dissolution of the group’s “classic five” lineup. Kendricks, whose floating falsetto gives the track its wings, left the Temptations before the single was released to begin a solo career. Paul Williams was forced to retire shortly thereafter due to health problems stemming from sustained substance abuse. The bittersweet aspect of every audible element reaches back into the history of soul music in more ways than one.

5. “Theme from Shaft” by Isaac Hayes (1971)

Everything about this song sounds incredible.

That wah-wah guitar. Those hi-hats. The orchestral swells and stabs. It’s central groove, which has become one of the most admired, imitated, and sampled in funk, R&B, and hip-hop history. If you’re a fan of his like I am, then you’ll know that “Theme From Shaft” is one in a long line of examples of what Isaac Hayes did better than any of his contemporaries: build an atmosphere before a single word is uttered. Honestly, you probably don’t really need words in this one at all, though I can’t deny the appeal of those “shut your mouth” moments when they’re sighed into the mic.

At that point in his career, Hayes was already a legend and didn’t necessarily need the film soundtrack on his resume to prove it. He’d co-written some of Sam and Dave’s biggest hits and basically saved Stax Records from going under all by himself. But when he moved to film scoring, he took his critical and commercial returns to another level, becoming, among many other things, the third Black person in history to win a competitive Oscar (Best Original Score) and the first to win for music.

In my original review of the soundtrack, I noted the following on its legacy:

“A lot of the records I’ve discussed in this newsletter can trace their DNA back to Shaft […] From neo-soul and alternative R&B to hip-hop subgenres like G-funk and trap, Hayes’s cultural contributions make those endpoints feel inevitable in hindsight. His work on this soundtrack was the spark that would set the charts ablaze with categorically Black influence. His was a sonic declaration that power, style, and storytelling didn’t have to compromise to make their mark. They could strut, burn, and groove, all on their own terms. More than anything else, that commitment to one’s art is why I consider Hayes to be a genius.”

“Theme From Shaft” stayed at No. 1 on the Hot 100 for two weeks.

6. “Lean on Me” by Bill Withers (1972)

Like Ray Charles before him, Bill Withers’ voice can reach deep inside your soul and ignite memories or emotions you didn’t think were possible. Withers often did this through sparse, universally singable melodies, including his first hit, “Ain’t No Sunshine,” “Use Me,” and “Grandma’s Hands.” There’s a lived-in groundedness in a Bill Withers song that you can’t fake and, as a result, can’t easily replicate either.

The best case study for the latter phenomenon is “Lean on Me,” which held down the No. 1 spot on the Hot 100 for three weeks in 1972. It’s arguably the simplest song on this list, made up of piano, bass, drums, voice, and handclaps. But simple in this case doesn’t mean dumbed down or uninteresting. Instead, it’s a relentlessly hopeful song, inviting those listening to come together and find the strength to push through seemingly insurmountable adversity. “We all have sorrow,” Withers sings in the first verse. “But if we are wise, we know that there’s always tomorrow.”

“Lean on Me” has permanently etched its music and words into the pop culture lexicon, with nearly 300 officially documented covers released as of this writing. Big names have tried their hand at this Withers hit, too, including Tom Jones, Al Jarreau, Michael Bolton, Seal, and Glen Campbell, among them. The Club Nouveau version went to No. 1 again in 1987, adding even more depth to its legacy. Amazingly, this song was Withers’ only chart-topper as a solo artist, though he got close a couple of times. “Use Me” and “Just the Two of Us,” his collab with Grover Washington Jr., both peaked at No. 2.

7. “Let’s Stay Together” by Al Green (1972)

Friends, it’s time. I’m so excited. We get to spend a few minutes discussing one of my favorite singers and songs of all time: Al Green’s “Let’s Stay Together.”

Beginning in the late-1960s, the Arkansas native enjoyed one of the most celebrated runs of any soul and R&B artist during the first half of the 1970s. With his expressive falsetto, his catalog includes all-timers like “Tired of Being Alone,” “Love and Happiness,” and “Take Me to the River,” the latter of which eventually became a hit for the Talking Heads. But Green’s crowning achievement is undoubtedly “Let’s Stay Together,” which only stayed at No. 1 for a week in 1972 but stayed on the chart for 16 weeks. It was reportedly the 11th biggest-selling song of that year.

The track’s music was conceived by Willie Mitchell, a Hi Records producer who worked with several notable Memphis artists, and Alan Jackson Jr., who was primarily known as a session drummer. Mitchell’s philosophy of using negative space effectively in the mix is a key component of “Let’s Stay Together.” Each element in the mix has room to breathe and carve out a sonic niche for itself over the three-minute runtime. No one aspect of the song tries to dominate the others, making it all sound so smooth and seamless.

After hearing a demo from Mitchell and Jackson, Green wrote the lyrics quickly and, for a brief moment, wasn’t all that interested in recording it. He believed the song was a little too conventional compared to what he’d released to that point in his career. It ended up being his most significant outing as a solo artist, leaning into the unfussy Memphis soul aesthetic as a counterpoint to Philadelphia’s lush orchestral productions and Motown’s pop machinery. It’s influenced everything from quiet storm radio to modern neo-soul.

8. “Midnight Train to Georgia” by Gladys Knight & the Pips (1973)

The backstory for “Midnight Train to Georgia” is a delightful little game of six degrees of separation, 1970s edition.

The song was penned and originally performed as “Midnight Plane to Houston” by Jimmy Weatherly, an ex-NFL prospect who turned to songwriting after those initial plans didn’t work out. Weatherly played in a rec football league with Lee Majors, who later inspired one half of the couple at the heart of the song’s narrative. The other half? Majors’ then-girlfriend Farrah Fawcett, when the lyricist phoned their home one night and asked what she was up to, told him that she was taking the red eye that gave the track its first title. Weatherly’s recording eventually found its way to Cissy Houston, for whom Weatherly agreed to change the mode of transportation to a train and the destination to Georgia.

After Houston released the song as a single in 1973, Weatherly’s publisher forwarded that version to Knight, who had just moved from Motown to Buddha Records and was looking for material for what became 1973’s excellent LP Imagination. She changed the tone and timbre of the instrumental, going for a warmer, Al Green-esque backdrop for the story’s bittersweet homecoming. The call-and-response interplay between her and Pips gives the single an exquisitely timed, almost Greek chorus kind of feel. Even though the protagonist has crashed and burned trying to make it in Los Angeles, the woman telling the story is more than happy to stick with him in his return. “I’d rather live in his world than live without him in mine,” she coos.

“Midnight Train to Georgia” held the No. 1 spot on the Hot 100 for two weeks and, in 1974, won the Grammy for Best Pop Vocal Performance, beating out a stacked list of competitors for that distinction, including Stevie Wonder’s “You Are the Sunshine of My Life.” It’s also been a consistent film and TV needle drop, heard in works like The Deer Hunter, Broadcast News, and 30 Rock.

9. “Superstition” by Stevie Wonder (1973)

Almost everything you hear on “Superstition” is played by Stevie Wonder. That includes the Hohner Clavinet riff that’s become one of the most recognizable in pop music history, the Moog bass, and the drum pattern, which apparently came from renowned guitarist Jeff Beck. Wonder had originally intended for Beck to record the song as a thank-you for his contributions to Talking Book, but when Motown head Berry Gordy smelled a monster hit, he demanded that Wonder lay down his own version and release it as a single. By the time its parent album was released, “Superstition” had already stormed the pop and R&B charts, becoming one of the 1970s’ most memorable crossover No. 1s.

It’s weird to think of this track as a fusion piece, but there’s more than a little rock mixed in with the funk sensibilities on display. We can chalk that up to Wonder’s willingness to experiment with different song structures, his time spent touring with the Rolling Stones in 1972, or his growing sense of how to craft propulsive hooks. Everything here moves so well, from the punchy horn arrangements to the tension that builds during the bridge, the only moments where the groove pauses to let you catch your breath for a split second. It’s pre-disco as a saturated radio and nightclub movement, and yet it’s one of the most universal dancefloor fillers of all time.

“Superstition” also comes smack in the middle of Stevie Wonder’s classic period, his unassailable stretch from 1972 to 1976 that saw him drop one extraordinary LP after another, including Music of My Mind, Innervisions, and Songs in the Key of Life. Though it only held the top spot for a single week, this track was his first in a string of US chart-toppers that, by decade’s end, would write his name in the history books.

10. “You’re So Vain” by Carly Simon (1973)

More than 50 years after it became a smash, (almost) no one knows who “You’re So Vain” is really about. We do know a few names that can be crossed off the list, such as Mick Jagger (who provided uncredited backing vocals during the recording), James Taylor, and novelist Nicholas Delbanco, whom Carly Simon had dated for a time in the 1960s. The singer/songwriter does like to tease the man’s identity cryptically in her music, though, telling WYNC that she supposedly hid the name in a 2009 re-recording of the classic track. The closest we’ve ever come to an answer was in 2015, when Simon admitted the second verse is about Warren Beatty.

But it doesn’t really matter who she’s describing in her lyrics because, at the end of the day, it’s really a putdown of a specific kind of man. The kind of narcissist who most people will recognize without needing to put a name or a face to. It’s the perfect balance of personal and universal, one that helped “You’re So Vain” stay at No. 1 on the Hot 100 for three weeks, a streak that propelled her album, No Secrets, to the top of the album chart. The chorus alone is a masterstroke. Think about it: “You’re so vain, you probably think this song is about you.” If the subject recognizes himself, he proves her point. If he doesn’t, well, she still wins.

What gets lost in the lore and rumor mill surrounding the song’s content is how sophisticated the production is. The opening bass jangle, which bleeds into a slinky piano figure, puts you off-balance from the first few seconds. The arrangement is a deft blend of pop, soft rock, and breezy bossa nova, with a Simon vocal that’s more knowing and amused than bitter. The sum of those parts is a breathtaking bit of confidence, showcasing a female artist who understands her leverage point and is taking her sweet time about it. Few pop lyrics have ever been this airtight, even if it endures partly as a pop culture riddle.

11. “Fame” by David Bowie (1975)

Despite his global popularity, David Bowie only cracked the Top 10 of the Hot 100 twice in the 1970s. Curiously, both of them came from his Thin White Dukes days—Young Americans and Station to Station, to be specific. Even more intriguingly, those two songs are among the least “rock” he’d ever presented himself as to that point. I know some in his online fan circles will quibble that his “plastic soul” phase was a purely commercial ploy, but, with that said, there’s no denying that “Fame” is one of the coolest, most confident songs he’s ever released.

The two standout supporting names on this track are Carlos Alomar, whose slinky guitar riff gives the arrangement its engine, and John Lennon, who is officially credited as both a backing vocalist and a songwriter. By 1975, the Beatles had been broken up for half a decade, and Lennon’s solo catalog had devolved into a weird, lovesick miasma. As I said in my original review of the song, “I have a suspicion that, lyrically, this track reflects both men’s dissatisfaction with the baggage that comes with fame, [from] two-faced management to relationships bending under the weight of ego and substance use […].”

The irony is thick: A white British art-rocker topping the American charts with a funk track recorded at a Philly soul studio. The sentence alone tells you how wild the mid-1970s were. The song is about fame as a corrosive force, yet Bowie was chasing that very thing while describing its damage. The performance sounds like both impulses colliding in real time.

12. “Jive Talkin’” by Bee Gees (1975)

I guess this entry is where my list of favorite Hot 100 No. 1s of the 1970s leans fully into the disco craze. Kind of. I say that, knowing full well that my intro from my piece touting the Bee Gees as GOAT songwriters warns against that kind of reductive framing. However, seeing as I didn’t cover “Jive Talkin’” in that initial article, it’s only fair to give the brothers Gibb a little more shine, especially considering this song singlehandedly turned their fortunes around and helped make them one of the best-selling music acts of all time.

The first half of the decade had been absolutely brutal for the group. Their 1960s cultural cache had dried up, they’d been dropped by their management group, and 1974’s Mr. Natural had been a commercial disaster. Their producer, the great Arif Mardin, pushed them towards a more R&B and funk sound, and it was Barry Gibb who found the bones of the rhythm driving across the Julia Tuttle Causeway in Miami. Throw in some Caribbean influence and one of the earliest uses of a synth bass on a pop record, and you have one of the most important songs of its era.

“Jive Talkin’” held No. 1 for two weeks in 1975, giving the group their first chart-topper since 1971, and paved the way for everything that would come with the Saturday Night Fever explosion. It was also one of the last times Barry sang in his chest voice rather than his iconic falsetto, solidifying the before-and-after sliding doors at work here. With their disco reinvention waiting in the wings, it’s undeniable that, without this record, there’s no “Stayin’ Alive,” no “You Should Be Dancing,” and a pop music landscape that looks totally different post-1975. One that would look much less vibrant, if you ask me.

13. “Lady Marmalade” by Labelle (1975)

If you need any more proof that the 1970s were absolutely bonkers, consider that three Black women in space-age costumes got a song about a New Orleans sex worker to No. 1 on the Hot 100.

Before that happened, the song was recorded by the Eleventh Hour, a disco group fronted by one of the song’s co-writers, Kenny Nolan. He and the other scribe, Bob Crewe, had penned the lyrics after a visit to New Orleans, with the risque inclusion of the French-language proposition used as the chorus’s iconic hook, fitting right in with the lurid lore of the city’s red light district. Nolan’s initial version didn’t chart, but it eventually made its way into the hands of producer Allen Toussaint, who, besides this hit single, is best known for his work with Dr. John and the Meters.

The latter funk outfit provides the rhythmic backbone and it sounds so, so, so smooth right out of the gate. Art Neville’s Hammond organ comes at you as if through a plume of cigarette smoke, while George Porter Jr. gives the arrangement plenty of stomp on the bass. On vocals, flanked by Sarah Dash and Nona Hendryx, Patti Labelle is in fine form, especially when she’s extracting every last syllable out of the word “marmalade.” Apparently, she had no idea about the song’s true subject matter, which is either a lie or so adorable I can’t stand it. I grew up learning French in school, so I guess I take bilingualism for granted, but still. Too funny.

Labelle’s version of “Lady Marmalade” went to No. 1 for one week in 1975 and was the group’s only chart-topper. Patti left the group a couple of years later and, as of this writing, is still keeping a robust tour schedule at age 82. As for the song itself, it’s been covered and sampled dozens of times, most famously by Christina Aguilera, Lil’ Kim, Mya, and Pink as part of the Moulin Rouge! soundtrack in 2001. Durability, confirmed.

14. “You’re No Good” by Linda Ronstadt (1975)

Linda Ronstadt had been building toward “You’re No Good” for most of the early 1970s. She’d been releasing country-rock records since 1969, none of which broke through commercially in any meaningful way despite proving her voice was extraordinary. She began playing this song live more than a year before it was recorded, using it to close her sets while she opened for Neil Young on tour. By pure coincidence, Ronstadt’s producer on Heart Like a Wheel, Peter Asher, was also a massive fan of the tune since the early-1960s. Despite being a last-minute addition to the tracklist, it became the singer/songwriter’s signature song, all by zigging where the original zagged.

Written by Clint Ballard Jr., who appeared on the list of my favorite Hot 100 No. 1s of the 1960s, “You’re No Good was first recorded by Betty Everett in 1963. It’s a perfectly pleasant R&B single with a strong melody, but it has nowhere near the bite that Ronstadt’s version does. Her vocal is much more authoritative, seething with anger rather than wallowing in heartbreak. That switch changes the entire dynamic of the story. Instead of a soft, perhaps overly forgiving assessment of the central relationship, Ronstadt is unapologetic in its stance. If I’m not good enough for you, then get out.

Andrew Gold’s electric piano and guitar work give the arrangement a steely crunch that earlier versions lacked, and Asher kept everything around them as hard-edged and unadorned as he could, all without obscuring his star’s gravitas. “You’re No Good” held No. 1 for one week in early 1975and helped Heart Like a Wheel eventually go double platinum. Ronstadt was on her way to becoming the biggest-selling female rock artist in America, and this record explains that appeal.

15. “Don’t Leave Me This Way” by Thelma Houston (1977)

For years, Thelma Houston was a Motown act that was kind of just around. She wasn’t bad by any means, but she’d been at the label since the late-60s and had little commercial success to show for her efforts. However, as it did for so many other “almost” acts, disco gave her a second chance when Hal Davis brought her a Philadelphia soul song that had already been released and largely forgotten. What Davis did with the same composition is one of the cleaner examples of how production context can rewrite what a song actually is.

The original (which is also a banger) was written for Harold Melvin and the Blue Notes by Kenny Gamble, Leon Huff, and Cary Gilbert. Teddy Pendergrass was on lead vocals. It’s a slow-burn funk jam, where Pendergrass’ restraint presents the listener with its own kind of drama. By contrast, Houston’s version runs the same song through a different machine. The tempo accelerates, the strings are front and center rather than buried in the mix, and the four-on-the-floor drum groove is locked all the way in. What had previously been a more plaintive Blue Notes outing was suddenly a dance floor event.

The record remains Thelma Houston’s only significant chart success. It held at No. 1 on the Hot 100 for one week in 1977 and later won her a Grammy for Best Female R&B Vocal Performance. Unfortunately, the label never quite figured out how to follow up on it, though she’s released a dozen studio albums since this commercial apex. Hers wouldn’t be the last career resurrected with the same disco-centric formula: same composition, different emotional temperature, instant exposure to a mainstream audience.

16. “Dancing Queen” by ABBA (1977)

What more is there to say about “Dancing Queen” other than it’s one of the most beloved pop songs of all time?

I said as much in my piece about ABBA’s prolific, largely unequaled career as European hitmakers who took over the US charts in their heyday.

Here’s an excerpt:

*Subjective sentimentality aside, it’s hard to come up with a long list of songs, past or present, with a melody as uplifting or a spirit as pure as this one. Throw in some first-rate production from the group’s chief architects, Benny Andersson and Björn Ulvaeus, and bright, layered harmonies from Agnetha Fältskogand and Anni-Frid Lyngstad, and you get an unparalleled, euphoric listening experience.

In his New York Times op-ed about the song, Jeff Tweedy called ‘Dancing Queen’ ‘exuberantly sad,’ which I suppose refers to its bittersweet lyrics, often interpreted as a melancholic pining for one’s youth. But I’ve never seen it that way. The song is about getting lost in music and living entirely in the moment, at least in part because it’s Friday night and the lights are low. Studies of the human condition don’t get much more universal than that.

‘It’s often difficult to know what will be a hit,’ Fältskogand said later. ‘The exception was ‘Dancing Queen.’ We all knew it was going to be massive.’”*

Along with the Hot 100, “Dancing Queen” went to No. 1 in 12 different countries in 1977. It’s sold over 7 million records worldwide and has been played nearly as many times on American radio.

17. “Dreams” by Fleetwood Mac (1977)

Two chords. A Rhodes piano. Pure pop-rock perfection.

Written quickly in an unused room at the Record Plant in Sausalito. “Dreams” is Stevie Nicks’ finest contribution to Rumours, the Fleetwood Mac blockbuster the band would spend the rest of their careers, together and separately, trying to replicate. The instrumental has a steady, almost tribal pulse that gives the song an utterly hypnotic quality. That surehandedness ends up becoming the comforting emotional register the entire song lives in.

Here’s some more of my thoughts on the song, courtesy of my Fleetwood Mac “best of” deep dive:

*Nicks wrote it in 10 minutes with a drum loop and a Rhodes piano pattern that came tumbling out of her […] When she presented the song to the band, they were less than enthused. Christine McVie, who [thought] it was simple to the point of being boring. But, at Nicks’s insistence, a basic demo track was recorded the next day, with Nicks playing the piano and singing. Those elements made it onto the final cut of “Dreams” with minimal editing, even after she recorded nearly a dozen takes of the lead vocal.

This track has also benefited from several social media resurgences, most notably Nathan Apodaca’s viral TikTok video from 2020. On top of inviting a slew of parodies, including from Mick Fleetwood himself, the moment catapulted the song back into the mainstream conversation, re-entering the Hot 100 at No. 21, more than 40 years after its initial release. Even if you had no concept of Fleetwood Mac or* Rumours prior to that viral moment, it’s an easy track to fall in love with for the first time.

Out of four singles, all of which cracked the Top 10 of the Hot 100, “Dreams” was the only No. 1 off Rumours, peaking in June 1977.

18. “Kiss You All Over” by Exile (1978)

Fans of Sweet and Suzi Quatro, just to name a couple, will recognize the names Mike Chapman and Nicky Chinn. For those who aren’t familiar, the duo built hits for those and a handful of other glam-adjacent acts before “Kiss You All Over” ever materialized. It’s odd to parse out the rationale for the two men handing these incredibly horny lyrics to a Kentucky bar band named Exile. Their previous big swing at a pop hit, “Try It On,” had peaked at No. 97 on the Hot 100. A couple of personnel changes later, the group spent an entire day recording their parts for this track, due to what has been described as Chapman’s “demanding” production style. I’d say it paid off.

Like any good bit of foreplay, “Kiss You All Over” succeeds because it takes its time with its sonic seduction. The bass line is patient and gentle in its thump, the synths shimmer with carnal intrigue, and J.P. Pennington’s lead vocal (his first-ever for the band) is as breathy as it is unambiguous. Even amid crossover hits that were becoming more and more sex-forward, this track stands out as one of the steamiest. It’s engineered with single-minded intent and, for those who find it appealing, it works without objection.

“Kiss You All Over” stayed at No. 1 for four weeks in 1978, outlasting the Bee Gees, Andy Gibb, and the entire Grease soundtrack in that top spot during what was one of the more competitive chart years of the decade (maybe of all time). Exile pivoted to country music in the 1980s and found its footing there, making its career trajectory one of the era’s strangest. “Kiss You All Over” outlasted their country catalog partly because Chapman and Chinn built it to last and partly because the song doesn’t ask you for more than it needs. It does what it says on the tin.

19. “Heart of Glass” by Blondie (1979)

Blondie was a CBGB band. They came up alongside the Ramones, Television, and Talking Heads, and, only a few years into their career, releasing a disco single was, in the eyes of the punk establishment, tantamount to an act of treason. But co-founders Debbie Harry and Chris Stein didn’t care. They’d always been more interested in pop as a concept than as an act of puritanical genre loyalty, and “Heart of Glass” was the commercial proof their instinct was on the money.

The original version of the song existed in a slower, more reggae-influenced form as early as 1975. Back then, it was called “Once I Had a Love.” Producer Mike Chapman, the same Chapman behind “Kiss You All Over,” heard something in the structure during the Parallel Lines sessions and pushed it into disco territory. The transformation required a Roland CR-78 drum machine, a warmer synth bed, and Harry’s ice-cold, detached vocal floating above all that machinery. The backlash from their punk-forward base was swift and teeth-gnashingly intense, but so too were the sales. “Heart of Glass” held the No. 1 spot on the Billboard Hot 100 for one week, helping push the parent album to Platinum-level sales in the US. The song also topped the charts in the UK and across Europe.

What’s more fascinating is the before and after inflection of “Heart of Glass.” All of a sudden, a band known primarily for its snarling riffs and galloping rhythm section had a diverse, more intricate sonic repertoire. They’d still put out rock material after this song, but I don’t think the doors open for subsequent hits like “Call Me,” “The Tide Is High,” and “Rapture” without this track clearing the path first. The arrangement also sounds so modern, nearly a half-century after it first hit store shelves and radio airwaves. Who knew detachment could be this transcendent?

20. “Don’t Stop ‘Til You Get Enough” by Michael Jackson (1979)

Let’s close this list with the King of Pop’s Hot 100 origin story as a solo artist.

When Michael Jackson dropped Off the Wall, the disco-funk masterpiece that would go on to sell 20 million copies worldwide, he was just shy of his 21st birthday. He’d been famous since he was 11 as the face of his family’s band, the Jackson 5. But, as that vehicle’s momentum began to wane in the second half of the 1970s, he spent several years searching for what he should do next. He found that creative springboard when he connected with producer exrtaordinaire Quincy Jones on the set of The Wiz in 1978. The two instantly clicked and formed one of the most important musical partnerships in pop music history.

“Don’t Stop ‘Til You Get Enough” was the lead single from Off the Wall, their first collaboration on a studio album. Jackson has a co-production credit in addition to one for songwriting, and it’s perfectly suited to his sensibilities as a performer. The spoken-word intro, breathy and nervous and giddy, flutters over a throbbing baseline. That combination immediately sets the tone and puts you on alert until, a few seconds later, the strings rush in and the groove absolutely detonates. The track technically qualifies as disco, but there’s so much more going on that simply labeling it as such would be reductive. The bass line, the horn arrangement, the vocal doing things in the upper register that shouldn’t be physically possible—all perfection.

So perfect, in fact, that it didn’t sound like anything else on the charts in 1979. It officially set the Michael-Jackson-as-pop-savior complex in motion. “Don’t Stop ‘Til You Get Enough” held the top spot for one week, fueling Off the Wall’s rise to No. 3 on the Billboard 200. That LP was a runaway train after that, producing four Top 10 singles but failing to win the Grammy for Album of the Year. Jackson was reportedly furious, and that slight reportedly fueled the ambition behind Thriller.

Talk about a positive run-off effect.

Which 1970s No. 1 would you have added? And which one on this list are you putting on right now?

The Billboard Hot 100 launched in August 1958 as an attempt to settle a debate: Which songs were actually connecting with American audiences?

That meant canvassing reported sales from record stores, jukebox plays, and radio airtime and combining them into a single definitive ranking of the most popular music in America. On August 4, the company crowned its first-ever No. 1, “Poor Little Fool” by Ricky Nelson.

Many decades and changes to the media landscape later, the Hot 100 is still going strong. As of the week ending May 30, 2026, the chart has had 1,192 No. 1 entries, many of which have become some of the most recognizable songs in pop history. In this edition of my Summer of Billboard series, I’m covering the Hot 100’s first full decade, the 1960s.

Though perhaps best known for the British Invasion and Motown, this list covers much more ground than that. It’s my personal Top 20 from that decade, not the 20 “objectively most important” songs that topped the Hot 100 between 1960 and 1969. I’m sure some of these will be seen as consensus picks, and a few of them I’ve already covered in this newsletter.

That said, I did my best not to turn this and other lists in this series into a tired cliche. We’ll see if that holds. My only rule, aside from the requirement that all the songs had to be No. 1s, was that I limit myself to one song per artist. So you’ll only see one entry from the Beatles, the Supremes, and so on.

If you’re a paid subscriber and want access to the companion playlist of my 100 favorite recordings from the 1960s (irrespective of chart position), keep scrolling or click the next button. If you’re not a paid subscriber, it’s an excellent moment to consider an upgrade if you can.

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In chronological order, let’s begin:

1. “Save the Last Dance for Me” by The Drifters (1960)

According to Doc Pomus, “Save the Last Dance for Me” was almost forgotten before it ever had a chance to be something. Atlantic originally told him and Mort Shuman, his songwriting partner, that the track was first relegated to a B-side. It wasn’t until Dick Clark got a hold of the single that he turned it over and quickly realized that this R&B classic was, in fact, the better of the two songs.

The story behind the lyrics is a bit of a sad one. Lou Reed, who worked with Pomus on other material, told the story that the scribe supposedly came up with the words while watching his wife dance with other men at his own wedding reception. Pomus had polio as a child and was either wheelchair-bound or on crutches for much of his life. That he turned such specific personal grief into one of the most emotionally charged pop singles of the decade is quite a feat on its own.

And then there’s the actual music, which is lush and warm and deftly orchestrated, like a lot of Atlantic records from that period. Featuring Ben E. King on vocals, “Save the Last Dance for Me” held the No. 1 spot on the Hot 100 for three weeks in October 1960. It also topped the R&B chart simultaneously.

2. “Georgia on My Mind” by Ray Charles (1960)

Ray Charles’ recording of the Hoagy Carmichael-Stuart Gorrell standard is, without a doubt, one of the most beautiful songs I’ve ever heard.

The way those strings, aching with so much longing and nostalgia, float in to immediately set the tone is unforgettable, as is when the lower end of the arrangement comes in a half-second before his voice does. As he did with much of his greatest hits, Charles brought in a distinctive blend of gospel and blues, turning a wistful slice of Tin Pan Alley into something that comes across as far more confessional. His vocal take is not only his best, but one of the most moving ever committed to tape.

“Georgia on My Mind” hit No. 1 on the Hot 100 in November 1960 and won Charles two Grammys the following year, including Best Male Vocal Performance. In 1979, the Georgia state legislature voted to make it the official state song, and Charles performed it at the state capitol for the occasion. That full-circle, boundary-smashing moment tells you something about how thoroughly it replaced every other version in public memory. Is there a truer mark of genius?

3. “Will You Love Me Tomorrow” by The Shirelles (1961)

Beginning with this song, this list will reveal one of my soft spots as a music nerd: 1960s girl groups.

From the harmonies to the slyly subversive lyrics to the outfits showcased on various television appearances throughout their rise to prominence, there’s something about them that I will always adore. Before I move into the thick of the Motown ascendence, it’s important to acknowledge one of the subgenre’s first success stories, the Shirelles, through their No. 1 hit, “Will You Love Me Tomorrow.”

Written by Carole King and Gerry Goffin and initially conceived of as a country number, it was a trailblazing first, becoming the first recording by a Black female group to reach No. 1 on the Hot 100. The song asked, in language polite enough for Top 40 radio and specific enough to make several stations ban it anyway, whether the desire a girl feels tonight will be answered with respect in the morning.

The approach was more direct than mainstream pop permitted for women at that time, and Luther Dixon’s detailed production gave their words a vulnerability that felt elegant rather than exposed or used. It set the template for the Brill Building ballad for years to come.

4. “Blue Velvet” by Bobby Vinton (1963)

Let’s put aside the irony and icy remove of this song’s legacy in the titular David Lynch film for a moment and take it at face value.

The sweetness of Bobby Vinton’s “Blue Velvet” is totally disarming. It’s an airy, innocent tale of love, written in 1950 by Bernie Wayne after he’d caught multiple glimpses of a woman at a party clad in a dress made of the eponymous material. The song had previously been a success for Tony Bennett as well, who’d scored a Top 20 hit out of it in 1951. But Vinton’s released, which topped the Hot 100 for three weeks in September 1963, has become the de facto version of this standard.

That was the song’s first life, anyway. Its second one came more than two decades later, Lynch used it as the title and musical centerpiece of the aforementioned 1986 cult classic. The director understood that the song’s sugary surface masked something darker underneath, a nostalgia so perfect it turns unreal, perfectly concealing the rot by being more beautiful than anything you’d expect to find in its vicinity. The record definitely has it both ways.

5. “She Loves You” by The Beatles (1963)

Okay, the Beatles song.

Not necessarily the one that gets cited as the most “important” Beatles song of that era, but undeniably their most commercially successful, especially in the UK. “She Loves You” set multiple sales records after it was released, eventually becoming the Fab Four’s best-selling single in their home country, as well as the top-selling record in Britain in the 1960s. In the US, it was one of the songs that helped the band hold down all Top 5 spots on the Hot 100 the week of April 4, 1964.

All that pomp and circumstance aside, it’s a simple, pretty, energetic pop song. According to McCartney, the song’s conceit elaborated on the call-and-response structure of Bobby Rydell’s “Forget Him.” The “yeah yeah yeah” rejoinder is what makes his and Lennon’s spin on it work, serving as this delightful outburst of affirmation that has gone down as one of the most memorable pop or rock hooks of all time.

“She Loves You” captures the pre-Rubber Soul Beatles at their most compressed and euphoric, a band that understood Beatlemania was exploding around them, one detonating chorus after another.

6. “I Get Around” by The Beach Boys (1964)

The fact that the Beach Boys hit the top of the Hot 100 chart for the first time on July 4, 1964, carries a whole lot of extra meaning if you’re paying attention to the timeline.

Prior to that date, the British Invasion had irreversibly reshaped American radio with the kind of pop music no one had heard before. Fairly or not, “I Get Around” was seen as a homegrown counterpoint to the Beatles and their cultural movement brethren, complete with vocal harmonies so dense they still make the air feel thicker around you, and a falsetto lift in the chorus that has become a sonic hallmark all its own.

Brian Wilson and Mike Love wrote it against the backdrop of their group’s newfound fame and, as so often happens when you find success in the music business, increasing competition. Wilson’s arranging instincts, though not quite at Pet Sounds levels just yet, were already operating at a level that separated him from his peers. Even in a breezy song like this, which is about cars and weekend plans, you can already hear the studio thinking that would eventually produce game-changing pop a few years later.

7. “Oh, Pretty Woman” by Roy Orbison (1964)

What 1960s Hot 100 reminiscence would be complete without Roy Orbison?

Even though I’m on record as having a soft spot for late-period Orbison, “Oh, Pretty Woman” is arguably (and by that I mean probably) his best, most enduring pop single. Interestingly (and I wasn’t aware of this fact before researching this Billboard series), this song was only his second Hot 100 No. 1, the other being “Running Scared,” and ultimately his last chart-topper in the US. A couple of his other greatest hits, “Crying” and “Only the Lonely (Know How I Feel),” stalled out at No. 2.

That world-famous opening guitar figure came from session player Billy Sanford, who stumbled into one of the most recognized riffs of the decade. Orbison heard it, knew what it was immediately, and built a song around it. The title came from a conversation with his wife Claudette, who was heading out and, after Orbison asked if she needed any cash, co-writer Bill Dees interjected that “a pretty woman never needs any money.“

The record held No. 1 for three weeks starting in September 1964 and eventually sold an incredible 7 million copies, making it the commercial apex of Orbison’s career.

8. “The Game of Love” by Wayne Fontana and the Mindbenders (1965)

In a notable reversal of what the chart trends were during the first half of the 1960s, Wayne Fontana & the Mindbenders’ “The Game of Love” failed to reach No. 1 in Britain (it stalled at No. 2) but got over that hump and ascended to the top of the Hot 100 in early 1965.

Prior to the single’s release, Wayne Fontana and his band were barely a household name outside England. But, buoyed by lyrics from Clint Ballard Jr., who’d go on to write another chart-topping hit that will be covered later in this series, the group suddenly had a surefire smash on their hands. At a time when pop artists were crafting songs with an increasing social conscience, this track is a bright, breezy balm. It’s a short burst of upbeat, maybe slightly smug, beat pop.

Wayne Fontana and the Mindbenders burned bright for a short period, but never really recaptured the level of fame they achieved with “The Game of Love.” The group sans Fontana would get close the following year, when their cover of “A Groovy Kind of Love” would peak at No. 2. Fontana’s biggest solo single, “Pamela, Pamela,” didn’t make a significant dent stateside, and he would later be beset with legal and financial issues. He died in 2020 at age 74.

9. “These Boots Are Made for Walkin’” by Nancy Sinatra (1966)

Written by Lee Hazelwood (initially for himself, which, considering the lyrics, is a bullet he was wise to dodge), “These Boots Are Made for Walkin’” is one of those songs that will live forever. I say that because, more than the performances and compositions, which are all top-notch, it’s a pop song that legitimately stands for something.

In my original review of the song for my Fun Song Friday series, I wrote:

“‘Boots’ has evolved into one of the most recognizable feminist anthems from the 60s. It’s a genuinely empowering song compared to almost-there chart-toppers who trafficked in the same subject matter like the Supremes’ “Stop! In the Name of Love.” In that essay, I wrote about how that song’s myopic portrait of a scorned woman “[stops] just shy of delivering ultimatums concerning bad behavior.” If Diana Ross and company knocked softly on feminism’s door, Nancy Sinatra kicked the whole thing in with relish.”

These days, the track is widely accepted as shorthand for 1960s female swagger, a big part of why it’s been sampled, covered, and interpolated so many times in the decades since. Leave it to Nancy Sinatra to take a man’s lyric about revenge and turn it into something women have been righteously claiming and reclaiming ever since.

10. “Strangers in the Night” by Frank Sinatra (1966)

For someone of Sinatra’s cultural stature, it’s difficult to believe that this song is his only solo single to hit No. 1 on the Hot 100. The only other time he got to the top of this US singles chart was with “Somethin’ Stupid,” his duet with eldest daughter Nancy, which stayed in the top spot for four weeks in 1967. If I have one shot to carve out space for Sinatra on this list, this track is an apt gateway, epitomizing the kind of dreamy, forlorn ballad that no one could pull off like Ol’ Blue Eyes.

The melody, composed by German orchestra leader Bert Kaempfert, was originally part of the soundtrack for the James Garner film A Man Could Get Killed. You can hear it multiple times in the score, including during the end credits. Does that make Sinatra the godfather of modern-day sampling, predating a lot of the Blaxploitation soundtracks that hip-hop producers would riff on years later? The parallels go deeper than that, by the way. Years later, there was a rights battle over the song’s authorship that was tied to a larger crime ring.

Whatever you call it, the melody was given English lyrics by Charles Singleton and Eddie Snyder, the record was cut in about an hour, and Sinatra’s comeback was in full swing shortly thereafter. Despite Sinatra openly disliking this song and mocking it onstage during live shows, it became his most enduring late-career success story. The eponymous album would eventually become a Platinum seller, and the song itself won Sinatra Grammys for Record of the Year and Best Male Pop Vocal Performance in 1967.

He’d continue to release quality material (That’s Life in 1966, My Way in 1969, and the slept-on Watertown in 1970), but, chart-wise, this one’s still his crowning achievement.

11. “Reach Out I’ll Be There” by Four Tops (1966)

Of all the songwriting teams who have dominated the Hot 100 during its existence, few have been as prolific or influential as Lamont Dozier and brothers Brian and Eddie Holland, better known as Holland-Dozier-Holland (HDH). In 1966 alone, the Motown legends wrote crossover hits for acts like the Isley Brothers, Kim Weston, the Supremes, Marvin Gaye, and the Four Tops. To peruse their songwriting credits is to steep your brain in pop and R&B excellence.

But, in the here and now, let’s focus on this Four Tops No. 1, which, according to Dozier, was influenced by Bob Dylan of all people. He and Eddie Holland wanted the lyrics to have an in-your-face quality to them, and they encouraged Four Tops lead vocalist Levi Stubbs to “shout-sing” his contributions as a sort of ode to Dylan. The result is an infectious, pretty bracing pop&B hybrid that has more than a wisp of rock in its DNA. The urgency in his voice and the session playing is palpable, which is really what elevates the track into pop’s forever pantheon.

The song hit No. 1, their second after “I Can’t Help Myself (Sugar Pie, Honey Bunch),” on the Hot 100. It also topped the US R&B chart and the UK singles chart in the last months of 1966. The Four Tops have a ton of legitimately great songs in their catalog and are worthy of their own deep dive in this newsletter one day. I recommend you (re)visit their greatest hits on your preferred physical media or streaming platform. If you’re looking for some great HDH stories, check out this podcast the brothers did with Nile Rodgers in 2024.

12. “You Keep Me Hangin’ On” by The Supremes (1966)

Let’s stay in the HDH for another list entry and use it as a gateway to discuss my favorite Motown group of all time, the Supremes.

Their run of commercial success of 12 Hot 100 No. 1s, beginning in 1964 with “Where Did Our Love Go” and “Baby Love,” has rarely been matched by the legions of imitators who count Diana Ross, Mary Wilson, and the rest of the rotating cast of performers as chief influences. They even got a smash-hit Broadway musical and film adaptation modeled on their backstory. The harmonies, the sultry style—it’s all still so perfect. They were easily the most challenging act to pare down the options to a single list entry for this post, but, in my heart of hearts, their most memorable song will always be “You Keep Me Hangin’ On.”

It starts with the choppy guitar figure you hear in the opening few seconds, a riff that drives the rest of the record. It’s like a desperate Morse code dispatch, signaling all is not well in the central relationship described in the lyrics. By building the entire arrangement around that staccato pattern, this track is one of the most rhythmically aggressive singles the Supremes ever released. The density of the multitracked guitars sounds amazing on a high-end hi-fi system, and that weary Diana Ross vocal introduces a note of anxiety that takes it to another level.

“You Keep Me Hangin’ On” was an important bridge point in the Motown discography, connecting the clean-cut soul of those earlier hits to the harder-edged funk that would define the label’s early 1970s output.

13. “Light My Fire” by The Doors (1967)

Founded in 1965 in Venice, California, the Doors are one of the more divisive names from the 1960s classic rock hit parade. They had a short-lived peak, lasting from 1966 through 1970, and had a tumultuous go of it in the studio. A major reason was “tortured genius” poster child Jim Morrison, a talented poet and raging alcoholic, who became better known for his off-stage antics than his contributions to the group’s musical output. Your mileage will vary on whether or not you think he’s still alive or not.

Contrary to what some outlets report, Jim Morrison didn’t write a significant portion of “Light My Fire.” Guitarist Robby Krieger wrote most of it, which might be why it’s one of the odder anomalies in the band’s repertoire, not to mention Hot 100 history. It’s long, at over seven minutes, and kind of baroque-sounding, with this winding, trippy organ solo in the middle. Initially, Elektra edited it for radio, cutting most of the extended instrumental passages, but the version you hear in most places now is the album cut. The disconnect between what the lyrics describe (lustful desire) and how they describe it (with funerary language like “pyre”) adds to the head-scratcher nature of its construction. It shouldn’t work, and yet somehow it does.

You could say the same for a lot of the Doors’ best-known work (see “People Are Strange,” “Alabama Song (Whiskey Bar),” and the LOL-inducing irony of Jim Morrison singing “Touch Me”). If you wound the clocks back and did the 60s over again, I’m not positive they hit as universal a nerve as they did. They weren’t really cut out for, or, depending on who you ask, desiring of, pop superstardom. The Ed Sullivan Show incident, where Morrison supposedly agreed to change the line, “Girl, we couldn’t get much higher,” before a broadcast performance of “Light My Fire,” only to renege at the last moment, should tell you all you need to know.

14. “Ode to Billie Joe” by Bobbie Gentry (1967)

“Ode to Billie Joe” is one of the greatest rope-a-dopes in pop music history.

The song starts out so unassuming and wistful, describing a Mississippi like any other, with cutting cotton and baling hay. Straight out of a Norman Rockwell painting. Then, out of nowhere, the narrator’s mother tells the family, matter-of-factly, that Billie Joe McAllister jumped off the Tallahatchie Bridge earlier that morning. The family keeps eating. The conversation nonchalantly shifts to the crops and other topics, all from the same flattened domestic point of view. The father, immediately after admonishing Billie Joe for not having “a lick of sense,” asks for biscuits.

That is how the song withholds what the listener most wants to know: who Billie Joe was to the narrator and what it means that he is gone. But the lyrics never give you that closure. Gentry, who, as of this writing, is still with us at age 83, has kept her silence for nearly 60 years. She also arranged the strings herself, an addition that was unusual at the time it was recorded but helps give the instrumental this deep sense of foreboding. It’s the most elegant of chillers, which is arguably why it spent four weeks at No. 1 on the Hot 100 in August and September 1967 in the first place.

“Ode to Billie Joe” ultimately finished third on Billboard’s year-end chart and won two Grammys the following year, for Best New Artist and Best Female Pop Vocal Performance.

15. “Respect” by Aretha Franklin (1967)

When I discussed this Aretha Franklin classic in my deep dive into her studio discography, I called it “a soul classic so beloved and ubiquitous that most people either don’t know or don’t acknowledge it as an Otis Redding cover.” Redding’s original version dates back to 1965, framed as a demand from a working man to his wife. He’s out there, grinding away, making sure ends meet, so show some appreciation when he gets home. It’s an assertion of domestic authority through a funk groove. Aretha’s take is something completely different.

Along with her sisters and producer Jerry Wexler, she reworked the arrangement and rebuilt the song’s emotional logic from the ground up. The instantly familiar “sock it to me” call-and-response gave the bridge much more insistence, and in her most decisive move, Franklin spelled out the title: R-E-S-P-E-C-T. That minor addition shifted the entire energy and focal point of the song. Where Redding had been asking a woman for deference, Franklin was demanding what she deserved.

The record topped both the Hot 100 and the R&B chart in 1967. It also won her two Grammys and global recognition as an activist voice that wouldn’t be silenced. Others who wanted to stand up for their needs and values followed suit, with the song being co-opted by civil rights leaders and feminist organizations alike. It’s the rarest of pop standards that has become an anthem for whichever marginalized group needs its support.

16. “(Sittin’ On) The Dock of the Bay” by Otis Redding (1968)

Otis Redding’s most famous song, the one that will still be covered and used as a needle drop in film and TV mini-series, was recorded just days before he passed away in December 1967, in the plane crash that claimed the lives of six other men besides his own. Redding was 26 when he died. In the months prior, he’d scribbled lyrics and ideas for the song down on napkins and hotel stationery. His co-writer on the track, Steve Cropper, [elaborated](”Guitarist, songwriter and producer Steve Cropper”) to NPR in 1990:

“[The] story that I got, he was renting a boathouse, or stayed at a boathouse or something, and that’s where he got the idea of the ships coming in the bay there. And that’s about all he had: “I watch the ships come in, and I watch them roll away again.” I just took that ... and I finished the lyrics. If you listen to the songs I collaborated on with Otis, most of the lyrics are about him […] “Dock of the Bay” was exactly that: ‘I left my home in Georgia, headed for the Frisco Bay’ was all about him going out to San Francisco to perform.”

Stax released the record posthumously in January 1968, and it became the first posthumous No. 1 single in the history of the Billboard Hot 100, holding the position for four weeks. Heavily inspired by the Beatles, the single points toward the superstar Redding was becoming. Sadly, we never got to see or hear what would’ve been.

17. “Everyday People” by Sly and the Family Stone (1969)

The most impressive part of “Everyday People” by Sly & the Family Stone is that it’s a protest song that doesn’t rankle the listener by turning up the volume (vocally, that is) from some sort of unseen pulpit. There’s no screaming, no fire-breathing manifesto. Instead, even though it arrived in late 1968, during one of the most turbulent sociopolitical stretches in American history, it chooses to speak its mind simply and plainly, and it’s a much better song as a result.

Sly and his group walked the walk, too. They were a racially and gender-integrated band at a time when that was a rarity, and they shrugged it off as something so commonplace that you needn’t mind. As the song tells us, “different strokes for different folks.” On an album, the exceptional Stand, that features a track titled “Don’t Call Me N*****, Whitey,” the rougher edges are sanded down here, painting a picture of a better world where we’re all a little bit nicer to one another.

It’s one of the most sampled records in funk and R&B history, and its influence has been spreading across decades, subgenres, and cultural movements for more than half a century. “I am no better, and neither are you,” Sly says at one point. “We are the same, whatever we do.” Amen to that.

18. “Aquarius / Let the Sunshine In” by The Fifth Dimension (1969)

I’ve never seen an iteration of the musical Hair, nor do I have a firm grasp on just how large its shadow looms over 1960s counterculture, but I’m told it’s a very, very big deal. I do, however, know that the Fifth Dimension, one of the decade’s most fascinating soul-rock hybrids, who are rightfully being reappraised following the Summer of Soul documentary, took a couple of the musical’s songs, cut a medley, and eventually spent six weeks at No. 1 on the Hot 100.

What I’ve always loved about this record is how tight, warm, and totally disarming it is. You’re thrust right into this cosmic mysticism, with the pulsing bass and drums underscoring the spiritual importance of the Age of Aquarius. When I first heard it as a kid (and I’m an Aquarius, key part of the story), I had no idea why they kept talking about Jupiter aligning with Mars and all that. As an adult, I recognize the thesis, “peace will guide the planets, and love will steer the stars.” That must’ve been a t-shirt slogan at one point.

“Aquarius” has become one of the most emblematic hits of the Hippie generation, winning the group their second Grammy in 1970 and nearly becoming the biggest song in the US in 1969 (the Archies’ “Sugar, Sugar” nabbed that honor). It’s also a good example of a trend I noticed when putting this list together—how quickly mainstream pop grafted onto material from subcultures in order to sell records. I wonder if that’s still going on …

19. “Honky Tonk Women” by The Rolling Stones (1969)

The Rolling Stones are the proud owners of eight Billboard Hot 100 No. 1 records, including well-known hits like “(I Can’t Get No) Satisfaction,” “Paint It Black,” and “Brown Sugar.” Even though I like most of their chart-toppers, I must respect the one-song rule and defer to what I think is sneakily the catchiest single they released in the 1960s, “Honky Tonk Woman.” Is it their best, most polished work? Probably not, but you’re unlikely to find a better time in their catalog from that period in the band’s history.

Mick Jagger and Keith Richards wrote this song while on holiday in rural Brazil of all places, first conceptualizing it as a straight country number called “Country Honk.” They recorded a demo of that version, and it’s supposedly the last sessions that Brian Jones participated in before his death. There are conflicting stories as to whether producer Jimmy Miller, who played the cowbell intro, or recent addition Mick Taylor, who influenced the final direction of the song we all know and love, but by the time it arrived as a non-album single in July 1969, it sounded like nothing the Stones had previously released.

“Honky Tonk Woman” reached No. 1 in both the US and the UK, spending four and five weeks at the top of each chart, respectively. It also served as a capstone to a chaotic, tragic year for the band. The single came out the same week as the Stones’ free concert at Hyde Park, which they put on two days after Jones died, and right as the band was completing my favorite album of theirs, Let It Bleed. An end of an era, if you will.

20. “Suspicious Minds” by Elvis Presley (1969)

Fittingly, we close this discussion of my favorite No. 1s from the 1960s with a nod to the King of Rock and Roll.

“Suspicious Minds” was written by Mark James, who made his bones as a staff songwriter for Memphis producer Chip Moman’s publishing company. He wrote hits including “Hooked on a Feeling,” which was first recorded by BJ Thomas, “The Eyes of a New York Woman,” and, after his collaboration with Elvis Presley, “Always On My Mind,” which has been covered by dozens of high-profile artists over the years. He won a Grammy for the latter thanks to Willie Nelson’s version.

James actually tracked a version of “Suspicious Minds” himself, which went nowhere commercially. Then Elvis cut it at American Sound Studio with Moman producing in January 1969, slowing the tempo and leaning into the emotional arc with so much zeal that the final performance is one of the most operatic Elvis ever committed to tape. The King’s version hit No. 1 on November 1, 1969, and was the last time he’d ever reach the top of the Hot 100. Buoyed by the success of the 1968 Comeback Special, it also serves as an unofficial epilogue to the decade’s arc. The doe-eyed naivety was gone, both from his career and from the American consciousness.

The decade ended with him sounding more human than he ever had before, and I think it was a sign of those times.

Which 1960s No. 1 would you have added? And which one on this list are you putting on right now?

Genre: New Wave, Synth-Pop, New Romantic

Label: EMI Records

Release Date: June 15, 1981

Vibe: 🕶️

👉 Click the GIF to stream the album on your favorite platform

We humans, we love categorizing culture, don’t we? Before we fully understand what a piece of art is or what it will mean to current and future generations, we’re quick to gin up a few easily accessible labels, slap them on the box, and, in short order, start pigeonholing the artist(s), fairly or not, into corners that, more than anything else, serve to put consumer minds at ease. It’s to our collective detriment, in the end. Does labeling a song, album, or discography rock, pop, or disco do the work justice? Where precisely do the lines separating new wave from post-punk from dance-pop begin and end? And most importantly, can these labels ever push the critical and cultural conversation forward, rather than limiting it to tropes and clichés? I ask these questions because, like a few other acts from the 1980s, Duran Duran are so much more than they’re typically made out to be. It’s only in the past few years, following their belated induction into the Rock and Roll Hall of Fame in 2022, that the discussion around their greatness has shifted significantly, reaching beyond those tired labels and towards a deeper understanding of how influential their music really is.

Formed in 1978 by childhood friends John Taylor (bass) and Nick Rhodes (keys and synths), alongside their schoolmate Stephen Duffy, who would go on to have a successful solo career in his own right, Druan Druan went through several lineup changes before they ever got noticed by a major label. Drummer Roger Taylor joined in 1979, and both guitarist Andy Taylor and vocalist Simon Le Bon came on board in the first few months of 1980. By the time that iteration of the band performed together for the first time, they were already the residents at Birmingham’s Rum Runner club, a venue that became a hub for the burgeoning New Romantic movement. Alongside a bevy of British acts that include (but aren’t limited to) Spandau Ballet, Ultravox, Heaven 17, Soft Cell, and ABC, Duran Duran was suddenly seen as one of the acts at the forefront of what was considered one of the most creatively fertile periods for UK pop since the 1960s. Duran Duran spent much of that summer writing and demoing original material, as well as gigging in London and surrounding areas. By the time the majors came calling, they had already either penned or recorded early versions of everything that would appear on Duran Duran.

It’s arguable that the band’s self-titled debut wouldn’t have had the initial success it enjoyed without newly minted EMI A&R man Dave Ambrose in their corner. While working in the label’s publishing department, he’d already brought hit acts like the Sex Pistols and Dexys Midnight Runners into the fold. He had a keen ear for emerging talent and, after traveling to Birmingham to see them perform live, he was instantly bullish on Duran Duran’s future. “People used to say to me, ‘Dave, why are you getting so excited about this band?’” he said in 2011. “But I was convinced they were going to be massive.” He was also the voice within the group’s inner circle who pushed for the outstanding “Planet Earth” to be the lead single off their debut album. “I brought Duran’s demo tape home. I was with my wife, Angie, and Rob Hallett, the band’s live agent, came round. We opened some wine and listened through all the tracks. And Angie and Rob ended up dancing around the room. And we all, individually of each other shouted for ‘Planet Earth’ […].”

What’s striking, listening back to Duran Duran, is how confident and fully-formed a debut it is. So often, bands at that stage of their careers are still assembling an identity from the most readily available parts. They try out poses, audition different sounds and tones, and any distinctive personality traits peek out through the venetians instead of kicking down the door and announcing themselves with full-throated enthusiasm. You certainly hear the influences here, with odes to everyone from David Bowie to Kraftwerk to Giorgio Moroder audible for anyone looking for them, but they never obscure the specific synthesis at the band’s core. John Taylor and Rhodes had spent the better part of three years absorbing the post-punk energy of the Midlands scene alongside the pop, disco, and funk that dominated the American charts into the early-80s in equal measure. The built-in taste barometer is critical, especially when starting out. Rum Runner owners Paul and Michael Berrow also shaped the overall aesthetic as they transitioned into becoming Duran Duran’s management team. Every move here sounds deliberate.

If there’s an MVP to single out on Duran Duran (though, even as I say that, I will add that all individual performances on this record range from good to excellent), it’s John Taylor on bass. He’s the glue that holds these grooves together and gives them this irresistable bottom end that dares you not to move to them. “Girls on Film,” the album’s commercial apex, would crumble if it didn’t have that bassline in its foundational architecture. Colin Thurston’s production, as it is throughout the tracklist, is clean and crisp, adding polish to the final mix without crowding out Le Bon’s vocals or any of the instrumentalists. That funky, straight-ahead strut would be borrowed by countless other new wave and rock acts who pined for chart success, bridging the gap between humid dance clubs and accessible pop that almost instantly had broad appeal. As with their bigger hits, Duran Duran also had MTV in their corner, where the music video for this track played early and often. There’s apparently a much more naked version of the video that the BBC didn’t take kindly to and banned from their airwaves, though that move ended up giving the group more facetime in the press and surely helped increase their record sales. Sex sells, even if you can’t see it.

Other highlights include “Careless Memories,” which ratchets up the tempo and paranoia in equal measure, and “Night Boat,” which sucks you in with this swirling synth line before hitting you with a rhythm that’s more dub than it is rock (Clash fans, stand up). Le Bon’s slightly menacing vocal inflection is also darkly compelling as an emotional register, one he excels at when he chooses to return to it. There’s also the aforementioned “Planet Earth,” which remains one of their very best songs. It opens with a tasty, stuttering synth figure before Roger Taylor’s pounding four-on-the-floor drums set expectations before Le Bon utters a syllable. The chorus, built for arenas the band hadn’t played yet, was an instinct that turned out to be prescient rather than presumptuous. The track peaked at No. 12 on the UK Singles Chart in February 1981, four months before the album’s release. Andy Taylor’s guitar, an aspect of the band’s early work that divides some corners of their fan base, may be the track’s most underappreciated element. It’s not showy, but it’s also far from passive patchwork.

Duran Duran peaked inside the Top 5 and spent 118 weeks on the UK album chart, granting the band instant notoriety in their home country. It would later be certified Platinum and, in fits and starts, creep up the charts elsewhere in Europe. However, the New Romantic sound had yet to fully captivate American audiences, though that market wouldn’t deny Duran Duran for much longer. Their follow-up, Rio, was an even more impressive global smash, fueled by the lavish production value of the music video for the title track (it’s somehow sexy and hilarious at the same time) and “Hungry Like the Wolf.” They were one of the first acts that really understood the power of TV as a branding medium rather than a promotional afterthought. That said, the downside is that their persona, one wrapped in pastels and topped with impossible hair, began to overshadow their music. There are moments on albums like Seven and the Ragged Tiger and the much-maligned Notorious that I prefer to much of Rio, but they rarely get brought up in a more holistic conversation because all anyone remembers is the day-glo paint being poured onto those bikini-clad women lounging on the pier, beach, and boat.

It’s also worth mentioning how short-lived this specific iteration of Duran Duran was. Andy Taylor and Roger Taylor both left in 1985, and the band changed shape repeatedly across the decades that followed. They’re still recording and releasing underappreciated music to this day, with 2021’s Future Past earning a spot as one of my favorite LPs of the decade. But the version of Duran Duran that exists on this record—that specific combination of people in that specific moment of collective ambition, before the machinery of their own success closed in around them—was a finite thing. In that cultural flashpoint, they managed to construct the blueprint for what a ton of 80s new wave and pop-rock would sound like. Heavy on the synths and drums, precise in their melodies, and unrelenting in their pursuit of a hook that even the most cynical music fan would have a hard time resisting.

Which Duran Duran song is your favorite? Share it in the comments.

Genre: Indie Rock, Post-Punk, Alternative Rock

Label: Rough Trade Records

Release Date: June 16, 1986

Vibe: 👸🪦

👉 Click the GIF to stream the album on your favorite platform

There’s a misconception about this newsletter I’ve picked up on through my interactions with readers and the Substack community lately, which is, when I choose to review an album, I do so because I adore it and listen to it on repeat. That’s definitely not the case. More than some subscribers may realize, I devote album review space to works other people cherish that a) I haven’t had meaningful interactions with to this point in my life, or b) I’m compelled to give a second chance to. The Queen is Dead, an album that plenty of folks hold up as the paragon of 1980s indie rock excellence, falls into the latter category, and, to coincide with its 40th anniversary, the time was right to press play on this one again. I wasn’t so much turning over every stone I could find searching for greatness, but trying to dissect why it didn’t click with me when I first heard it as a teenager and early-twentysomething.

In general, I don’t dislike the Smiths. They’ve got some bops, both upbeat (see “This Charming Man,” a song that was a mainstay in a specific rock club I used to frequent with my wife when we first started dating … I have no idea if it’s still on the DJ’s shortlist of bangers to hit on a regular basis, but it wouldn’t surprise me if it still is) and dour (see “How Soon is Now,” whose instrumental still rattles through my car’s subwoofers semi-frequently). My primary objection to their hits and deep cuts in equal measure has always been that, to varying degrees, they try my patience. On Meat is Murder, for example, the activism in their lyrics comes across as more self-absorbed than anything else, particularly on cuts like the title track and “That Joke Isn’t Funny Anymore.” As danceable as some of the more uptempo tracks are, they also don’t really go anywhere melodically, an observation I’d extend to Morrissey’s vocals on most of the album. It’s not bad, just not something I vibe with. That sentiment used to sum up my relationship with The Queen is Dead, too.

But, on a fresh listen, this record started to take on a new life. I had this experience as a college film student with Francis Ford Coppola’s Apocalypse Now. The first time I saw it, I thought it was mostly ridiculous, saving the most egregious for last with the extended sacrificial allegory at Kurtz’s compound. Looking back on that reaction now, it’s a tad superficial or, at the very least, one-dimensional. What it lacks in self-control or self-awareness (neither of which is Coppola’s strength, anyway), it more than makes up for it with astonishing pyrotechnics and atmosphere. The Queen is Dead operates the same way. The grandiosity Morrissey brings to this record, the melodrama the band refuses to temper or apologize for, the dark humor that permeates every corner of the songwriting, it all reads as more than slightly obtuse the first time around. The fifth or sixth time? A stroke of near-genius.

The album is loud, arch, overreaching in spots, and completely uninterested in your objections, a disposition that makes it stick in your gut on repeated spins. Like Coppola’s film, what’s worth knowing is how close none of it came to existing at all. The Smiths recorded this LP in 1985 at RAK Studios in London while they were locked in an ugly standoff with Rough Trade Records over (what else?) money, in part due to the label’s own financial instability. The release was held up for months. On top of all that, Rough Trade founder Geoff Travis and the band were barely speaking (Morrissey threw a few lyrical jabs at Travis, most notably on “Frankly Mr. Shankly”). Guitarist and out-and-out rock legend Johnny Marr described The Queen is Dead sessions as the group’s creative peak, but one that carried a steep physical and psychological toll. His weight supposedly dropped to around 98 pounds as he ran on nervous energy and little else.

One of the underdiscussed aspects of this record’s legacy is how funny it is. Pitch-black comedy in a lot of cases, to be sure, but when you have Morrissey penning every song, it’s unlikely the messaging would be delivered in any other tone. Take the opening title track, which gallops through a gallows satire of the media’s obsession with the British royal family. Andy Rourke’s bassline is incredible, anchoring the storytelling in sly, deep-rooted cynicism. “I find as time goes by, this happiness we had slowly slips away and is replaced by something that is wholly grey and wholly saddening,” Morrissey told NME in 1986. “The very idea of the monarchy and the Queen of England is being reinforced and made to seem more useful than it really is. The whole thing seems like a joke. A hideous joke.” That last notion of a truth so ugly it can only make you laugh seeps into other songs on this album, including “I Know It’s Over” and “Cemetery Gates,” which serves up a wonderfully offbeat sonic contradiction. The jangle-pop guitar work and the buoyant drum pattern from Mike Joyce turn what could’ve been an ultra-bleak walk among the tombstones into something more of a jaunt. It’s as unnerving as it is transfixing.

For my money, the second side of this LP is where it truly earns its greatness. “Bigmouth Strikes Again” is a knowing wink at Morrissey’s proclivity for running his mouth in public, and while I’ve always found the songwriting amusing, I can never be sure how seriously or not he’s taking himself here. “I was only joking when I said I’d like to smash every tooth in your head,” he says early on. “Now I know how Joan of Arc felt/As the flames rose to her Roman nose/And her Walkman started to melt,” he adds later. It’s a surreal visual, picturing Maria Falconetti getting a few final tunes in at the stake. The excellent “The Boy with the Thorn in His Side” is a pot shot at the music industry’s “murderous desire” vis-à-vis their most commercial brands, and “There is a Light That Never Goes Out” is as sacred a text in the UK’s 1980s pop canon as you’re likely to find. Again, here you have an anthem that carries completely different meanings for different generations of fans. Some see it as a depressive excavation, while others have reframed it as a hopeful testament to love. It all depends on how you look through the kaleidoscope’s viewfinder.

The Queen is Dead peaked at No. 2 on the UK Albums Chart, held out of the top spot by Madonna’s True Blue, charted for 35 weeks, and has sold several million copies worldwide. In the US, it peaked at number 70 on the Billboard 200, an outcome that the band partly brought on themselves by refusing to license their music for advertisements and keeping American commercial radio at arm’s length. Arriving in the Summer of 1986, amid an ocean of manicured dance-pop on either side of the Atlantic, this material struck a much different chord, particualrly with critics. It was called by some as “the most realistic portrayal of England” of its era, which is a damning statement in several ways. The British mindset of the mid-to-late-80s was certainly before my time, but the more I immerse myself in the literature, the more shocking the political and cultural twists and turns become. While it was being recorded, this album apparently had the working title “Margaret on the Guillotine,” which should tell you everything you need to know about their collective political leanings.

The Smiths would never build on the momentum they generated with The Queen is Dead. Interpersonal tensions and growing media scrutiny led to the group’s dissolution in 1987, with Strangeways, Here We Come serving as their Let It Be, a more subtle and refined studio effort than maybe anything they’ve ever released, and yet I feel unsatisfied. There should be more to the story, no? As a body of work, their four studio albums leaves so much potential unrealized. When they were at the top of their game, as a unit and individuals, few Brit rock outfits wrote songs that became as universally beloved as theirs. A decent comp from the next decade would be Oasis, who similarly left their fans wanting more after they stopped recording together. Does that make me a hater? Or merely someone who wants to see the best of the Smiths, one final statement that we never had the pleasure of hearing? Reader, meet kaleidoscope.

What Smiths song has stood the test of time for you? Shout it out in the comments.

Commercially, the album’s ubiquity is unrivaled. It has sold over 5 million copies in the United States alone and has never been out of print since 1959. Even the most casual fans, folks who may only know Davis and a couple of other jazz names to begin with, are more likely to have this record in their collection than any of his other works.

But none of those measures vault it into the inner circle of the most important music he ever released. When Kind of Blue is both the beginning and end of a Miles Davis conversation, it crowds out a handful of records that genuinely changed how music was conceived, arranged, and recorded in ways that Kind of Blue, for all its beauty, didn’t.

This list isn’t meant to be a takedown. Kind of Blue is a great album. The modal improvisation, especially between Bill Evans, John Coltrane, and Cannonball Adderley, is everything people say it is. But Davis released 48 studio albums and reinvented his own sound at least six times. What follows are the LPs that shook the foundations of musical tradition and experimentation the world over.

Before I dive in, a quick reminder to do all the things, including subscribing and sharing this post if you’re enjoying this newsletter’s content so far.

In chronological order, let’s begin:

1. Birth of the Cool (1957)

This album is arguably the most important contribution Miles Davis ever made to the art form. True to its namesake, it popularized the “cool jazz” archetype, adding this detached, effortlessly elegant temperature to bop’s supple sonic curves. It’s the style that would define Miles’s career from that point forward and was, at the time, his most orchestrally ambitious work. He was all of 22 years old when he assembled the nine-piece band, including musicians like Gerry Mulligan, Lee Konitz, and J.J. Johnson, that would change jazz forever in three sessions, recorded in 1949 and 1950.

Amid all that starpower, the biggest influence on this record (and, to a degree, Davis’s trajectory as a musical tastemaker) was arranger Gil Evans, the Canadian orchestrator who had gained a reputation for crafting arrangements that were seen as punishment by other big band leaders. The two men would go on to release a handful of other jazz masterpieces in their time working together, such as Miles Ahead (1957), Porgy and Bess (1958), and Sketches of Spain (1960). Birth of the Cool would go on to influence multiple generations of West Coast jazz artists, as well as bossa nova greats João Gilberto and Tom Jobim.

If you’re looking for the moment when Miles Davis became a superstar, give this one a spin.

2. Milestones (1958)

A credit I’ve seen falsely attributed to Kind of Blue in various critical and academic writing is how it “invented” modal jazz. Compositions that fall into that category feature solos and band member interplay improvised over scales, rather than chord changes, the latter of which was the dominant way to go about your business as a jazz pro in the mid—to-late-1950s. The theoretical framework for this movement drew in part on pianist and composer George Russell’s book, The Lydian Chromatic Concept of Tonal Organization, a text Miles had been studying with keen interest.

On the title track for Milestones, Miles translated Russell’s experiments into a conceptual breakthrough that quickly became the organizing principle behind much of his music. No matter how many times I hear it, it’s never less than exhilarating in its interplay. The rest of the record is far closer to hard bop stylistically, with fearless contributions from an all-star cast that includes John Coltrane and Cannonball Adderley on saxophone, Paul Chambers on bass, and “Philly Joe” Jones on drums. “Dr. Jekyll” is one of my sleeper picks for best Miles Davis track ever, and “Two Bass Hit” is one of the brightest, most energetic tunes of its era.

On the right day, in the right mood, you wouldn’t have to twist my arm too hard to get me to say that I prefer Milestones to Kind of Blue.

3. Filles de Kilimanjaro (1968)

Often dismissed as a “bridge” album between the Second Great Quintet and Miles’s electric period, Filles de Kilimanjaro has evolved into one of the most underrated gems in the jazz impresario’s catalog. As important as the handoff moment is to his narrative, it obscures just how impressive the playing is top to bottom.

Miles recorded it in two sessions, five months apart, and the personnel’s pedigree is off the charts. The June session features Herbie Hancock, Wayne Shorter, Ron Carter, and Tony Williams, while the September session saw Chick Corea step in for Hancock and Dave Holland for Carter. The former’s dynamic on the electric piano is among the album’s most arresting elements, with the instrument becoming increasingly central as you roll through the tracklist. Corea leaves more room than Hancock does and also pushes harder rhythmically. The architecture is still mostly familiar from the Second Quintet days, but the walls were already expanding out to more experimental horizons.

Of all the compositions on this LP, “Mademoiselle Mabry” is the most prominent hinge moment. Betty Mabry, Miles’s flame at the time, had introduced him to the funk and rock records reshaping popular music in 1968, and the track named for her is the clearest evidence of the shift that was on the precipice of taking over his musical thinking: a groove-first sensibility that jazz tradition had no framework for. All the effects-drenched weirdness has yet to rear its head sonically, but the altered mindset was locking into place. If nothing else, this record is indispensable if you want a comprehensive understanding of Miles’s genius.

4. In a Silent Way (1969)

In a Silent Way is, in a word, perfection.

Recorded in a single day in February 1969, the final credits list boasts more than a dozen musicians “going electric” in ways that blur previously well-defined genre lines between jazz, rock, funk, and the bones of what would become ambient electronic soundscapes of the 1970s. Producer Teo Macero waved his magic wand in post-production, turning studio technology into a force that shaped performances and created a pervasive atmosphere of transfixing mystery. The approach was radical, altering how artists, producers, engineers, and labels conceived of how jazz records could be put together. It’s a powerful before/after inflection point.

The balance Miles and company strike here between richly textured, busy compositions that never feel chaotic or messy is astounding. Part of that is achieved through the instrumentalists’ contributions, but an equally important aspect of this album is the negative space between the notes that invites you to get lost in its delightful web of musical intrigue. The first side, “Shhh/Peaceful,” tacitly avoids any resolution, with wave after wave of electric piano and guitar drifting over Tony Williams’ glittering hi-hat. “In a Silent Way/It’s About That Time” is even more dazzling, featuring playing that’s so precise and unhurried that you can’t help but be drawn in. Joe Zawinul’s intro section is among my favorite stretches of jazz music ever.

As I often say when recommending legitimate 10/10 albums, I envy your first spin of this classic if you’ve never given it any play.

5. Bitches Brew (1970)

If In a Silent Way doesn’t split your skull open with its disregard for the “rules” of jazz as dictated by tradition, then Bitches Brew might blow it clean off.

The experimental apex of Miles Davis’s illustrious career, it’s an intense, bewildering, and, for some casual listeners, intimidating in its fusion-forward dissonance. And yet, in my original review of the album, I go over how many familiar influences Miles and his collaborators, particularly guitarist John McLaughlin, let bubble to the surface. Listen closely, and you’ll hear wisps of Ritchie Blackmore, Jimi Hendrix, Sly Stone, James Brown, and many other non-jazz entities helping this group push the art form into another sonic dimension.

I’ll let that initial write-up fill in some of the contextual blanks around what makes this release a must-listen, especially if you appreciate genius that can’t be defined in straight, neat lines. To that end, how you listen to Bitches Brew is also likely to impact your experience, regardless of whether you’re a first-time listener or not.

Here’s my recommendation:

“[I] want to add this disclaimer: If you’ve never listened to Bitches Brew all the way through, do yourself a favor and get your hands on the highest-quality speakers or headphones you can manage. You want the sound to wash over you from all sides, just as the recording intended. You want your listening experience to be as immersive as possible. And please, for the love of all things sacred in music, don’t you dare listen to this one from a smartphone speaker. That would be an insult.“

6. On the Corner (1972)

Of all the anarchic left turns in Miles Davis’s discography, On the Corner may be his most deliberately confrontational. Miles wanted to reach Black audiences who had moved from jazz to funk and soul, so he ended up making the most abstract, audacious science experiment of his career. There are no chord changes to speak of in the conventional sense, no solos in a similar vein. Practically nothing jazz purists from his existing audience would have recognized. Tabla, sitar, wah-wah trumpet, and layered percussion crashing into one another. It’s a doomsday scene for some, but it’s also a lot of fun.

As you might expect, critics hated On the Corner when Columbia first released it in 1972. It failed commercially, an outcome Miles later attributed to the label’s lack of a coherent marketing push. He said that, essentially, they didn’t want to back it 100% because they didn’t understand it. Whatever the case, Black audiences didn’t embrace it, and his jazz supporters rejected it as “selling out.” And yet, more than three decades on, legendary producers like J Dilla, Madlib, and Flying Lotus have cited it in their own work, confirming the record’s enduring appeal. It’s not hard to see why, too. Many of the arrangements and post-production choices anticipate hip-hop, R&B, and dance music production of the 80s and 90s in ways that are hard to dismiss once you hear them.

7. Get Up With It (1974)

You won’t find many 50-plus-year-old jazz fusion records that sound like they could’ve been made last year or even last week, but Get Up With It is one such release. A double album compiled from sessions that occurred between 1970 and 1974, it’s a wildly uneven and darkly compelling listening experience that, if you go into it with no inhibitions, will push all of the right emotional buttons. in exactly the right ways. The whole thing resists any concise sonic description, largely disregarding melody in favor of organ drone, wah-wah effects, and nerve-jangling rhythms. Miles’s health was deteriorating by this point, and after its completion, he nearly left the music business entirely.

Some more color, from my full review of the album:

“After Get Up With It, Miles Davis disappeared from show business. In his autobiography, he wrote of rampant substance abuse and promiscuity, habits that formed more as physical and emotional pain relief than anything else. “Sex and drugs took the place music had occupied in my life,” he observed frankly. Part of me wonders if this record took so much out of him that he needed years to recover and rekindle his love of the art form. By pushing the boundaries of what jazz, rock, funk, R&B, electronic, and various other genres could sound like, he’d also pushed himself far past the limits of what most musicians and composers would deem attainable. But that was Davis’ modus operandi until he passed away—to dig deeper. To look ahead to the future and what was possible instead of continuously dredging up the past and reheating well-worn trends or habits.”

From his 32-minute ode to Duke Ellington (“He Loved Him Madly”) to his equally epic Afrofuturist tornado (“Calypso Frelimo”), there’s over two hours of awe-inspiring material to sink your teeth into. It’s one of the strangest yet most unforgettable records you’ll ever hear.

Which Miles Davis has left the biggest impression on you? Let us know in the comments.

Genre: Hip-Hop, Gangsta Rap

Label: Roc-A-Fella

Release Date: June 25, 1996

Vibe: 🚬🎩

👉 Click the GIF to stream the album on your favorite platform

As a branding exercise, one that kickstarted one of the most profitable and reliable brands in rap history, Jay-Z’s Reasonable Doubt knows few equals. The man born Shawn Carter had been plying his trade as a sometimes emcee for several years prior, but had been consistently relegated to the margins of the music industry. He toured with Big Daddy Kane, rubbed shoulders with the Wu-Tang on the posse cut “Show & Prove,” and even sold tapes out of his car for a while with Damon Dash. Nothing stuck. Similar to Biggie Smalls’s origin story, Jay “made ends meet” (and by that I mean accumulated the piles of cash he’d need for his next major move) by dealing drugs in New York. Even with that financial safety net, he did what most would consider unthinkable, spurning contract offers from the likes of Def Jam to start the Roc-A-Fella label. In 2005, after the parent company bought half of his imprint for $10 million, Jay-Z became Def Jam’s CEO. As it turns out, there are perks to owning the incredibly successful company you rap for.

Now, I don’t think Roc-A-Fella existed (at first, anyway) because Jay-Z was such a staunch independent. It came to be because, back then, nobody took him seriously enough to give him the platform he thought his talents deserved. because nobody would sign him. In 1995, Payday Records had taken him on for singles, but they weren’t pulling their weight. “[They] were acting shady the whole time, like they didn’t know how to work a record or something,” Jay-Z said in 1999. “The things that they were setting up for me, I could have done myself. They had me traveling places to do in-stores, and my product wasn’t even available in the store.” So he, Damon Dash, and Kareem Burke pooled what they had, made a distribution deal with Priority Records, and built something from a position of total institutional rejection. The label’s name was even a classic Hova double entendre: rocking a fellow rapper and Rockefeller.

That tension, between where Jay came from and where he was about to go, is fitting creative fuel for a man who, for as long as I’ve been following his career, has been so singleminded about curating his own legacy. This album started life with the working title Heir to the Throne, which tells you everything you need to know about what kind of statement Jay intended. It became Reasonable Doubt during the recording process, reportedly influenced by the OJ Simpson trial, which was reaching its conclusion while sessions were underway at D&D Studios in Manhattan. The original concept for this record wasn’t even the Scarface-adjacent parable that it became at first. Instead, it would’ve positioned Jay-Z as a rapper on trial for being the best in the game, facing off against a jury of critics and peers deliberating on whether he belonged. That framing got scrapped, but the hubris behind it (Jay was a world-weary 26 when this LP dropped) remained intact.

“Can’t Knock the Hustle” opens the album with gravitas and establishes the production philosophy before Jay raps a word. The beat is this uncanny mix of warmth and grit, wisely using the specific nostalgia of 80s soul music as a fulcrum. It places Jay’s street accounting inside a tradition that carries an inherent weight of Black aspiration and survival. Rapping about drug money over that kind of sample, instead of a more booming (some would say archetypal) East Coast groove, reframes the narrative from what fans were more used to hearing at the time. Hindsight shows that the distance between what those sounds evoke and what Jay is actually describing is an emotional register that so, so many other emcees have reached for (the majority of whom have stumbled and faceplanted in the process). It’s deceptively difficult and, to Jay’s credit, takes laser-like focus to appear effortless. Rinse and repeat on “Politics as Usual,” which runs the same logic at a lower temperature. The Stylistics sample gives him a bit more room to breathe, and he sounds completely unhurried here. It’s insanely impressive.

The rest of the album’s first half covers a lot of biopic-type ground in short order. “Dead Presidents II” takes cues from both Lonnie Liston Smith’s piano and a Nas vocal from Illmatic, a move that lit the fuse for a beef that culminated in not one, but two of the most devastating diss tracks of all time. That beef is worthy of another article one day, but for now, let’s just say that they don’t make them like that anymore. Public fueds don’t carry the kind of bone-deep weight as that one did. Millennials who bore witness at the time know what I’m talking about. Elsewhere, a man who’s worked with both legends, DJ Premier, brings some of the record’s best production to “D’evils,” with Jay deploying equally dizzying wordplay to illustrate what street money does to people and what it costs them. “22 Two’s” is a gimmick that you can’t help but rock with, built around 22 variations on “to,” “too,” and “two” in a single track, while the Isaac Hayes sample underneath “Can I Live” gives orchestral weight to as cinematic a script as Jay has ever spit.

The sentimental favorite of mine, however, will always be “Brooklyn’s Finest,” a song that has only grown in stature since 1996. Clark Kent not only produced the beat but also brought the Jedi-in-training and the master, the Notorious B.I.G., together in the studio. At the time, Biggie was arguably the biggest star in hip-hop, while Jay was still largely a local sensation, like the “Juicy” star had once been. They had not been in the same room before Kent arranged it. What came out in the recording is two titans performing at the same level lyrically, closing the gap between their respective real-world positions in the cultural hierarchy. Kent has said that watching Jay construct a verse from memory unsettled Biggie enough that he went paperless in the booth from then on. It’s a stunning showcase of the best who ever did it. A close second in the “favorite song” department is “Regrets,” the album’s most devastating track. Premier’s sparse piano loop holds the instrumental together still while Jay names names on death certificates. It’s both a reflection of and a refinement of the mafioso-rap framework that’s still widely circulated today.

For how revered it is several decades on, it’s kind of surreal to look back and see that Reasonable Doubt did good but not great business during its initial release lifecycle. It debuted at number 23 on the Billboard 200 and number three on the Top R&B/Hip-Hop Albums chart, eventually went Platinum, and charted for 18 weeks. And yet, compared to the 14 number-one albums and 25 Grammy wins that followed, those numbers are on the modest side of Jay-Z’s career ledger. The album also arrived in one of the most loaded years in hip-hop history. Tupac’s All Eyez on Me and Nas’s It Was Written are just two of the all-time classics that dropped in that 12-month span. Pac was shot three months later, in September 1996, and Biggie six months after that. In the blink of an eye, the golden era of rap music that had made this record possible ended within eighteen months, though older heads like myself have been clawing to get it back ever since. Jay’s 20th-anniversary concert in celebration of this LP sold out in 2 minutes. I suspect his forthcoming shows at Yankee Stadium will do just as well.

Everything that followed for him got bigger and bigger and bigger. Vol. 2, The Blueprint, The Black Album, and several others became the bricks that formed the wall around Jay-Z, insulating him enough to become, if not the genre’s most dedicated artist, undeniably its wealthiest (which, in some circles, is the same thing). As of this writing, he’s pushing 60 and, in several recent interviews, comes across as trying a little too hard to protect, or at least reinforce, that pesky legacy of his. In a lot of ways, records like Reasonable Doubt play like bargaining chips for him in some ongoing game of status signaling. They’re used to remind us how great he was, seemingly to offset increasing evidence of how decidedly not great he allegedly was, too. But, as I did with Michael Jackson not long ago, the talent and baggage, no matter how ugly, must be taken in stride, as both inform the art through the artist. Whatever Jay-Z is purported to be now, it doesn’t change the fact that Reasonable Doubt is a stone-cold classic, one made without institutional support. The Recording Academy, bless them, eventually caught up.

What Jay-Z track from this period still brings the heat? Shout it out in the comments.

Starting in June and running through August, I’m publishing a series called “The Summer of Billboard No. 1s,” where I’ll be selecting my 20 favorite songs that reached the top spot on the Hot 100, one decade at a time. There are tons of great singles from every era, but if it didn’t claw its way to No. 1 on the Billboard chart, it doesn’t qualify for consideration.

Also, I’m purposely designating these lists as my 20 favorites. Not the 20 most important in an objective sense, nor an arbitrary collection of “essentials,” because, let’s be honest, those types of lists have been done to death and mostly tread on similar ground. My 20 favorites, which turns out to be a harder and more brutally honest undertaking than it sounds, is where I landed. It feels right, and I’ve really enjoyed making these, piece by piece, over the past few months.

I hope you’ll enjoy them just as much.

For those not in the know or who need a bit of a refresher, the Hot 100 has been the definitive measure of American popular music since 1958. Its history, which is every bit as checkered as you might expect, is fascinating reading in its own right if you’re interested. But what’s worth underscoring for a second is the American distinction there, one I didn’t make clear at the outset in my article about one-hit wonders and, predictably, got roasted for it. The UK singles chart will tell a different story of a decade’s hits, as will the equivalent chart in Canada, where I grew up. Keep that in mind when these start rolling out.

Overall, I’m sure some picks will surprise you (though maybe not, especially for subscribers who have been with me since the beginning), and others you may have forgotten even reached No. 1. I’m most interested in the songs that changed how I listen to music, the ones that land differently now that I’m closer to 40 than not. Hindsight and nostalgia make strange bedfellows, and I’ll leave it there for now.

Extra content for paid subscribers

Each post in the series will include an exclusive playlist: my favorite 100 recordings from that decade. One constraint was built into each mixtape to make it more interesting: I was allowed only one song per artist, which meant making genuinely difficult choices. One Beatles track for the 1960s, one ABBA or Bee Gees track for the 1970s, and so on. The playlist is a decade filtered through one set of ears, and the one-per-artist rule helped me keep the selection honest, not a tired “best of” collection for a select few artists.

If you’ve been on the fence about upgrading to a paid subscription, this series is an excellent opportunity to make that leap. Paid subscribers get all five playlists, full access to the back catalog of paid-tier content, and every paid-only post going forward.

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If you’re enjoying the content I’ve been posting (most) Mondays and Wednesdays, I invite you to share this post with someone who has opinions and, more importantly, a deep love of music. Word of mouth is how this community grows, and a forwarded email or a shared link is worth more than any algorithmic maneuvering.

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We’ll begin in June with the 1960s. Hope to see you there.

Genre: Rock, Art Pop, New Wave

Label: Warner Bros. Records

Release Date: May 19, 1986

Vibe: 💯

👉 Click the GIF to stream the album on your favorite platform

The story goes that Daniel Lanois nailed the studio door shut.

Not metaphorically. He physically bolted Peter Gabriel into the barn that had been converted into a two-room creative space on the grounds of Ashcombe House and went off for lunch. The former Genesis frontman and art-pop legend wasn’t allowed to leave the room until the lyrics for his eventual Kate Bush collaboration, “Don’t Give Up,” were finished. Gabriel eventually smashed through the door frame and was, understandably, pretty steamed. Lanois later said he “almost got fired,” but at least he got his message across. That wasn’t the first incident between the pair, either. Earlier in the recording sessions, Lanois had grabbed Gabriel’s phone mid-call, smashed it to pieces, and simply continued working. These are the measures that produced So, Gabriel’s finest achievement as a solo artist, his most controlled and precise outing in a discography filled with delightful, masterfully made oddities.

In several ways, his career serves as a useful microcosm for understanding a broader shift in rock music that began around 1973. At the time, he was the lead singer for one of prog’s most respected (and self-serious) groups. As their star rose, Gabriel’s stage persona grew more out of step with Genesis’s distinctive brand of complex arrangements, famously donning his wife’s red dress and a fox’s head mask on stage during the tour supporting Foxtrot. Eventually, strained relationships within the band led him to quit in 1975, kicking off a decade in which he prioritized studio experimentation, especially with sounds outside the British canon. He made four self-titled albums in seven years, each one more visionary than the last. His 1980 release, commonly referred to as Melt, introduced gated reverb drums before they became a cliché. Security, from 1982, is an infomercial for the Fairlight CMI synthesizer. These records were critically respected and commercially marginal until they weren’t.

In the mid-80s, the script flipped, and the sounds pulsing through many alternative and avant-garde scenes seeped into the mainstream. Gabriel scored his biggest pre-So hit with “Shock the Monkey,” which peaked at No. 58 on the Hot 100. Unlike someone like Bryan Ferry, who met mainstream early-80s tastes where they were compared to the stranger corners of Roxy Music’s discography, I’d argue that the marketplace met him on his level, or at least most of the way there. Right place, right time, as it were. The same goes for Gabriel’s So collaborators, chiefly Lanois, who was fresh off producing U2’s The Unforgettable Fire, and engineer Kevin Killen, who’d also helped craft several of the Irish outfit’s early hits. Despite the pedigree (the long list of celebrity cameos includes Stewart Copeland, Laurie Anderson, and Nile Rodgers), everything on So sounds slightly alien in texture. Gabriel had a penchant for recording multiple instruments on a single track and then bending them to his will, turning them into intriguing hybrid elements.

Recognizable but not quite categorizable … maybe that’s the best way to describe the underlying quality that makes this tracklist so pristine and engaging, rising above so many artifacts of that period sonically. “Red Rain,” written from a recurring dream about glass bottles filling with blood, makes that surrealism audible, with Copeland’s cymbals and hi-hat cascading over this impenetrable (but gorgeous) wall of processed sound. Gabriel had actually banned cymbals and hi-hats from his previous two albums, finding them too metallic, which makes their reappearance here important. It signals that the sonic vocabulary is expanding, not contracting. “Mercy Street” makes the same argument from a completely different angle. Written as a tribute to the poet Anne Sexton, it moves at a fundamentally slower pace, more submerged and experimental than anything you’d classify as “pop” on this LP. It’s all atmosphere and daring, refusing to explain Sexton or contextualize her work for those who don’t know it. It’s the track that asks the least of you and arguably lands the hardest.

Casual fans of 80s pop who may not be familiar with Gabriel’s oeuvre will almost certainly know or remember “Sledgehammer.” That level of recognition is due in large part to the music video, directed by Stephen R. Johnson and featuring stop-motion by Aardman and the Brothers Quay. It won 9 (!) MTV Video Music Awards in 1987 and remained the most-played video on MTV into the early 2010s. It’s a celebration of Black American music (Gabriel got Otis Redding collaborator Wayne Jackson to help him get the horns sound just right) with an art-rock edge to it, and it was also a throw-in at the very last minute. Gabriel’s session band had already wrapped and dispersed to other projects when he urged them to return to try something he had cooking on short notice. Drummer Manu Katché, who absolutely crushes it on the track, played his part in a single take. If you enjoy that rock-n-B energy, you’ll also dig “Big Time,” the artist’s takedown of yuppie consumer culture that, by that point, had already begun to poison Western culture’s well. Michael Douglas would proclaim “greed is good” a little over a year later and receive a (well-deserved) Oscar for his efforts.

Stacked up against all those highlights, the two most affecting cuts off So are case studies in emotional stoicism in the face of uncertainty. The first is the haunting duet “Don’t Give Up,” one that was originally offered (here’s a sliding doors moment for you) to Dolly Parton, who turned Gabriel down. The lyrics are written from the point of view of a man who has lost his job to Margaret Thatcher’s austerity measures, and who is staring down a path where he can envision his life unraveling quickly and painfully. Then, like a shard of light slicing between two clouds, Bush’s soft, soothing vocals emerge in the mix, giving him the courage to keep going. “Don’t give up ‘cause you have friends,” she tells him. “Don’t give up, you’re not beaten yet.” Around the duo, the arrangement is unassuming to a degree that it almost goes unnoticed. The synth chords and piano vamps hit your soul in the gentlest of ways, and the percussion somehow seems to move in time with your own heartbeat, regardless of when you press play. Landing somewhere between ASMR and a virtual therapy session, it’s utterly hypnotizing from beginning to end.

The same can be said for “In Your Eyes,” the song that Gabriel had always intended to be the closing track. It’s a deft blend of his infatuation with international, polyrhythmic shapes and cutting-edge studio technique, building on his fascination with African music in particular. 1982’s “The Rhythm of the Heat” is an early example of how he worked through this muse, though it’s not nearly as light on its feet or earnest as “In Your Eyes.” I’d go so far as to say the latter gets my vote for Gabriel’s best song. I’ve always adored Katché drumming, patterns I foolishly spent hours trying to emulate as an amateur player back in the day, as well as Youssou N’Dour’s vocal in the final section, rooted in Senegalese griot tradition and built around communal call-and-response. Both imbue the track with a spiritual quality that Gabriel has since described as intentional, calling it a “religious love song.” It doesn’t resolve so much as open outward, and at some point, you stop listening to it and start living inside it. Three years after release, Cameron Crowe captured its essence perfectly when he used it to augment the image of Lloyd Dobler holding a boombox outside Diane Court’s window in 1989’s Say Anything. That pairing of visual and sound is now permanent cultural shorthand for a specific kind of romantic vulnerability—making yourself completely visible to someone who may not want to (or know they need to) see you.

So is undoubtedly the record that defined Gabriel’s reputation, at once an achievement and an ongoing complication, since everything that came after it was measured against it, fairly or not. Us, which dropped six years later, sold a fraction of what So had despite being more personal on the songwriting front. The albums that followed into the 21st century have arrived to diminishing commercial returns. The question I’ve seen in several fan threads about this review is whether Gabriel traded something substantial to reach this commercial peak. By eschewing his previous experimentalism (though that’s not to say this LP has none to offer), it seems like he was more willing to lose listeners in service of a specific vision. The song-forward approach Lanois pushed him toward was more open, molding the ambition into a more digestible form that more people could enter. Gabriel was 36 when So came out, the four self-titled albums had built a real critical reputation but not a commercially sustainable one, and had it landed like its predecessors, the reasonable expectation was a long and respected career at the margins. Instead, he went mainstream, more or less kept his reputation, and spent the next 40 years standing in this album’s shadow.

What’s your favorite Peter Gabriel track? Add it to the comments.

Genre: Hip-Hop, Gospel, Alternative

Label: Self-Released (independent)

Release Date: May 13, 2016

Vibe: ⛪💗⛪💗⛪

👉 Click the GIF to stream the album on your favorite platform

When Chance the Rapper won a Grammy for Best Rap Album in 2017, he changed the music industry forever. Not because of his talent behind the mic (though he has that in spades, moreso when he’s not chasing Top 40 clout, but I suppose that’s also in the eye of the beholder), but instead because he became the paragon for a streaming landscape teeming with underground talent that was primed to explode. His mixtape Coloring Book was the first streaming-only project to take home a Grammy in any category, and that win led to sweeping changes at the Recording Academy a few months later. The importance of that last point shouldn’t be underestimated. The institution that crowns the best music of a given year had, to that point, treated streaming as a loophole rather than a legitimate format or platform. Chance forced them to rethink their definition of what counts.

A decade later, the conversation (I wanted to use the word “debate,” but again, I’m not positive it’s as black-and-white an undertaking as some think) around streaming as the default option for music consumption has only intensified. You only need to take a semi-close look at the economic side of the business (h/t ) or the notion that streaming, as a digital content ATM, is “minutes away” from becoming obsolete (h/t ) to understand how divisive the shift has become. But, if we’re being honest, even in 2016, that evolution felt inevitable. Netflix has already normalized the idea of renting your digital media for an affordable (in those days) monthly rate. Platforms like Tidal were gating and breaking albums from hip-hop and R&B’s most popular stars. A few global superstars even made a killing running in the opposite direction. I was working at a pop radio station at the time, and despite the station and program managers’ words to the contrary, the change was unstoppable. Streaming was the new cutting-edge, the place where what was cool lived.

In that sense, Chance the Rapper knew what he had and, naysayers be damned, held onto that advantage with all his might. By January 2016, he was three years removed from Acid Rap, the mixtape that had served as his initial coming-out party, and still no closer to signing with a major label. That’s not to say that big corporations hadn’t pitched him aggressively, because they had. But he’d turned every one of them down, including Ye’s GOOD Music, which, at the time, was the spot to be if you were a budding hip-hop star. Chance had ticked all other boxes: endorsements, XXL Freshman cover spot in 2014, and so on. All that left him oddly vulnerable, as he was seen as a critical darling with no distribution options, an artist operating solely on SoundCloud and Datpiff at a moment when the industry still couldn’t quite decide whether “free music” was synonymous with “commercially legitimate music.”

In September 2015, Chance’s trajectory changed again when his daughter, Kensli, was born. She had an atrial flutter, a heart condition that required immediate intervention, and the event had an immediate and lasting impact on him. He talked about quitting smoking and turning to his church for guidance. “All things are possible thru Christ who strengthens me,” he said on X. That discovery, and his experience contributing to the unabashedly spiritual exercise that is “Ultralight Beam,” off Ye’s Life of Pablo, clearly informed a lot of the aesthetic choices on Coloring Book. It’s more of a gospel record than straight hip-hop or R&B, with the rapper’s faith running through every track. What’s more interesting than that dynamic in a vacuum is how it allows him to create a dialogue with his former self. Under the posturing and layers of production, you can hear a young man, a new father, terrified by the reality staring him in the face. He has to reorganize his life and, creatively, build from a completely new emotional register.

Opener “All We Got” announces exactly what the record is going to be before the first verse ends. “Man, I swear my life is perfect, I could merch it,” he proclaims early on. “If I die, I’ll probably cry at my own service.” Every second of this track sounds celebratory—of life, or love, and of a global community that Chance makes clear later on gives him the conviction to practice his craft with such precision. “Music is all we got,” he adds. The Chicago Children’s Choir is another important throughline to highlight here, because they’re around for mere decoration. They appear on several songs, functioning as a structural glue on top of being a key textural element. It belies a specific set of roots, the center from which basically every other musical element on Coloring Book radiates outward. As he’d explain in several interviews during that and subsequent press junkets, Chance grew up in church, left, went back, and, after this daughter arrived, weaved it into his persona as a performer like few others have done in the 21st century.

On what ends up being a somewhat subdued tracklist, Chance still serves up several bops that bring ample energy to the party. “All Night” remains a seriously underrated weekend starter, with a suitably loopy Kaytranada groove somewhat obscuring the paranoid lyrics that Chance delivers with such cheerful remove that you don’t actually think it’s that big a deal. “No Problem” is even better, both in its club-ready trap structure and its fiery independent spirit. Flanked by Lil Wayne and 2 Chainz, two artists who also navigated the music industry as untameable voices, Chance rails against the labels that tried to meddle too much in his creative process. Otherwise, as he puts it, some of his posse will be waiting for the offenders in the lobby. As is the case more often than people might think, history was on the side of the artist. “No Problem” was the engine that propelled this project up the charts, reaching No. 43 on the Hot 100 and nabbed Chance another Grammy for Best Rap Performance.

The more I’ve returned to this record over the years (and I say this as a staunch atheist), this material is at its most compelling when it’s at its most soul-searchingly spiritual. “Blessings” is a good example: an out-and-out tribute to God that invites you in rather than preaching to you from up high. “I don’t make songs for free, I make ‘em for freedom,” Chance spits. “Don’t believe in kings, believe in the Kingdom.” That thread is extended with cuts like “How Great,” featuring genuinely uplifting harmonies and a welcome appearance from Jay Electronica, and “Finish Line / Drown,” which pairs T-Pain with Kirk Franklin and works better than maybe it has any right to. All those highlights aside, the best and most surprising track is “Same Drugs.” It’s so stripped-down, with no collaborators pulling Chance into competing aesthetics. Instead, it’s just him and a piano, writing about growing up and losing touch with people who used to know you. It’s the album’s quietest moment and the one that holds up most cleanly a decade later, with a melody that I’m glad was left to stand on its own.

The record arrived right before one of the richest summers ever for mainstream hip-hop and R&B. By shipping Coloring Book 11 days after Beyoncé’s Lemonade and two weeks before Drake’s Views, it put itself at the front of the line regarding the genre’s tastemakers in a crowded, mostly excellent field. Unfortunately, it looks like this record will be Chance’s defining moment as an artist. The Big Day, which dropped in 2019, landed badly, drawing the ire of online trolls and music critics alike for being earnest in all the wrong ways. For what it’s worth, I don’t think it’s as bad as all that, but it also doesn’t rise to the level that this project does. Few albums would be able to, if we’re honest. I didn’t love 2025’s Star Line, a release that most saw as a return to form but, even so, failed to recapture the momentum that made this one so special. It makes you appreciate circumstances when they converge like that, giving a burgeoning movement the spokesperson it didn’t know it needed.

What’s your favorite example of a small-scale, streaming-only record that hit it big? Before or since, doesn’t matter. Drop it in the comments.

Five new playlists are now live for your listening pleasure.

Each one explores a specific question, argument, or curiosity. They join the full Spotify library, which includes a paid back catalog of nearly 20 playlists. Access them here. If you’re not a Spotify user, TuneMyMusic transfers any of these playlists to the service of your choice in 2-3 minutes.

View All Playlists

Now, here’s what’s new:

Free Tier Playlists

Free Playlists

The best playlists are more thought experiments than mood boards (for me, anyway). I have little interest in creating something that’s essentially, “Here’s some soul music, see you later, bye.” Instead, I tend to pivot and think more along the lines of, “Here’s what the soul canon gets wrong about which records mattered.”

Less mythologizing, more exploring what those commonly-held cultural tenets leave out, purposely or not. These new free playlist additions are built along those lines.

The B-Side Was Better

38 tracks from artists who consistently saved something better for the people paying closer attention, whether that means deep album cuts or official B-side songs that served as counterpoints to the A-side radio hit hopefuls. Prince’s “The Beautiful Ones” over “When Doves Cry.” The Rolling Stones’ “Moonlight Mile” over “Brown Sugar.” D’Angelo’s “Spanish Joint” over “Untitled (How Does It Feel).” The argument holds across genres and decades.

Classic Rock That Actually Swings

39 tracks built around a single filter: does the rhythm section make you move before the guitar does anything? Featuring Bonham, Watts, the Meters, Humble Pie, ZZ Top, and a few dozen others who answered in the affirmative.

60s & 70s Soul You Should Know Better

Forty-two tracks from Hi Records, Philadelphia International, Stax, and Muscle Shoals featuring artists who were in the same rooms, with the same session musicians, at the same cultural moment as the songs you already know by heart, and still somehow didn’t make the short list. Doris Duke, Bettye LaVette, Timmy Thomas, Gloria Ann Taylor, and many more featured here.

If you’ve been thinking about upgrading to paid, the collection is at a point where it’s worth it. One price, hours of music to explore.

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For someone who has sold over 160 million records worldwide, making him one of the best-selling music acts of all time, and 85 million in the US alone, you’d be hard-pressed to find a stranger, more unexpected career arc than Billy Joel’s.

He spent the better part of a decade making records nobody bought before he ever became a household name. Between 1970 and 1976, he released four studio albums, moved to California under a management contract so punishing that it stripped him of every royalty and publishing right he owned, played piano in a bar under a fake name to pay rent, and watched each new release essentially disappear without a trace commercially.

For a while, he was genuinely invisible.

Then came The Stranger in 1977, and everything changed overnight. In the 16 years that followed, he saw four of his albums hit No. 1 on the Billboard 200, and enjoyed a run of pop-rock hits so consistent and so widely absorbed into American culture that they’ve become part of the furniture. I’d wager that many of you reading this don’t come to “Piano Man” or “We Didn’t Start the Fire” fresh, but rather with a brain that’s pre-loaded with a lifetime of associations to his music.

That dynamic is exactly why this studio album ranking exercise is worth doing. It forced me to look beyond familiarity and make decisions based on quality rather than reputation alone. While the hits are well-known, the more interesting debates lie in the less-trafficked corners of his discography, highlighting records that critics consistently dismissed, never warming to him in the first place.

Even if you think you know this oeuvre inside out, there’s likely a surprise or two in store for you.

Before we begin, the usual reminder to like, subscribe, and comment on what I missed or what changes you’d make to this list. You can also check out the other discography ranking deep dives I’ve published previously, including in-depth looks at the studio albums of the Beatles, Aretha Franklin, and many more.

12. Streetlife Serenade (1974)

Joel has said Streetlife Serenade is his least favorite of all his albums, and the production choices do not help its case in a revisionist sense. What saves it from being a pure write-off is Joel’s charisma as a performer. The portions of this record that work best are the ones where the arrangements give him plenty of room to speak plainly, and in several cases, air his petty grievances.

The best of those moments is “The Entertainer,” and maybe it’s because it had been a while since I’d heard it, but it plays as remarkably bitter. Joel torches the singer-audience contract with a knowing smirk, skewers the suits he had been forced to glad-hand, and takes a specific pot shot at Columbia for editing “Piano Man” down to a “suitable length” for radio without his blessing. “If you’re gonna have a hit, you gotta make it fit, so they cut it down to 3:05,” he sings at one point, which is deliciously ironic, because “The Entertainer” runs exactly … you guessed it, 3:05. Disc jockeys thought he was complaining about fame, even after Joel said repeatedly that it wasn’t the intent. “It’s a put-down,” he explained at the time. “Sticking a pin in the balloon of the performer.” The song hits hard either way, and the distinction mostly got lost.

Elsewhere, “Roberta” is looser and funnier, a portrait of a sad sack pining after a woman who’s clearly out of his reach, and “Los Angelenos” is an adequate stomper with more energy than most of what surrounds it on the tracklist. Outside those highlights, though, not much gets off the ground. Joel sounds tired, and more than tired, he sounds fed up with this version of himself. The horns feel borrowed and the strings reflexive. He was in the wrong city, working with the wrong people, under the worst possible contractual circumstances, and the record sounds like all three of those things at once. To add insult to injury, the album peaked at No. 35 on the Billboard 200 and eventually went Platinum, but Ripp’s royalty arrangement meant that every sale enriched a man Joel despised.

It isn’t a shock that he shed the vestiges of that LA existence and returned to New York for a reset. The move back east, and everything it unlocked, would more than make up for it.

11. Storm Front (1989)

I have a feeling this ranking may step on a few toes, but I found very little engaging or resonant about Storm Front. Instead, song after song, I couldn’t shake this overwhelming sense that I was listening to an artist who, despite having nothing left to prove, was still sprinting full-tilt on pop music’s hedonic treadmill, chasing the next commercial milestone at the expense of the distinctive soulfulness that Joel’s hugely successful late-70s and early-80s records contained in spades.

The stench of an overcorrection wafts through every crack and crevice of this tracklist. Following the more tepid commercial response to The Bridge (more on that album in a few minutes), he fired most of his band and parted ways with long-time producer Phil Ramone, the man who had figured out how to lend warmth to Joel’s storytelling without sacrificing any of the edge he sang or played with. Instead, the singer/songwriter brought in Foreigner’s Mick Jones, supposedly by way of a recommendation from Eddie Van Halen, who brought with him a big, tinny arena sheen that, for a lot of people, works well enough on the LP’s centerpieces but fits poorly on basically everything else. There are some charismatic flashes here and there, but Storm Front was, unfortunately, just a series of strange, borderline nonsensical choices.

Take “That’s Not Her Style” as an opening track. It’s a deeply weird and uncomfortably defensive ode to his ex-wife Christie Brinkley that’s aged about as well as you’d expect. Forget the cringeworthy mansplaining tone to it all, but my goodness, some of the writing is too icky to shrug off. At one point, after he says the papers imply she’s stepping out on him with another, potentially richer guy, he says: “And then she chartered a Lear when she heard her career was in danger/And gave the pilot somethin’ extra for a perfect ride.” Tell me you’re insecure about your marriage without actually saying those words, Billy. “I Go to Extremes” and “Shameless” are two other examples of songs that are far more toothless than their titles suggest, which is a specific kind of disappointment in its own right. It should be noted that Garth Brooks covered “Shameless” two years later and took it to No. 1 on the country charts. He’s even performed it with Joel multiple times. I wonder how well that sits with the latter party.

Then there’s “We Didn’t Start the Fire,” which, honestly, I can’t anymore with this song. I will pause for a moment and acknowledge that it hit No. 1 on the Hot 100 and, in the decades that followed, became such a cultural fixture that schools around the US have built parts of their history curricula around it, so, if hearing it means youngsters can rattle off the names of important world events a bit faster on an exam, there’s a sliver lining in there somewhere. But strip all that away, and you’re left with a gratingly mediocre song, one that Joel has since called his worst musical composition. The critique is easy enough to make: it’s repetitive and flat, and the lyrical conceit is even more annoying. Underneath the Forrest Gump-style inventorying of decades of geopolitical chaos, there’s a self-serving shoulder shrug that implicitly distances the Boomers from any accountability for any of it. Maybe they didn’t start the fire, but they certainly didn’t run in droves to get hoses and buckets to try to put it out. Forgive me, a millennial, for having exactly zero sympathy for the fallout from such inaction.

What saves the record from being a complete write-off is “Leningrad,” which at least tries to push past the corporatized sonic baseline and reach for something approximating genuine feeling. “And So It Goes” is similarly unguarded, but also so sonically spare that the piano ballad sounds like it wandered in from a different planet. Joel wrote it years before Storm Front came together, which explains the jarring stylistic shift right at the end of its runtime. I say all of this knowing I’m in the minority about this album, however. Storm Front topped the Billboard 200, went Platinum four times over, and (somehow) earned five Grammy nominations. It boosted Joel’s commercial prospects globally because it was engineered to do exactly that. Mission accomplished, I guess.

10. Cold Spring Harbor (1971)

Before Billy Joel was Mr. “Piano Man,” he was a cautionary tale about how the music industry can really screw you if you’re not careful. He recorded this debut under the thumb of Artie Ripp, owner of Family Productions, who had signed the 22-year-old Joel to a downright deplorable 10-record contract. The deal essentially stripped him of his rights to both the master tapes and the publishing on every song he’d ever write under its banner, which meant that, in the few years that followed, and as Joel’s star rose, particularly on FM radio, he didn’t see a dime of those royalties. Never forget to read the fine print, kids.

Back to the actual record. The sessions that produced this initial group of Billy Joel songs went smoothly enough, though you could safely call this a one-note soft-rock tracklist, too. Cold Spring Harbor is as much a product of the singer-songwriter boom that peaked in the early 1970s, with artists like James Taylor and Carole King finding success by stepping out from behind the beaded curtain of the for-hire lyricist and into the spotlight as performers in their own right. Joel was clearly trying his hand at crafting the kind of subdued, introspective record that was doing decent business in 1971, and there are glimmers of the talent that would later make him a global superstar.

Songs like “She’s Got a Way,” later a live show staple, and “Everybody Loves You Now” hint at the sophisticated storytelling of his upper-echelon material, particularly in the earnest, tender ballad lane. Also, I’ll say it now: Joel isn’t one to shy away from a cornball bit of songwriting if the opportunity presents itself. You have to meet the songs on that level if you hope to enjoy them to their fullest. I got some blowback in my “best of” Chicago article for putting “If You Leave Me Now” up there with the band’s best material. Everyone’s entitled to their opinion, of course, but the logic that everything they did tracked went downhill when they got “soft” won’t get you very far with Joel’s discography. You’ve been warned advised.

The legacy of Cold Spring Harbor was, for the longest time, the botched mastering. The tapes were transferred to vinyl at too fast a speed, raising the pitch of everything by a half-step and giving Joel’s voice a thin, chipmunk-like quality. Joel later said that he threw the finished record across the room when he first heard it back. I would’ve done the same. But Ripp, in his infinite wisdom, didn’t bother to correct the error, and, expectedly, the album sold virtually nothing. Columbia reissued a remixed, speed-corrected version in 1983, after Joel had become famous enough that the history mattered. The mastering disaster gets the headline because it’s the more dramatic story. But even a clean pressing would have been a modest debut. Cold Spring Harbor isn’t a great album. It was a sabotaged one, though, and there’s a difference.

9. River of Dreams (1993)

River of Dreams is, as of this writing, Billy Joel’s final studio album of pop originals, and despite releasing a surprise single in 2024, it seems likely to stay that way. Based on interviews he’s given this millennium, I don’t think he planned to make this LP his swan song, but the experience sounds agonizing enough that he didn’t want to put himself through it again.

“The thing was, I put a lot of work into River of Dreams, and it was as if the business had left me behind,” he told Vulture in 2018. “So I said, ‘What’s the point of putting myself through writing and recording if it doesn’t mean what it’s supposed to mean out there in the world?’” It’s amusing to read that portion of the interview and see the interviewer push back on Joel’s notion that it underperformed. After all, it did top the Billboard 200 on its initial release and sold millions of copies. But, when pressured for more insight, Joel replied bluntly: “I just had higher expectations for it. Then the record company [Columbia] came in and said, ‘Okay, what’s your next album going to be?’ And I went, ‘No, that’s it.’”

Of all the Joel records in this ranked list, River of Dreams was the one I was least familiar with, aside from the eponymous lead single, which has a fun 1960s throwback energy, not unlike what he did so well on An Innocent Man. Maybe it’s the fact that I went into this album listen with little-to-no expectations, but I dug it more than I thought I was going to. Granted, it’s Joel in full-on adult contemporary mode, so take that for what you will, but you can also hear the pedigree in every note. Joel’s flanked by a lot of top-tier studio talent on this record, including producer Danny Kortchmar, who’d worked with King, Taylor, Don Henley, Linda Ronstadt, and dozens of others. It sounds expensive and impressive, particularly on tracks like “All About Soul,” which feature a full gospel choir.

But, underneath all the polish, is a more measured, mature strain of Joel’s signature melancholy. There’s an understanding, especially on songs like “The Great Wall of China” and “Shades of Grey,” that life’s most meaningful conflicts seldom have clean resolutions. There’s also “Lullabye (Goodnight, My Angel),” a song written for his daughter Alexa, framed as a parent talking to a child about mortality and the persistence of love beyond death. It’s quietly one of the most devastating compositions in his entire catalog, a piano ballad so direct and free of self-consciousness that I was low-key stunned.

River of Dreams has often been talked about as Joel ending his studio output on a less-than-stellar note, but I’m not positive that’s actually the case. It was nominated for the Grammy Award for Album of the Year, and even if it didn’t blow people away, I think we’d all be talking about his legacy as a songwriter much differently had Storm Front been his final collection of original songs. It’s not like things didn’t work out for Joel, either. He has spent the past three decades performing to sold-out arenas and generally enjoying his time as a raconteur in interviews across various media formats. Not such a bad way to extend one’s career, if you ask me.

8. The Nylon Curtain (1982)

Long touted as Joel’s “statement album,” The Nylon Curtain has ambition to spare. Much of the songwriting sounds like a Boomer spokesperson working through frustrations and anxieties in real time as the US grappled with the early stages of the Reagan-era decline. On that level, it’s decently compelling, especially throughout its first side.

Opener “Allentown” sees Joel crafting a cutting portrait of post-industrial Pennsylvania (one that apparently served as a proxy for Bethlehem, where real-life mills and factories were shutting down weekly at the time). The found-footage nature of the song is well done, incorporating clangs and steam-whistle sound effects into the arrangement so seamlessly that you forget they’re there. There’s a nod to Bruce Springsteen and Don McLean in there, but it’s an arresting way to kickstart the LP. Elsewhere, “Pressure” is full of fire, featuring eight overdubbed synthesizers that push the sense of dread into the red. “Goodnight Saigon” runs seven minutes, opens and closes with the emulated sound of Bell UH-1 Huey rotor blades, built from a Roland synth and processed tom-toms, and was built from first-hand accounts about what Vietnam felt like from inside. It probably should have closed the album.

Instead, it lands mid-sequence, and the second side struggles under the weight of the concept it’s trying to carry. The tracklist post-"Saigon” isn’t awful, but the momentum and focused energy definitely take a hit. “Surprises” and “Scandinavian Skies,” the latter of which starts off promisingly, ultimately spin their wheels without adding anything of real substance to match what Joel pulls off in the first half. Joel has proven himself to be an exceptional architect of characters and mood, but incisive, politicized observation was never his sharpest tool, and the seams start to show after a while. “Where’s the Orchestra?” ends the record on a defeatist shrug, a man at a show that wasn’t what he expected, using theater as a metaphor for life. The idea is good. The execution, especially in tone, feels perfunctory.

If there’s an overarching issue with The Nylon Curtain, it’s the late-period Beatles influence that’s front and center. Joel’s acknowledged it openly, so it’s not like I’m speaking out of school here, but if you’re going to pay that kind of homage to that kind of band, it’s tough not to find yourself in a death-by-comparison situation if you don’t land the plane cleanly, and I don’t think Joel does that here. I appreciate the ambition and, overall, admire a lot of what he strives for song to song, but I can’t in good conscience put it up there with his best work. Joel has said he holds this album in higher esteem than The Stranger or 52nd Street, and there’s a growing segment of his fans that agree. But, in reality, it’s a strong half-album buried under thick dollops of pomp and circumstance.

7. The Bridge (1986)

In what became a theme for 1980s-era Billy Joel, The Bridge is mostly an exercise in hubris. It’s also more consistently entertaining than other records of his that have sold better and, somehow, garnered a much better reputation over the years. What that says about my taste, I’m not sure, but the confidence Joel writes and performs with here is off the charts and absolutely worth the price of admission.

Like a lot of mid-80s albums that I’ve written about, the production is where these songs show their age (see my Queen discography ranking for a few examples). It may have been a more cutting-edge, digital-first sound at the time, but there’s a flatness to the instrumentals that scrubs nearly all the emotional resonance out of the mix, prioritizing clean, smooth lines and surfaces instead. On one hand, it’s satisfying to hear the Swiss watch ticking away with as much precision as it does, but the trade-off is that the efficiency of the machine drains some of the life out of the material. If it were a bit looser and more carefree, you wouldn’t hear the gears turning as much.

What saves it from being a bore is Joel himself, both in front of and behind the mic. Even in the moments where he’s transparently riffing on other popular styles, the showmanship never wavers. “Running on Ice” sees him winking and nodding at Sting and the Police, transplanting a bass-forward minimalism to a New York setting. He pulls it off with enough conviction that the homage comes across as nothing short of loving. “Baby Grand” is a grand, showy duet with Ray Charles built on their shared reverence for the piano, and it works because Charles has an uncanny way of infusing such shameless gimmicks with boundless soul and elegance. “Big Man on Mulberry Street” turns Joel’s attention to a theatrical big-band arrangement that implies he had reached a point in his career where he could simply call whatever shot he wanted and no one would stop him.

And yet, those positives notwithstanding, the record was seen as a relative disappointment, commercially and creatively. Joel took the perceived failure hard, too, firing much of his band, severing ties with a lot of his production team, and taking his former manager to court. The Bridge didn’t cause any of that, but in retrospect, it reads like the beginning of a slippery slope to a career valley. It was also the last record to carry the Family Productions logo. Columbia’s president, Walter Yetnikoff, had finally pressured Artie Ripp into selling the publishing rights back to Joel. Fifteen years after signing that first catastrophic contract, Joel finally owned his own songs.

6. Piano Man (1973)

The secret here is as follows: Not only is Piano Man a hugely entertaining album, but the title track may be among its least impressive tracks.

Granted, it’s the song that most people continue to hear over bar or patio PA systems to this day, and if it’s your Billy Joel jam, I shan’t deprive you. But I do think it’s interesting that, even though it’s the track that initially made him famous, Joel has spent the better part of a half-century clowning on it publicly (see this conversation with Howard Stern as an example). To hear him describe it is to feel someone’s barely contained exasperation of how to play it over and over and over again for fans. Honestly, I get it. The song rambles, and the structure is more of a loop than a focused arc. What saves it is the specificity of the caricatures. The bartender named John, the real estate novelist, the piano man himself, each sketched only in a sentence or two, but they are all immediately recognizable as the kind of person you’ve met at least once. Joel was writing this portrait of losers with more compassion than condescension, and that instinct, more than anything else, makes the song stick.

The legacy of “Piano Man” tends to overshadow how great and how country the rest of the album is. It sits much closer to of-its-era Americana than what Joel’s artistic palette would evolve into. “Stop in Nevada” is this gem of a road song with a genuinely cinematic quality, tracing the geography of a woman leaving a relationship with wonderfully understated detail. “The Ballad of Billy the Kid” is even more ambitious, a sweeping narrative built on an orchestral arrangement that Joel would never attempt at this scale again. “You’re My Home” is a nice touch that conveys its sentiment without overreaching. These three tracks alone make the album worth more than its status as a footnote to the title track suggests.

The Columbia deal itself came about because of a song that would eventually end up on Piano Man, but, at the time, wasn’t yet recorded in a studio setting. A live radio performance of “Captain Jack” on Philadelphia’s WMMR in 1972 became the station’s most-requested song. This phenomenon caught the attention of the label’s promotions man, Herb Gordon, who brought it to then-president Clive Davis. Joel signed shortly thereafter, and the rest is history. The album peaked at No. 27 on the Billboard 200, and the title track reached No. 25 on the Hot 100. Modest numbers if you look at the scope of Joel’s career, but enough to keep him pushing toward the next industry milestone. The song was certified gold in 1975, though some Hollywood accounting left Joel with only $8,000 in actual royalties.

He was a proven hit-maker on paper and effectively broke in practice. That wouldn’t change for a while, either.

5. Turnstiles (1976)

This record is Joel’s true pivot point, and it sounds like one from the first note.

By 1976, he had moved back to New York and, for the first time in his career, recorded with the touring band he’d spent years building chemistry with on the road. Most notable among those players are drummer Liberty DeVitto, who’s been with him ever since, and bassist Doug Stegmeyer, who would also help anchor his sound for the next 15 years. The sonic upgrade from Streetlife Serenade to this LP is so noticeable, you kind of wonder why Joel hadn’t pulled the plug on the previous Los Angeles-based process that was clearly holding him back. Songs like the opener “Say Goodbye to Hollywood” ooze with this easy confidence, giving the arrangements momentum and gravitas in equal measure, all without ever coming across as strained. To the degree that Joel had swagger before, here’s where it finally kicked both doors down in one motion.

Not long after that moment comes probably my favorite Billy Joel song, “New York State of Mind.” It’s at the top of that list because, and maybe this will sound like an oversimplification, but it’s more than just a great song. Joel has plenty of those in his discography. What makes “State” special is that it serves as a wonderful declaration of identity. Through its layered, textural storytelling, you invited inside the mind of a man who’s, at long last, comfortable in his own skin as an iconoclast. He was done trying to fit into the idealized mold of a SoCal singer-songwriter and, relatedly, letting someone else’s ideas for him shape his music and career. To return to New York at a time when the city was broke and its luster had worn off significantly, and to find comfort in that homecoming, takes hutzpah. Joel flaunts his without apology.

What Turnstiles doesn’t get enough credit for is its range. Amid the full-throated rockers, you also get more nuanced tracks like “Summer, Highland Falls,” a quiet, aching ballad about someone who can’t find the middle ground between elation and misery. “Miami 2017 (Seen the Lights Go Out on Broadway)” is another highlight, a closer that finds an oddly satisfying lane as a sci-fi-cynicism piece that puts an exclamation point on his pro-New York stance. The piano playing across this record is worth singling out, too. It’s tighter and more varied than anything on his first three albums, folding in nods to jazz, classical, and R&B throughout. This album, more than any in Joel’s studio catalog, grows in stature the more you return to it, and the gap between what it sold initially and where it should stand now, legacy-wise, hasn’t been totally reconciled in the larger conversation about his career.

4. Glass Houses (1980)

When the research phase of this discography ranking turned its attention to Glass Houses, I kept reading that it was Joel’s hardest-rocking album. And, sure, that tracks … sort of. But that designation is also a great example of why genre categorization is kind of pointless. Is it rock? Is it pop? Is it closer to late-70s new wave? Maybe it’s even closer to an alternative scene that was bubbling over with fresh, exciting voices? Whatever you want to call it, the album is produced with a crisp, clean sensibility that keeps everything tightly wound without losing its sense of adventure or fun.

The most obvious comparison point for much of this tracklist is Elvis Costello, which is both a blessing and a complication. Joel pulls off that wiry, oddball rock vibe well on the deeper cuts, particularly “Sleeping with the Television On” and “Close to the Borderline,” both of which could’ve been hits for Costello, Joe Jackson, and several others who were thriving around the same time on college and FM radio. That energy also gives “It’s Still Rock and Roll to Me” its signature whimsical bounce. It’s kind of surprising that the track eventually became Joel’s first No. 1 on the Hot 100, only because it’s a bit mind-boggling that it didn’t happen sooner. It’s especially apropos since the song is a pointed defense of melodic, hook-centric songwriting that countered what Joel saw as the aestheticized aggression of punk. It feels genuine rather than calculated.

A couple of times, though, that alternative influence tips into thinner, more imitative territory. The closer, “Through the Long Night,” is the clearest example, a three-part harmony ballad that lands softer than much of the record around it and, for me, doesn’t put quite the exclamation mark on the album that you’d hope. What’s also worth honing in on, if purely for entertainment value, is the petulance running through all of Joel’s lyrics. He was pissed that critics kept treating him as a lightweight, and Glass Houses was his first serious attempt to shift that perception. He wasn’t wrong to try, but it’s funny to me that the record is still fundamentally a pop album, produced to a high sheen, full of melodic delights, and probably a bit too pleased with its own eccentricities to be taken seriously as a rebuke of his detractors. Unsurprisingly, critics didn’t warm to it.

Glass Houses reached No. 1 on the Billboard 200 and sold 7.1 million copies in the US, making it the 41st best-selling album of the entire decade (!). Joel also won a Grammy for Best Male Rock Vocal Performance, earning him the cultural currency he’d cash in for his next, more complicated studio effort. It marked the end of an era of sorts, as this was the last album to feature the original Billy Joel band lineup in full. Saxophonist and multi-instrumentalist Richie Cannata departed before the Nylon Curtain sessions.

3. An Innocent Man (1983)

Part fizzy love story, part rose-colored nostalgia project, An Innocent Man is a record that’s pushed my buttons in the best way possible since I first heard it over 25 years ago. And, in the age of everything-is-a-pastiche pop culture that we live in now, it’s arguably aged better than almost everything in his catalog. It occupies a space in my heart right next to the Grease soundtrack, as a loving, expertly executed homage to a decade I wasn’t around to experience in real time, yet it still carries a wonderful aural mystique whenever you spend time with this tracklist. It always puts a smile on my face.

As I listened to more music and broadened my stylistic palette, I was able to hear all the references Joel was making with these songs. The funky “Easy Money” is his play on a Memphis soul strut reminiscent of Sam & Dave or Otis Redding. “The Longest Time” is a gorgeous throwback to late-1950s doo-wop, and the effervescent “Uptown Girl” apes Frankie Valli & the Four Seasons. In lesser hands, it might’ve come across as a cheap imitation, but because the craft is never in question, you stay with him every step of the way. It doesn’t hurt that Joel’s vocals are also among the best he’s ever recorded, particularly on the ballads and doo-wop numbers. If you’re looking for a deep cut to hang your hat on, “Leave a Tender Moment Alone” is a genuinely impressive love song.

Speaking of which, let’s pause for a moment and mention the record’s main character, Joel’s ex-wife, Christie Brinkley. They had fallen madly in love and, according to the pop star, the experience made him feel “like a teenager” all over again. “When you’re gonna write [songs for a new album], you write what you’re feeling. And I didn’t fight it. The material was coming so easily and so quickly, and I was having so much fun doing it […] I think within 6 weeks, I had written most of the material on the album.” Listen, if I were in his shoes and started dating (and later married) Christie Brinkley, I’d be pretty jazzed about it, too.

The album reached No. 4 on the Billboard 200 and went Platinum seven times over in the US, producing two No. 1 singles in the process. More than the familiarity with the songs and styles of a cherished, bygone era, I’d like to think that a big reason for this record’s commercial success is how energetic and infectious the performances are. After the self-seriousness of The Nylon Curtain, going back to basics and making a record for himself first, without trying to carry the weight of some outsized political statement on his shoulders or sneer at his detractors in the critical community, was the right call. You can debate whether it was a necessary reset or the beginning of a different creative calculus, but the honest answer is probably both.

He’s having the time of his life and it still sounds like it, more than 40 years later.

2. The Stranger (1977)

Similar to the Boss in 1975, this make-it-or-break-it scenario brought out the best in Billy Joel.

It didn’t look so great to begin with, however. Columbia was ready to drop him and saw this LP’s production cycle as his final chance to recapture at least some of the magic from Piano Man. While shopping around for a producer who could make that happen, Joel approached Beatles scion George Martin, but the legend ultimately passed on the opportunity because he wanted session musicians rather than Joel’s band. Instead, the Long Island native turned to Phil Ramone, who was coming off the Paul Simon success, Still Crazy After All These Years, and whose feel for a certain type of New York sophistication aligned with that Joel had been building for himself. Even with that built-in chemistry, I don’t think either man expected the resulting songs to become as transcendent as they have.

More than anything, the trust between the key personnel is the x-factor between the notes here. The entire album was completed in just three weeks, with Ramone doing his part to emphasize the livewire in-person chemistry that Joel and his band had spent countless hours honing on the road. It’s what drives earworms like “Movin’ Out (Anthony’s Song),” “Only the Good Die Young,” and the criminally underrated “Get It Right The First Time,” the first two of which were Top 40 hits for Joel. Even its best-known song, “Just the Way You Are,” has this off-the-cuff lilt to it that draws you in from those first few iconic notes on the electric piano. That framing isn’t something you can fake with studio technology or multitrack smoke-and-mirrors. Sometimes, all you need is a motivated man and his piano.

The track that truly defines this album, at least for people like me who’ve spent considerable time with it, is “Scenes from an Italian Restaurant.” It’s essentially three different songs assembled into a single narrative arc, using the real-life backdrop of Fontana di Trevi, a restaurant near Carnegie Hall, as its setting. In seven minutes, you feel like you know these characters incredibly well. The lyrics move through romantic history, class aspiration, and the fond memories of one’s simpler, more youthful days and nights with such grace and ambition that I never tire of them. When it gets to the final minute or so, and it fades back to the present-day setting around the dinner table, it’s such a satisfying full-circle moment. If not Joel’s best song, then let’s call it his most cinematic achievement.

The Stranger was a runaway freight train right out of the gate. It spent six weeks at No. 2 on the Billboard 200 and was kept out of the top spot by another musical monolith, the Saturday Night Fever soundtrack. The LP has since sold more than 10 million copies in the US alone, earning it Diamond certification, along with hundreds of millions of streams across all platforms. It also turned what Joel considered a “gloopy” afterthought of a ballad in the recording process into an award-winning single when “Just The Way You Are” won Record of the Year and Song of the Year at the 1978 Grammys. He may scoff at it now, as he does with several of his other hits, but it’s now considered an out-and-out pop standard. Not too shabby for an artist who was dangerously close to being an also-ran.

1. 52nd Street (1978)

Controversy! Or is it?

How surprising a pick this is for the top spot in Billy Joel’s will depend on your relationship with his other work. He’s got multiple A-tier albums to his name, so it’s not like you’d be “incorrect” to go with The Stranger or even Glass Houses in place of 52nd Street. But, in my defense, it was the release that became his first chart-topping LP and won him the Grammy for Album of the Year, beating out the likes of Frank Zappa, Bruce Springsteen, and those pesky, disco-fied Bee Gees. Justified or not, The Stranger wasn’t even nominated.

What I appreciate that much more about this record is that he really swings for the fences and, in practically any case, he connects. After selling tens of millions of records, it would’ve been extremely easy for him to trot out The Stranger, Pt. II, and it would’ve been a massive success, but he takes no small number of chances sonically. It starts with the titular reference to the Midtown Manhattan hub for jazz hotspots, an influence that he incorporates throughout this tracklist. You hear it in the opening of “Stiletto,” my favorite deep cut of his, as well as “Zanzibar,” which builds around a Freddie Hubbard flugelhorn solo and marries it with reggae, jazz, and rock without ever losing its footing. On this most recent listen, I immediately put that track on repeat before moving on through the rest of the album. My goodness, it’s so good.

Elsewhere, “Big Shot” is the best kind of venomous rock anthem, obliterating New York socialite culture with so much swagger that it makes you pine for more of that in Joel’s catalog (sadly, I don’t think he ever went that hard with a rock arrangement ever again). There’s also “My Life,” which became a staple on soft-rock radio in no small part because of its tie-in with the Tom Hanks sitcom Bosom Buddies. Finally, for one more song pick, I adore “Until the Night,” a sweeping piano epic that ranks up there with Elton John’s most compelling material in the same style. There’s a version of 52nd Street that, in someone else’s hands, becomes overly smug and polished. I’m a huge Steely Dan fan, for example, but consider what Fagen and Becker might have done with the same raw material, in the same New York setting. You’d have a much colder, more sealed-off end product, without the working-class appeal that keeps it grounded.

Beyond the worldwide sales (over 7 million at the time of this writing) and numerous industry accolades, 52nd Street also represents another very important first in music history. It was the first commercially released compact disc, launched by Sony in Japan on October 1, 1982. 52nd Street bore the catalog number 35DP-1, the first in the sequence. I don’t have to tell readers of this newsletter that, if you come across one sitting in a used record store bin anywhere in the world, it’s worth scooping a copy.

Which Billy Joel album holds up best for you? Drop your vote in the survey below and make your case in the comments.

Genre: Rock, Funk Rock, Alternative

Label: Warner Bros. Records

Release Date: May 9, 2006

Vibe: 🌋🌋🌋🌋

👉 Click the GIF to stream the album on your favorite platform

It’s funny. I was only vaguely aware of the Red Hot Chili Peppers (RHCP) at the turn of the century, when they were at their peak creatively and commercially.

I knew of them, but I can’t say I was familiar enough to be any kind of fan of their music. Every kid in my high school could, at the drop of a hat, magically bang out the intro, first verse, and chorus of “Californication” on guitar, whether you wanted them to or not. Ditto for “Scar Tissue” and “Under the Bridge.” Anything that fell into the languid, more sorrowful category of their discography was insanely popular. And yet, I couldn’t have cared less. At that time in my life, I was too busy working backward through time, discovering and savoring every new morsel I could get from groups like Led Zeppelin, Black Sabbath, and the Jimi Hendrix Experience. Not a waste of time, per se, but I was definitely not plugged into the rock zeitgeist of the time. That is, until I heard Stadium Arcadium for the first time, and it blew my pants off.

More than any of their other records or eras—from the frenetic teeth-gnashing of Mother’s Milk to the funkier, slier Blood Sugar Sex Magik—this is their document of greatness. And it’s a document all right. 28 tracks, clocking in at a little over two hours, and, unlike some of the band’s LPs in the years since, surprisingly bereft of filler. The release is split into two distinct halves, Jupiter and Mars, and serves as a balanced showcase of their dual sensibilities. RHCP could mash and groove with the best of rock radio’s giants back then, but they were equally adept at creating what I’d call strange-but-beautiful alternative music. I’d argue they needed that extra layer, too, because rock music circa 2006 was in a specific kind of trouble. The critical establishment had largely handed the decade to the indies, favoring those who wrote three-minute songs that didn’t carry any arena aspirations. Nobody was waiting for a massive statement of a double album from a band in their 23rd year.

None of it felt inevitable within the band, either. By the time By the Way arrived four years earlier, RHCP were in a quiet crisis. Guitarist John Frusciante had seized the controls, steering the album toward Beatles and Beach Boys influences, replete with dense harmonies and orchestration. The rhythm section had been increasingly sidelined, and Flea, who had spent two decades developing one of rock’s most distinctive bass voices, found himself stuck in neutral. He later said he was dead set on quitting the band around 2004. But, thankfully for music fans, they reconciled and began the sessions for Stadium Arcadium in September of that year, at The Mansion in Laurel Canyon, the same house where they’d made Blood Sugar Sex Magik more than a decade prior. Kiedis described the writing room as more collaborative than ever. No one was forcing ideas down everyone else’s throats, and, sonically, the proof is audible.

The first disc opens with “Dani California” and immediately makes the case for the whole project. That opening drum crack from Chad Smith, the guitar line landing somewhere between surf rock and hard funk, and Kiedis tracing a character archetype he had invented somewhere around “Californication” through the history of American music. It’s not a happy ending, either: she dies at the end, shot in the back by a cop in Mississippi. It was also one of the last big hit songs of rock radio’s peak, peaking at No. 6 on the Hot 100 and holding the Alternative Airplay chart in the palm of its hand for a record-tying 14 weeks. It later won Grammys for Best Rock Song and Best Rock Performance. On that song and throughout Stadium, Chad Smith deserves a separate accounting. His contributions across such expansive material never become repetitive or meandering. He’s always been the secret MVP of the band for me, veering from hard rock to funk to soft-focus balladeering without ever letting the seams show.

He and Flea, whose bass is as much a load-bearing architectural element as Smith’s kit, are the structural reason this record doesn’t collapse under its own weight. The grooves are simply too good. “Tell Me Baby” is as Motown a moment as RHCP ever had, a staccato funk groove supported by Frusciante’s guitar switching between precision attack and wiry melodic runs at the drop of a hat. “Charlie” features incredible falsetto harmonies and two guitar solos running simultaneously, while “Warlocks” features Billy Preston on clavinet, one of his last recorded performances before his death, playing so far inside the pocket he sounds like a founding member. On “Jupiter,” every track knows what it was and absolutely breezes by.

The second disc, however, is a different animal entirely. “Desecration Smile” opens as a slow, circling acoustic piece that plunges into dissonance before finding resolution. “Especially in Michigan” pushed Frusciante’s guitar into stranger territory, alongside guest player Omar Rodriguez-Lopez of the Mars Volta. It sounds less like guitar give-and-take and more like diplomats negotiating a truce. And then there was “Wet Sand,” the song that justifies the double-album decision on its own. With its restrained guitar figure and Kiedis singing near a whisper, you keep waiting for it to take off, or at least stop withholding from you. Then the last minute-and-a-half arrives, with Frusciante erupting with the controlled abandon and the rhythm section, which had been holding the tension in place, finally opening the floodgates and letting it out. “Wet Sand” sees the Hendrix, Zeppelin, and Pink Floyd influences converge in grand, head-spinning fashion. I don’t think I’ve ever gotten over it.

Stadium Arcadium debuted at No. 1 on the Billboard 200, held the UK chart for 31 weeks, won four Grammys, and grossed over $80 million on the road. In 2025, Rolling Stone placed it among the 250 Greatest Albums of the 21st Century. The critical establishment had largely written off this strain of stadium-scale rock, and the band itself had nearly fractured before it was ever recorded. Neither the industry nor the band knew they needed this moment, but the reaction confirms that it was a much-needed return to form. They haven’t been able to pull off the same kind of comeback again, either. Frusciante left in 2009, came back in 2019, and the band released Unlimited Love in 2022. It sold well, but it was still only a good album by a band that had been great. Stadium Arcadium is what the difference sounds like.

What’s your go-to RHCP track? Show it some love in the comments.