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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.
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.
Completely ignored rock, including ballads.
Aerosmith's I wouldn't wanna miss a thing was a dominant song and better than a lot on this list.