10 Songs That Make the Case for Chicago as Pop-Rock GOATs

I walk you through the essentials from the legendary rock band's catalog.

Chicago’s problem has never been quality or mainstream appeal.

With well over 100 million records sold worldwide, 20 Billboard Top 10 hits, and 17 of their first 20 albums certified Platinum by the RIAA (good grief!), their commercial success is undeniable. Yet, when music conversations turn to the greatest rock bands of all time, Chicago gets mentioned far less than the usual suspects (e.g., the Beatles, the Beach Boys, and the Rolling Stones, etc.)

I think it’s a branding problem more than anything else. Hear the band’s name now, and most people jump straight to the soft-focus ballads that still get heavy playlist rotation. That’s not a knock. “You’re The Inspiration” is a genuinely good song. It just doesn’t tell the whole story.

Chicago didn’t survive shifts in pop and rock taste by accident. Their catalog spans far more than those two umbrella designations, from jazz fusion and political songwriting to disco-adjacent bangers and yacht rock balladry. Across six decades, they’ve done it all. This post is my attempt to get them the respect they deserve from casual fans who only know the hits.

It’s not a greatest-hits dump, either. Not entirely, anyway. Several of their biggest chart successes are absent from this list. Instead, I want to create a cross-section of what made them legends: their range, their control, their ambition, and their refusal to stagnate.

Enough blah blah. Hit that subscribe button if you want, but keep scrolling to begin your journey through Chicago.

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In alphabetical order, let’s begin:

1. “25 or 6 to 4” (1970)

From the opening seconds where that guitar and bass riff come in, you know this song’s a moment.

It was the demarcation point where Chicago stopped being a promising rock fusion experiment and started sounding, for lack of a better word, inevitable. The central groove is electric, folding in on itself, phrase after phrase, without losing its energy or its ability to transfix. Terry Kath’s lead guitar work is outstanding, bending tone and timing until the tension becomes so palpable you can feel it in your bones.

What keeps this song alive more than 50 years later isn’t its volume alone. It’s, perhaps counterintuitively, the restraint it shows. The rhythm section never rushes and the horns punch without cluttering the center of the mix. Even the famously opaque title, Robert Lamm’s shorthand for the time of night he was trying to write on a 12-string guitar, reinforces that idea of restless momentum. The single peaked at No. 4 on the Hot 100, making it the highest-charting single from Chicago II, and the band’s first genuine statement of intent.

The song may also have answered a question that hung over the band’s early career: Could Chicago make rock that hit as hard as some of their contemporaries? No one would mistake the band’s sound for something bluesier and harder-edged like Led Zeppelin or Black Sabbath, but there’s a part of me that thinks Kath and company had it in them, too. There’s a reason musicians who knew him personally still talk about him as one of the most gifted guitarists of his generation. Full stop.

2. “Beginnings” (1969)

“Beginnings” is a good example of how Chicago’s songs trust their audience. Many of their best cuts rely on patience and letting both melodies and hooks breathe, which aren’t qualities that necessarily lend themselves well to mainstream success. The song initially flopped on release and didn’t chart until Columbia reissued it in 1971, paired with “Colour My World.” The combined single climbed to No. 7 on the Hot 100, with “Beginnings” separately reaching No. 1 on the Easy Listening chart.

Not bad for a track people passed on the first time. Robert Lamm wrote this after watching Richie Havens perform at the Ash Grove in Los Angeles, and the influence is audible. The groove does most of the heavy lifting (shout out to those tasty Danny Seraphine drum fills), with a Latin-tinged rhythm that never feels borrowed or ornamental. When everything finally opens up in the second half, it feels communal rather than flashy.

The fact that it needed a second release to find its audience is also worth mentioning. The debut album it comes from, Chicago Transit Authority, was itself a slow build, proving impossible to ignore once consumers acclimated themselves to the band’s forward-thinking brilliance. The LP would eventually spend 171 weeks on the Billboard 200, setting a then-record for rock album chart longevity.

3. “Dialogue (Part I & II)” (1971)

How many rock bands can turn anxiety into a structural device for such a memorable two-parter?

The eponymous conversation bounces back and forth between two sparring partners in Part I. One man (whose portion is sung by Terry Kath) is disturbed by recent sociopolitical developments, such as the Vietnam War and the fallout from widespread famine. Meanwhile, the second man (sung by Peter Cetera) maintains an even keel, insisting that everything will be alright in the end. It’s all delivered without any sloganeering or overly neat conclusions. Instead, you’re asked to sit with ideas that are left unresolved.

Then Part II shifts the axis entirely. The horns rally, floating over the percussion elements like a bright sunrise over a cold winter landscape. The harmonies break through soon after, full of hope and optimism. Refrains like “we can make it better” and “we can save the children” cut through the uncertainty spoken in Part I, outlining a clear call to action for anyone who wants to actually make a difference, not just sing about it. By the time the song ends on collective momentum rather than resolution, it’s made its point more forcefully than any anthem could.

4. “Does Anybody Really Know What Time It Is?” (1969)

This song’s a good opportunity to hav e Robert Lamm sidebar. One of Chicago’s founding members, he wrote many of the band’s best-known hits, including several of the tracks included on this list. His piano playing has also provided the backbone for several others penned by his bandmates, such as “Colour My World.” As of this writing, he’s still touring with the group, too. Arguably the most jazz-influenced player on a lot of Chicago records, Lamm’s contributions are integral to their bright, bold sound.

Case in point is “Does Anybody Really Know What Time It Is?” Lamm’s opening piano solo is a marvelously relaxed flex, tempering its bounce with laser-like precision. It’s also quite difficult to pigeonhole into one specific genre or style. It’s reminiscent of classical and hard bop, but also 60s pop and R&B, undercutting all those influences with the notion that the world is moving too fast for anyone to really enjoy the spoils it affords many of us.

Lamm said of this track: “[It’s] not a complicated song, but it’s certainly a quirky song […] I wanted to write something that wasn’t ordinary, that wasn’t blues-based, that didn’t have ice cream changes, and would allow the horns to shine and give (founding member) Lee Loughnane a solo. So all that was the intent.” Decades later, there are few artists (save for maybe Billy Joel, who’s borrowed a few tricks from Chicago over the years) who could craft something as impressive technically.

5. “Hard to Say I’m Sorry / Get Away” (1982)

I have a story for you.

Years ago, my wife and I went to see Earth, Wind & Fire (my favorite band of all time) and Chicago on tour. At first, she was concerned she wouldn’t know enough of the latter’s songs to fully enjoy the experience, to which I replied, “Oh, don’t worry. You’ll know the songs from radio airplay when we were kids.” And, lo and behold, I glance over at her as the band wrapped an outstanding rendition of “Hard to Say I’m Sorry” and she had this shocked look on her face. “I didn’t know I knew all these songs,” she said. That’s cultural ubiquity at work, folks.

If you strip away its easy listening reputation, this song is a masterclass in temporal and emotional pacing. The first half (the half you likely know the best) leans into insecurity by way of hesitation. Peter Cetera’s delivery is measured almost to the point of stillness, as if he’s processing how he feels about the couple’s past romantic foibles in real time. It’s a rare case of early-80s male vulnerability on record without unnecessary adornment. As a result, the song more than earns the payoff of a slow piano fake-out before the transition.

Then the second movement hits. “Get Away” is this fun epilogue to what came before. Rhythm enters, momentum returns, and the whole thing justifies its construction. You can do with just the ballad portion, but the extended album cut with both parts makes for a more enriching listening experience. When it reached No. 1 on the Hot 100 in the summer of 1982 and stayed there for two weeks, it proved once again that Chicago really understood how to cater to mainstream radio without losing the relatability that ran through much of their material sung by Cetera.

6. “I’m a Man” (1969)

I like the original version of “I’m a Man,” recorded in 1967 by the Spencer Davis Group, more because I’m in awe of anything Steve Winwood wrote during that period of his life. But Chicago’s version vaults into this other sonic territory altogether. It’s looser and more communal, layered like a jazz-fusion jam session where everyone had a general understanding of the song and the chords they wanted to hit, but let the song take them where it wanted to go. There’s also a noticeable blues foundation in Lamm’s sawtooth keyboard playing and Kath’s swirling guitar interjections that keep it grounded in an edgier rock sensibility. It stretches and wails and sighs in ways so exhilarating they’ll take your breath away.

You also have Danny Seraphine’s drum performance, which is among his very best as a member of Chicago. With so many other incredible musicians that have graced the band’s roster over the years, Seraphine tends to get overlooked as one of the forces that shaped their music (he also left the group on less-than-stellar terms in 1990). It shouldn’t be that way, though. His ability to carry a groove on his shoulders and show off his free-flowing fill chops as he does in this song’s pummeling middle section deserves more recognition in the Chicago extended universe.

On another, deeper note, “I’m a Man” reveals important info about Chicago’s relationship with its influences. They were a band with a deep well of knowledge in rock, pop, jazz, and blues, but they never wore it as a “look at what we’re referencing” credential. The decision to cover a song written by Winwood and recorded with that singer’s signature vocal swagger, and then recast it with seven musicians playing off each other rather than funneling the energy through one individual, says a lot about what kind of band they were building in 1969. Collective musicianship over star power—it’s a theme that’s guided the band’s decision-making ever since, for better and for worse.

7. “If You Leave Me Now” (1976)

Peter Cetera’s tender, timeless ballad almost didn’t make Chicago X. He wrote it two years earlier, during the same sessions that yielded “Wishing You Were Here” on Chicago VII, and it was among the last tracks added to the former LP’s tracklist. Even the demo tape was cobbled together in an inauspicious way, with the band’s manager, James William Guercio, playing the acoustic guitar, assuming that Kath would finish it off the next time he was in the studio. Instead, his contribution is the one you hear on the final record.

Former Chicago saxophonist Walter Parazaider recalled hearing “If You Leave Me Now” on the radio and thinking it was McCartney-esque, and in general, he’s not totally off-base. Like a Sir Paul joint, nothing here is lazy. Every string swell is placed with care, augmenting the central French horn figure that oscillates between two notes and a refrain that’s compact enough to function as both the verse and the chorus. That level of restraint and concise construction takes a ton of confidence, not to mention craftsmanship, especially in a genre that, in the mid-1970s, tended to reward excess.

While some dismissed “If You Leave Me Now” as overly soft and sappy, the general public ate it up. The song became the band’s first-ever No. 1 single on the Hot 100, eventually selling 1.4 million copies in the U.S. alone and winning them the Grammy for Best Pop Vocal Performance by a Duo or Group. The easy-listening pivot it signaled was nonetheless fueled by the same discipline as their more complex, jazzier offerings. Cetera sang it with the kind of controlled fragility that’s genuinely hard to fake, and handed Chicago their commercial breakthrough in the process.

8. “Make Me Smile” (1970)

Here’s how you know Chicago was an incredibly ambitious rock outfit from the get-go: “Make Me Smile” began life as the opening movement of James Pankow’s “Ballet for a Girl in Buchannon,” a seven-part suite from Chicago II. It was eventually selected as part of that larger composition to be edited down into a standalone single, which was a good move for all involved. It became the band’s first-ever Top 10 hit on the Hot 100, peaking at No. 9, despite its endlessly restless nature. It dips and darts around sonic corners, continuously changing speeds and tone.

And yet, that fearless, fragmented nature is what makes it so compelling. It asks more of the listener than your average Chicago song, too, or certainly far more than the love song wing of their catalog. Kath sounds especially untethered here, pushing against structure with his lead vocals, invoking Little Richard and James Brown, all without letting the momentum flag. There’s a mesmerizing amount of trust between bandmates that’s readily apparent if you read between the lines. Everyone playing on the track was, at one point, asked to land transitions that shouldn’t work, but all do in this case. It’s controlled chaos at its most captivating.

The suite context matters, too. Chicago was one of a small handful of rock acts in 1970 willing to build a double album around an extended compositional structure rather than just a collection of ready-for-radio cuts. The Beatles had done it. The Who were doing it. Chicago doing it on their second album, before they had the kind of industry cred that would’ve made the experimentation more forgiving, was a genuine act of confidence. “Make Me Smile” works as a pop song, but it’s also an invitation: if you liked this, there are six more movements waiting.

9. “Saturday in the Park” (1972)

The most comforting of all the warm hugs that dot Chicago’s greatest hits, “Saturday in the Park” was a natural choice for the “Fun Song Friday” column I used to run as part of this newsletter. Robert Lamm wrote it after watching Fourth of July celebrations in Central Park in 1971, imbuing the lyrics with the wistfulness of witnessing a moving event as an innocent bystander. It peaked at No. 3 on the Hot 100 in 1972, one of three Top 5 singles Chicago had that year.

For more on the song’s significance, check out Brad Kyle ’s guest post about it from 2024. Here’s an excerpt:

“According to the song’s Wiki page, “the line ‘singing Italian songs’ is followed by ‘[Eh Cumpari](https://en.wikipedia.org/wiki/Eh,_Cumpari!)’ (the title of a song made famous by Julius La Rosa [in] 1953). Apparently, there’s been some debate about what follows next in the song, but in a video of Chicago performing ‘Saturday in the Park’ at the Arie Crown Theater in Chicago in 1972 (below), Lamm clearly sings, ‘Eh Cumpari, ci vo sunari,’ the first line of ‘Eh, Cumpari!’”: Just as that line can be heard in the hit Chicago recording!”

10. “Street Player” (1979)

Unfairly or not, critics despised Chicago 13 when it arrived in 1979. In their eyes, the band found themselves on disco’s mainstream assembly line, which struck reviewers and longtime fans alike as something more than opportunism. It was deemed a step down. Beneath their skill set and reputation. But what everyone missed was the intricacies from a harmonic and arrangement point of view that, frankly, and I say this as an out-and-out fan of the genre, plenty of disco practitioners couldn’t match, even if they tried.

The groove may be relentless, but it’s far from sloppy or hollow. A lot of disco and early house tracks would throw horns or other brass accents over top of a beat as window-dressing to brighten the whole affair up as much as they could. Because the brass section has always been so integral to Chicago’s sound, it flipped that instinct on its head. They drive the rhythm instead of being relegated to a supporting role. Years later, Kenny “Dope” Gonzalez lifted chunks of the track to build “The Bomb! (These Sounds Fall into My Mind)“ by The Bucketheads, which has lived on ever since as a house anthem. Without the source material, it’s far less exciting.

For those reasons, “Street Player” is one of the more satisfying redemption stories in Chicago’s catalog. The original critical and fan dismissal was so confidently dismissive that the taste gulf only looks more ridiculous in hindsight. You have to give it up to the band for essentially sticking to what made them great in the first place while updating their style to keep up with the times. They understood groove construction at a level most acts never approached, and producer Phil Ramone knew how to record rhythm with physical weight. They were building something that would matter long after the “disco sucks” backlash faded, even if they couldn’t have known it then.

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Which Chicago song still holds up best? Sound off in the comments.