It’s easy to overlook a band like Chicago when faced with their monumental accomplishments: an astounding 36 albums, 20 singles reaching the Billboard Hot 100 Top 10 (with three soaring to No. 1), and an impressive 17 of their initial 20 albums achieving Platinum certification from the RIAA. As one of the most commercially successful American bands in history, and as they celebrate the 50th anniversary of their groundbreaking debut album, Chicago Transit Authority, it’s crucial to delve into their music beyond the statistics. Let’s celebrate the collective of incredibly talented musicians who solidified Chicago’s place as a truly chameleonic force in rock’s golden era – effortlessly transitioning from experimental jazz-rock, funk, and soul to becoming an adult contemporary powerhouse.
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Chicago band members in 1970
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After navigating through Chicago’s extensive discography – remarkably, four of their first six LPs were double albums – Billboard has curated a list of the 50 best Chicago Band Songs. This selection spans their diverse range, from the deeply soulful and orchestrally rich early tracks crafted by guitarist Terry Kath, keyboardist Robert Lamm, and trombonist James Pankow, to the later, impeccably polished mega-hits produced by bassist/singer Peter Cetera and the renowned David Foster.
Find your personal favorites in our Spotify playlist below, immerse yourself in your headphones, and join us in honoring a band that continues to captivate audiences even in their sixth decade of rock and horns. Their 50th anniversary is not just a milestone, but a testament to their enduring legacy – and it feels like just the beginning.
50. “I’d Rather Be Rich” (Chicago XIV, 1980)
“Everything’s cool until you lose your money,” Robert Lamm wryly sings on this often-overlooked album track. It’s a sentiment that ironically reflects the commercial performance of Chicago XIV, which peaked at a modest No. 71 on the Billboard 200, a stark contrast to Chicago’s usual chart dominance. Despite its album’s reception, “I’d Rather Be Rich” is a catchy, upbeat song, filled with witty lyrics and vibrant percussion from Laudir de Oliveira, who departed the band after this album. – BOBBY OLIVIER
49. “Jenny” (Chicago VI, 1973)
Chicago VI, the first in a series of five consecutive albums recorded at James William Guerico’s Caribou Ranch in Colorado, reached the top of the Billboard 200, fueled by the success of singles like “Just You N’ Me” and “Feelin’ Stronger Every Day.” However, a more understated gem from this record is “Jenny,” a tender song penned and sung by Terry Kath about his dog of the same name. This soulful and poignant tune, where Kath asks Jenny to watch over his lover in his absence, gains deeper emotional resonance considering Kath’s tragic accidental death in 1978. – B.O.
48. “Hideaway” (Chicago VIII, 1975)
Chicago isn’t typically associated with heavy riffs akin to Tony Iommi, but the driving rhythm of the Chicago VIII deep cut “Hideaway” possesses a raw energy that might unexpectedly evoke early Black Sabbath. Even before the blistering guitar solo, there’s a palpable intensity. While Chicago found their greatest success with a softer approach, “Hideaway” is a powerful reminder of Terry Kath’s guitar prowess and the band’s ability to rock hard when they chose to. – ANDREW UNTERBERGER
47. “Little Miss Lovin’” (Hot Streets, 1978)
Hot Streets marked a significant sonic shift for Chicago. Following Terry Kath’s passing months prior, the band moved away from their signature jazz-rock style towards disco and pop influences. This stylistic change, which would define their sound throughout the 1980s, was initially met with skepticism by some fans. However, Hot Streets has aged surprisingly well, and “Little Miss Lovin’” stands out as a genuinely infectious pop-rock track. Listen closely, and you can even hear the Bee Gees contributing soaring background vocals. – B.O.
46. “Look Away” (Chicago 19, 1988)
If you dismiss Chicago’s post-Peter Cetera era, you’re missing out on some significant hits. Chicago 19 might be steeped in 80s sentimentality, but “Look Away” – the band’s only Hot 100 No. 1 single without Cetera and Billboard’s No. 1 song of 1989 for the year-end chart – is undeniably catchy. Penned by the prolific Diane Warren and featuring Bill Champlin’s powerful vocals, this track is a quintessential 80s earworm. “Look away, baby, look away,” indeed. – B.O.
45. “Stay The Night” (Chicago 17, 1984)
Beyond its memorable, action-packed music video, “Stay the Night” was a standout single from Chicago’s early 80s pop phase. From its opening drumbeat to the staccato synth verses and the melodic shift at the chorus, it’s captivating. While some of the lyrics (“I won’t take no if that’s your answer”) might sound dated today, the sneering, catchy chorus remains incredibly memorable, likely causing envy among bands like Foreigner who might wish they had come up with it first. – A.U.
44. “Along Comes a Woman” (Chicago 17, 1984)
Chicago’s polished pop craftsmanship reached its peak on Chicago 17, their best-selling album to date. All four singles from this record broke into the Hot 100 Top 20. The fourth and final of these was “Along Comes A Woman,” a Phil Collins-esque, high-energy track with a hook strong enough to overshadow the somewhat dated drum machine sound. – B.O.
43. “Gone Long Gone” (Hot Streets, 1978)
Here’s a moment to acknowledge Donnie Dacus, the accomplished rock guitarist who stepped into the immense void left by Terry Kath and played admirably on Hot Streets and Chicago XIII. Dacus, whose resume also includes collaborations with John Lennon, Billy Joel, and Elton John, delivers a particularly memorable Chicago guitar lick on “Gone Long Gone.” This breezy tune features Dacus’s piercing guitar melody as a counterpoint to Peter Cetera’s smooth vocals. – B.O.
42. “Song For You” (Chicago XIV, 1980)
Chicago XIV represented the band’s brief foray into a more introspective sound during the new wave era, a departure from their dance-pop approach. This experiment, however, proved short-lived. Cetera’s intimate “Song For You” is a prime example of this album’s direction. His more naturally produced vocal performance, particularly in his lower register, is almost unrecognizable yet remains tender as he reassures a lover of his dependability. – B.O.
41. “This Time” (Chicago XI, 1977)
Founding trumpeter Lee Loughnane is arguably Chicago’s most unsung hero. Beyond his signature horn contributions to countless Chicago hits, Loughnane penned excellent songs like “Call on Me,” “No Tell Lover,” and this lesser-known yet outstanding track from Chicago XI. On “This Time,” Loughnane delivers a commanding lead vocal, while Terry Kath’s guitar work is also a highlight. – B.O.
40. “Never Been In Love Before” (Chicago VIII, 1975)
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This charming romantic ballad from Chicago VIII was likely overlooked as a single due to its eclectic nature. The song shifts between sounds reminiscent of Supertramp and the Beach Boys, yet it retains Chicago’s quintessential heart and signature horn arrangements. Perhaps the title itself, “Never Been In Love Before,” on their eighth album, raised some questions: “What were all those other songs about, Peter?!” – A.U.
39. “Another Rainy Day in New York City” (Chicago X, 1976)
While Chicago X is best known for its second single, the chart-topping “If You Leave Me Now,” “Another Rainy Day in New York City” was technically the album’s lead single. This light, calypso-infused tune ironically contrasts its gloomy title. The intricate horn work is strong, and the song has aged well as a breezy, warm-weather track. – B.O.
38. “Waiting for You to Decide” (Chicago 16, 1982)
It’s no surprise that the renowned producer and songwriter David Foster played a key role in shaping Chicago’s shimmering 80s sound. He produced and co-wrote much of Chicago 16, and his melodic touch is evident in “Waiting For You to Decide.” This upbeat album track effectively sets the stage for the album’s later massive hits, “Hard to Say I’m Sorry” and “Love Me Tomorrow.” This is pure 80s, Cetera-era Chicago at its finest. – B.O.
37. “State of the Union” (Chicago V, 1972)
It might be hard to imagine now, but Chicago once saw themselves as social commentators, speaking out against war, politics, and the establishment. “State Of The Union” is a powerful, stirring track penned by Robert Lamm and sung by Peter Cetera, addressing themes of societal breakdown and the need for authentic political representation. It’s an exciting song with a message that unfortunately remains relevant today. – B.O.
36. “Will You Still Love Me” (Chicago 18, 1986)
“It wasn’t amicable, but it wasn’t the worst,” Peter Cetera told People Magazine in 1987 about his 1985 departure from Chicago. “It’s nothing that me having a hit and them having a hit won’t make better.” And so it happened: after Cetera’s solo hit “Glory of Love” reached No. 1, Chicago responded with their own lighter-waving ballad, “Will You Still Love Me.” The song’s brilliant piano intro and irresistible falsetto post-chorus propelled it to No. 3 on the Hot 100 in early 1987, essentially leveling the playing field between the Jason Scheff-led Chicago and their former frontman. – A.U.
35. “Aire” (Chicago VII, 1974)
Listeners who first put on Chicago VII might have been surprised to encounter a full 25 minutes of instrumental pieces before vocals finally appeared. This double album begins with five richly orchestrated instrumentals, the best of which is “Aire.” This sweeping composition opens with a grand horn solo before transitioning to Walter Parazaider’s flute and a masterful guitar section by Terry Kath. – B.O.
34. “Movin’ In” (Chicago II, 1970)
During their soulful early period, Chicago launched their blockbuster second album with “Movin’ In,” a sizzling piano-driven track featuring Terry Kath’s gritty, Joe Cocker-esque vocals. “Most of all we like to play/ A song or two that makes you feel/ Like all the good in you is real,” Kath belts out, with the band enthusiastically echoing “We know it!” after nearly every line, acting as both preacher and choir to their own musical gospel. – A.U.
33. “Take Me Back to Chicago” (Chicago XI, 1977)
“Take Me Back To Chicago” is a quintessential soft-rock track, brimming with nostalgia and Robert Lamm’s dynamic vocal performance. But on your next listen to this third single from Chicago XI, pay attention to the backing vocals – that’s Chaka Khan! It’s also hard not to appreciate the sharp keyboard solo by David “Hawk” Wolinski on this track. – B.O.
32. “What’s This World Comin’ To” (Chicago VI, 1973)
If Chicago were a hip-hop group, “What’s This World Comin’ To” would be their ultimate pass-the-mic anthem. Robert Lamm, Peter Cetera, and Terry Kath trade lead vocals, questioning the state of a world plagued by hunger and poverty. But the most striking moment of this funky and vibrant song is its opening, where Kath boldly declares, “We can cut it in any key.” Chicago needed more of these unapologetically bold moments. – B.O.
31. “Happy Man” (Chicago VII, 1974)
This closing track on the jazzier first LP of Chicago’s 1974 double album is an unassuming, sun-drenched tune. It glides along with a light samba rhythm and features one of Peter Cetera’s most blissful early vocals. Cetera even adds a bit of “skittle-ee-bee-bop!” scatting at the end, but his portrayal of the song’s “Happy Man” character is so convincing that it’s hard to fault him for getting carried away in the moment. – A.U.
30. “Wishing You Were Here” (Chicago VII, 1974)
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Opening with the gentle sound of ocean waves, “Wishing You Were Here” is a sublime example of mid-70s soft rock melancholy at its most evocative. Adding to its beauty, Chicago’s tourmates, The Beach Boys, contribute backing vocals on the song’s recurring refrain, transforming each expression of longing into a powerful wave of five-part harmony. – A.U.
29. “Hard Habit to Break” (Chicago 17, 1984)
Chicago 17 stands as one of the quintessential power ballad albums, especially of the 1980s, and “Hard Habit to Break” is a prime example. With a monumental melody crafted by songwriters Steve Kipner and Jon Parker and powerful vocals from Peter Cetera and Bill Champlin, this is the kind of Chicago track perfect for “rolling down the windows and singing along as loud and off-key as possible.” It’s a testament to the band’s successful evolution in their second act. – B.O.
28. “In the Country” (Chicago II, 1970)
The magic was palpable on Chicago II. The sheer creativity and boldness in blending rock and jazz throughout this expansive double album were remarkable. There was also a deep vein of soul, largely driven by Terry Kath’s passionate vocals and searing guitar work. “In the Country,” a sweeping love letter, perfectly embodies this. Kath’s beautiful lead vocal is enhanced by Cetera’s backing harmonies. It’s a fitting conclusion to the album’s first side, setting the stage for the acclaimed “Ballet For a Girl in Buchannon” suite. – B.O.
27. “Street Player” (Chicago XIII, 1979)
The standout track from Chicago’s brief disco era, “Street Player,” was written by Chicago’s Danny Seraphine and David “Hawk” Wolinski but was initially recorded by Rufus & Chaka Khan for their 1978 album of the same name. Surprisingly, Chicago’s rendition, released a year later, is the funkier version, tighter, punchier, and featuring an absolutely killer horn hook. This hook improbably permeated two later generations of jock jams, sampled in pop hits by The Bucketheads and Pitbull. – A.U.
26. “Alive Again” (Hot Streets, 1978)
“Alive Again” served as a kind of re-introduction for Chicago. While they hadn’t been away long – Chicago XI had just been released in the fall of 1977 – this was their first single after Terry Kath’s tragic death and the band’s decision to continue without him. “Alive Again,” a bright and worthy track written by trombonist James Pankow, showcased their more pop-oriented direction. It sounds like it could be a Fleetwood Mac Rumours B-side. – B.O.
25. “Feelin’ Stronger Every Day” (Chicago VI, 1973)
One of the most upbeat breakup songs ever written, Peter Cetera co-wrote this 70s radio staple with James Pankow about “healing and moving on after a relationship ends.” With its bright horns and repeated “Oh-ohhhh yeah!” exclamations, Cetera sounds genuinely energized about moving forward. To underscore this feeling of renewed strength, the song shifts into double-time towards the end, maintaining momentum right through the fade-out. On to the next chapter, indeed. – A.U.
24. “Lowdown” (Chicago III, 1971)
The story goes that “Lowdown” caused some tension within the band. Terry Kath was reportedly unhappy about Peter Cetera, primarily known as a bassist and singer, contributing more to songwriting. He was also reportedly not fond of the guitar part written for “Lowdown.” Nevertheless, this catchy tune became the album’s second single and a fan favorite from Chicago III. Cetera: 1, Kath: 0. – B.O.
23. “It Better End Soon” (Chicago II, 1970)
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“With this album, we dedicate ourselves, our futures and our energies to the people of the revolution. And the revolution in all of its forms.” This rebellious message was inscribed on the inner sleeve of the Grammy-nominated Chicago II album, alongside the lyrics for “It Better End Soon.” This 10-minute Vietnam War protest epic, divided into four “movements,” is a powerful fusion of Hendrix-inspired rock and jazz, with Terry Kath’s valiant vocals and Robert Lamm’s songwriting. It’s a dynamic and expansive piece of music. – B.O.
22. “Dialogue, Pts. I and II” (Chicago V, 1972)
“Dialogue” is a musical conversation between Terry Kath and Peter Cetera, touching on various early 70s topics. It likely mirrored the creative push-and-pull between these two key figures in the band, perhaps more than fans realized at the time. Released during a period of immense commercial success for Chicago, it still reached the Top 40 despite lacking a traditional chorus or obvious hook. In its full seven-minute, two-part version, it showcases the band’s skill in blending progressive ambition with pop accessibility, almost convincing you of their “We can change the world now… we can make it happen!” aspirations. – A.U.
21. “Beyond All Our Sorrows” (Chicago VI reissue, 1973/2002)
“Beyond All Our Sorrows” is arguably the rawest track on this list. It’s a gritty solo demo by Terry Kath, unreleased on the original Chicago VI but included in the 2002 reissue. Kath’s vocal is pure soul and unbridled emotion as he wails over a lone piano (possibly played by himself), reflecting on the painful question: “Why do I always hurt the ones I love?” If you haven’t discovered this previously unreleased song, filled with both power and vulnerability, it’s highly recommended. – B.O.
20. “Free” (Chicago III, 1971)
At a concise 2:16, “Free” is the shortest track on this list, yet it packs a significant punch. Terry Kath leads the powerful “I just wanna be free!” chant over roaring horns and guitar. This quick, energetic track, the third of six parts in Robert Lamm’s “Travel Suite” on Chicago III, was the album’s lead single in 1971 and remains a beloved fan favorite nearly 50 years later. It’s a straightforward and instantly enjoyable song. – B.O.
19. “No Tell Lover” (Hot Streets, 1978)
While the lyrical theme – an ode to extramarital affairs – may not have aged perfectly, “No Tell Lover” remains a beautifully crafted song from Chicago’s transition into soft-rock prominence. Peter Cetera delivers a tender vocal, supported by Donnie Dacus’s gentle harmonies and guitar work. “No Tell Lover” reached No. 14 on the Hot 100 and was Chicago’s last Top 50 hit for four years until “Hard To Say I’m Sorry” emerged. – B.O.
18. “Baby, What a Big Surprise” (Chicago XI, 1977)
As we move into the section of monster ballads, “Baby, What a Big Surprise” is a standout soft-rock smash. It reached No. 4 on the Hot 100 and became Chicago’s final Top 10 hit before Terry Kath’s passing (and also the band’s split with long-time producer James William Guercio). As Peter Cetera sings his version of “you like me, you really like me!” to an unnamed lover, Beach Boys icon Carl Wilson contributes rich background vocals. Lee Loughnane’s captivating piccolo trumpet performance is also legendary on this track. – B.O.
17. “Old Days” (Chicago VIII, 1975)
Opening with a riff reminiscent of Pink Floyd’s “In the Flesh,” the biggest Hot 100 hit from Chicago VIII quickly transitions into sweet nostalgia. It features bright horns, sweeping strings, and lyrics yearning for “a world gone away.” This is a style that Cetera and Chicago have long excelled at. However, the distorted guitar and groaning organ underpinning “Old Days” give it enough edge to prevent it from becoming overly sentimental. – A.U.
16. “(I’ve Been) Searchin’ so Long” (Chicago VII, 1974)
“(I’ve Been) Searchin’ so Long” isn’t just the best song on Chicago VII; it’s adult contemporary perfection. Peter Cetera’s smooth vocal is as comforting as a vanilla milkshake, beautifully contrasted with the somber symphonic intro (arranged by James Pankow). The yearning in the lyrics feels genuine, the harmonies are exquisite, and as Cetera explores self-discovery, the song builds to a compelling, R&B-infused climax in its final minute. It’s a true musical journey. – B.O.
15. “Make Me Smile” (Chicago II, 1970)
For all of James Pankow’s songwriting contributions over five decades, “Ballet For a Girl in Buchannon” – the epic seven-part suite from Chicago II – is certainly among his most significant works. It’s a masterpiece that begins with the upbeat “Make Me Smile,” a powerful section that was edited into a radio single and became Chicago’s first-ever Hot 100 Top 10 hit. Terry Kath delivers a characteristically passionate vocal performance, setting the stage for Chicago’s immense success throughout the 70s. – B.O.
14. “Poem 58” (Chicago Transit Authority, 1969)
From a period when Chicago could be seen as peers to both Santana and The Carpenters, “Poem 58” is – somewhat ironically, given its title – primarily instrumental for most of its eight-and-a-half-minute duration. Terry Kath delivers an absolutely blistering guitar performance throughout this acid-tinged groove. When Robert Lamm’s lyrics finally enter after five minutes, the song transitions from a frenetic jam to a still-intense amble, but the focus remains on the guitars, snarling through a jam potent enough to convert “If You Leave Me Now” skeptics into devoted fans. – A.U.
13. “You’re the Inspiration” (Chicago 17, 1984)
Whether you experienced this sentimental ballad’s mid-80s ubiquity firsthand or first encountered it as a kitschy cameo in the 2016 movie Deadpool, the sheer magnitude of its chorus is undeniable. Originally written for Kenny Rogers, as Cetera mentioned in a 2004 interview, “You’re the Inspiration” climbed to No. 3 on the Hot 100 in early 1985 (surpassed only by “Like a Virgin” and Jack Wagner’s even cheesier “All I Need”). It was a major factor in making Chicago 17 the band’s best-selling album to date. – B.O.
12. “Something in This City Changes People” (Chicago VI, 1973)
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“Something in This City Changes People” might be the best non-single in Chicago’s entire catalog. It carries a grayscale, melancholic vibe as Robert Lamm, Terry Kath, and Lee Loughnane deliver magnificent vocals about the harsh realities of urban life. The descending “so sad, so sad” harmonies cut deeply over Lamm’s warm, unforgettable piano melody. Laudir de Oliveira’s subtle conga rhythms complete the arrangement, creating a deeply underrated gem from Chicago’s early years. – B.O.
11. “Love Me Tomorrow” (Chicago 16, 1982)
The question was: how could Chicago possibly follow up the No. 1 success of “Hard To Say I’m Sorry,” which was virtually inescapable in 1982? The answer: with another impeccable soft-rock hit, this time with a bit more edge. “Love Me Tomorrow,” another Cetera/Foster collaboration, with its chest-thumping chorus, is pure pop perfection, lean and powerful. – B.O.
10. “Colour My World” (Chicago II, 1970)
Returning to “Ballet For a Girl in Buchannon,” we highlight the suite’s fifth movement, “Colour My World.” This beautiful passage is sung by Terry Kath and written by James Pankow, using color as a metaphor for love’s presence in life. Robert Lamm’s gentle piano part is memorable, as is Walter Parazaider’s soaring flute solo. The story goes that Pankow conceived the arpeggiated melody while on tour, staying at a Holiday Inn – proving that inspiration for rock history can strike anywhere. – B.O.
9. “If You Leave Me Now” (Chicago X, 1976)
“If You Leave Me Now” represents Chicago’s definitive step into easy-listening territory, and perhaps not coincidentally, it became their first of three Hot 100 No. 1 hits. Despite distancing the band from their Transit Authority origins, “If You Leave Me Now” remains a stunning piece of music, particularly for its efficiency. The entire song revolves around a French horn riff that oscillates between just two notes and a poignant two-line refrain that functions as both verse and chorus. The song’s pleas are simple and heartfelt, requiring no further elaboration. And when Cetera runs out of “ooh-oohs,” he steps back and lets the acoustic guitars convey the emotion. – A.U.
8. “I’m a Man” (Chicago Transit Authority, 1969)
“I’m A Man” pulsates with more raw energy than most Chicago songs. This stone-cold Chicago classic (co-written by Steve Winwood and originally released by his Spencer Davis Group in 1967) has a frenetic drive, fueled by Terry Kath’s searing guitar work and a captivating vocal interplay between Kath, Peter Cetera, and Robert Lamm. While technically a cover, “I’m A Man” became integral to Chicago’s early repertoire. Danny Seraphine’s extended percussion solo added a fresh dimension to the song when released on Chicago’s seminal debut. – B.O.
7. “Just You N’ Me” (Chicago VI, 1973)
“Just You and N’ Me” is Chicago’s greatest love song, unequivocally. This simple yet deeply passionate composition was penned by James Pankow, who recounted writing it after an argument with his fiancée. “We had a disagreement, and rather than put my fist through the wall or get crazy or get nuclear, I went out to the piano, and this song just kind of poured out,” Pankow shared on Chicago’s website. “Just You N’ Me” reached No. 4 on the Hot 100, becoming the highest-charting single from the beloved Chicago VI album (and its sheet music was even used for Pankow’s wedding announcement). – B.O.
6. “Questions 67 and 68” (Chicago Transit Authority, 1969)
This is where it all began. “Questions 67 and 68” was Chicago’s debut single, a triumphant inquiry written by Robert Lamm reflecting on an uncertain romantic relationship he experienced in – you guessed it – 1967 and 1968. The piano chords ring out confidently, and the horns blare harmoniously, never relenting from the song’s opening. But perhaps the most memorable elements of “Questions” are Cetera’s effortlessly cool “ooh’s.” “Questions” was, of course, a precursor to all that Chicago would achieve, but even beyond its historical significance, it remains a stellar jazz-rock jam. – B.O.
5. “Beginnings” (Chicago Transit Authority, 1969)
Like an evolved “Crystal Blue Persuasion,” Chicago’s second A-side (re-released more successfully two years later after initially missing the Hot 100 in 1969) shares the same bubbling bassline and relaxed, Sunday morning guitar feel as that Tommy James and the Shondells classic. However, “Beginnings” is elevated by Robert Lamm’s triumphant soul vocal – arguably his finest – along with its brilliant use of non-verbal exclamations to convey overwhelming emotions. The song’s expansive eight-minute runtime allows it to truly develop, culminating in “Only the beginning!” chants that propel the band into a near-spiritual fervor. Is it any wonder that beginnings like this led to such a consistently successful career? – A.U.
4. “Does Anybody Really Know What Time it is?” (Chicago Transit Authority, 1969)
It might be surprising to learn that when Chicago entered the studio to record “Does Anybody Really Know What Time It Is?” – their first song recorded together and a future classic rock staple – they were quite unsure of their approach. “We tried to record it as a band, live, all of us in the studio at once,” Walter Parazaider recalls on the band’s website. “I just remember standing in the middle of that room. I didn’t want to look at anybody else for fear I’d throw them off and myself, too. That’s how crazy it got.” They eventually figured it out, of course, perfectly capturing Robert Lamm’s genre-bending anthem of late-60s disillusionment: “We’ve all got time enough to die,” he croons, certainly giving the person who asked him for the time far more than they bargained for. – B.O.
3. “Saturday in the Park” (Chicago V, 1972)
Ah, the quintessential feel-good Chicago song and one of their signature tunes, “Saturday in the Park” emerged from Robert Lamm’s interpretation of film footage he had shot in Central Park years prior. As he recalled to Billboard in 2017: “I watched the film [and] I jotted down some ideas based on what I was seeing and had experienced. And it was really kind of that peace and love thing that happened in Central Park and in many parks all over the world, perhaps on a Saturday, where people just relax and enjoy each other’s presence.” The scene Lamm paints (and sings with such joy) in “Saturday” creates a miniature utopia of laughter, dancing, and ice cream vendors. Fans embraced this dreamscape, propelling this “real celebration” to No. 3 on the Hot 100 – Chicago’s highest-charting single at that point and their first to sell a million copies. – B.O.
2. “Hard to Say I’m Sorry” (Chicago 16, 1982)
As disco faded and MTV redefined rock and pop in the early 80s, there were doubts about Chicago’s ability to survive and thrive in the new decade. However, with the help of writer-producer David Foster, the band soared back to the top of the Hot 100 with their most undeniable ballad to date. “Hard to Say I’m Sorry,” a piano-driven plea for forgiveness, with its airy production, couldn’t mask the song’s underlying songwriting strength. From its captivating opening line (“‘Everybody needs a little time away,’ I heard her say…”) to its masterfully executed climactic key change, it’s a masterpiece. Of course, Peter Cetera’s vocal brilliance is essential, giving his full power to every “I WILL MAKE IT UP TO YOU!” promise. But the song’s enduring quality is evident in the numerous covers it has received over the years. – A.U.
1. “25 or 6 to 4” (Chicago II, 1970)
There’s a reason why Chicago has chosen “25 or 6 to 4” as their set closer for almost every concert this century, including their Rock and Roll Hall of Fame induction in 2017: It’s their greatest song, perfectly encapsulating the rock, soul, and horns sound that has brought this sprawling band immense success over the past 50 years. “25 or 6 to 4,” written by Robert Lamm during a sleepless night in Los Angeles – he insists the lyrics are not about drug use, despite decades of speculation – became Chicago’s first Hot 100 Top 5 single (No. 4) and helped introduce their jazz-infused style to mainstream audiences. The song has endured not only on classic rock radio but also on high school football fields, as marching bands across the country continue to favor this towering tune. Beyond the blaring brass, there’s an unforgettable performance from Terry Kath, who unleashed crunching hard rock guitar, and Peter Cetera’s urgent, soaring vocals. “25 or 6 to 4” is a full-band triumph from one of the greatest big-band rock acts of any era and the ultimate Chicago band song. – B.O.
