If you ask a casual listener to name a few tracks for a songs by chicago list, they’re almost certainly going to start huming "You're the Inspiration" or "Hard to Say I'm Sorry." It’s inevitable. Peter Cetera’s soaring 1980s ballads are burned into the collective consciousness of anyone who ever stepped foot in a dentist's office or attended a junior high prom. But here’s the thing: that version of Chicago—the power-ballad machine—is actually the "sequel" to one of the most experimental, aggressive, and musically complex rock bands America ever produced.
The real tragedy of the band’s legacy is how the slick, David Foster-produced era completely eclipsed the period when they were essentially a jazz-fusion group with a political chip on their shoulder.
They were originally the Chicago Transit Authority. The city actually sued them to change the name, which is honestly a pretty rock-and-roll way to start a career. From 1969 to about 1977, they weren't just making hits; they were stretching the limits of what a "pop" band could actually do on the radio. If you really want to understand their impact, you've got to look past the wedding songs.
The Terry Kath Factor: The Soul Chicago Lost
Most people don't know that Jimi Hendrix once told saxophonist Walter Parazaider, "Your guitar player is better than me." He was talking about Terry Kath.
Kath was the heart of the original lineup. He had this gravelly, soulful voice that sounded like it had been soaked in whiskey and cigarette smoke, and his guitar playing was nothing short of volcanic. When you look at an early songs by chicago list, tracks like "25 or 6 to 4" stand out because of that iconic riff, but it's Kath's solo at the end that really defines the era. It’s a blistering, wah-wah-soaked masterclass in controlled chaos.
Then there’s "Introduction," the very first track on their debut album. It’s a seven-minute manifesto. It shifts from jazz-inflected brass lines to heavy blues-rock and back again without breaking a sweat. It basically tells the listener, "We aren't a three-minute-single band." Sadly, Kath died in a tragic accidental shooting in 1978. It wasn't just a loss of a member; it was a loss of the band's grit. Without Kath, the band drifted toward a softer, more keyboard-driven sound that eventually led to the 80s dominance we all know.
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Honestly, if Kath had lived, the 80s might have looked very different for them. They probably wouldn't have become the kings of adult contemporary. They might have stayed weird.
Decoding the Suites: Why 1970 Was Their Peak
In 1970, Chicago released Chicago II. It’s a double album. Think about that for a second. Their first three releases were all double or triple albums. That is an insane amount of confidence.
The centerpiece of their second album is "Ballet for a Girl in Buchannon." Most people recognize the hits plucked from it—"Make Me Smile" and "Colour My World"—but listening to them as isolated radio edits is like looking at a single corner of a Picasso painting. The full 13-minute suite is a seamless transition of moods. James Pankow, the trombonist who wrote it, was trying to bring classical structure into a rock context.
- Make Me Smile: The energetic opening.
- So Much to Say, So Much to Give: A gentle, melodic bridge.
- Anxiety's Moment: An instrumental that feels exactly like its title.
- West Virginia Fantasies: Intricate, interlocking horn parts.
- Colour My World: The slow-dance classic that everyone knows.
"Colour My World" is basically the most overplayed song in history, but in the context of the suite, it actually works. It provides a moment of stillness after the technical gymnastics of the instrumental sections.
The Political Edge People Forget
It’s easy to think of Chicago as "safe" music now. It's the music your parents play while grilling. But in 1969 and 1971, they were deeply embedded in the counter-culture.
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"Dialogue (Part I & II)" from Chicago V is a literal conversation between two people with different political views. One is a social activist, and the other is a college student who just wants to "take it easy" and ignore the world's problems. It’s surprisingly relevant today. Then you have "It Better End Soon," a multi-part epic about the Vietnam War. They weren't just playing pretty melodies; they were using that massive wall of brass to scream at the establishment.
Robert Lamm, the keyboardist and one of their primary songwriters, was the architect of this socially conscious side. His songs often had a breezy, Latin-influenced groove that masked some pretty heavy lyrics. Take "Saturday in the Park." It’s arguably their most famous song. People think of it as a happy anthem about a nice day. But listen closer. "Can you dig it? Yes, I can!" was a direct nod to the Black Power movement and the slang of the era. It was about a moment of racial and social harmony in a time when the country was tearing itself apart.
The Great 80s Pivot: Love It or Hate It
By the time the 1980s rolled around, the band was in trouble. Their jazz-rock fusion was falling out of favor. Enter David Foster.
Foster is a polarizing figure for Chicago fans. On one hand, he saved their career. He turned them into one of the biggest acts in the world again with Chicago 16, 17, and 18. On the other hand, he sidelined the horn section—the very thing that made them unique—in favor of synthesizers and Peter Cetera’s tenor.
If you look at a songs by chicago list from this era, it’s a string of number one hits:
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- "Hard to Say I'm Sorry" (1982)
- "You're the Inspiration" (1984)
- "Will You Still Love Me?" (1986)
- "Look Away" (1988)
"Look Away" is a weird one. It was the most-played song of 1989. It was written by Diane Warren, not the band. It features almost no horns. For many "Old Chicago" purists, this was the end of the road. It was good pop music, sure, but it wasn't Chicago. It sounded like any other power ballad of the late 80s. Yet, you can't argue with the numbers. These songs kept the lights on for decades.
Why "25 or 6 to 4" Still Rules
We have to talk about the title. For years, people thought it was a drug reference or some secret code. It’s actually just about songwriting. Robert Lamm was sitting at his piano, trying to finish the song, and he looked at his watch. It was twenty-five or twenty-six minutes until four o’clock in the morning.
The song is a masterpiece of tension and release. The descending bassline is one of the most recognizable in rock history. But the real genius is how the horns punctuate the beat. Instead of just playing long, melodic lines, they act like a percussion section. They hit these sharp, staccato notes that drive the energy forward.
There are very few songs from 1970 that still sound that modern. It’s been covered by everyone from metal bands to marching bands. It’s the definitive proof that Chicago was, at its core, a rock band that just happened to have a lot of brass.
Practical Steps for Exploring Their Discography
If you're tired of the same three ballads and want to actually hear why this band matters, don't just shuffle a "Best Of" collection. Most of those are weighted heavily toward the 80s because that’s what sells. Instead, try this:
- Listen to 'Chicago Authority' (the first album) from start to finish. It’s raw, it’s live-sounding, and it’s unapologetically loud. Pay attention to "South California Purples."
- Watch the Tanglewood 1970 live performance. It’s on YouTube. You’ll see Terry Kath in his prime, and it will completely change your perception of what this band was capable of on stage.
- Dig into 'Chicago VII'. This is their most experimental album. It’s a double album where the first half is almost entirely instrumental jazz-fusion. It was a huge risk, and it’s some of their most rewarding work.
- Compare the vocalists. Chicago was unique because they had three distinct lead singers: Robert Lamm (the smooth baritone), Terry Kath (the soulful growler), and Peter Cetera (the high tenor). Tracking which singer handles which song gives you a much deeper appreciation for their range.
- Look for the deep cuts. Songs like "Questions 67 and 68" (especially the Japanese version) or "A Hit by Varese" show a band that was obsessed with the mechanics of music, not just the charts.
The evolution of Chicago is a fascinating study in the tension between artistic ambition and commercial reality. They started as rebels and ended as icons of the mainstream. Somewhere in between, they created a body of work that is far more diverse than the average radio listener realizes. Whether you're there for the 13-minute suites or the three-minute ballads, there's a version of Chicago that fits your mood. Just make sure you give the horn section the respect they deserve. They've been working hard for over fifty years.