How Does 24 or 5 Chicago Songs Sound?

8.1 Chicago 1970

Looking back over the music of the Seventies, you pretty much have to admit that the decade was pretty eclectic. See, we had heavy metal, arena rock, bubble gum, power pop, new wave, punk, post-punk, shock rock, glam, acid rock, disco, soul, country rock, southern rock, outlaw country, progressive or art rock, pop, adult contemporary, soft rock (now known as “yacht rock”), funk and whatever the hell Frank Zappa was doing. Rock ‘n’ roll, as an art form, had begun in earnest in the mid-Fifties, so by the mid-Seventies, it was twenty years old. Enough time had passed, with the form being so accommodating to other sounds that musicians were all able to follow their muse wherever it took them. So, genres and sub-genres of rock music began to spring up as fast as people could label and define them. In other words, the rock music canvas was relatively clear, and it was time to paint.

That’s why the music by diverse artists such as Billy Joel, Captain and Tennille, Grand Funk, Village People, Al Green, ABBA, Black Sabbath and Don McLean could all co-exist on a radio  playlist with nary a thought given by the listener. Crazy times! And, I am NOT touching the fashion statements we made throughout that decade. So, should we have been surprised to when we discovered that a band who fused jazz and rock music were the leading singles charting band in the States throughout the Seventies. The band, who originally went by the moniker Chicago Transit Authority, but quickly shortened to Chicago were the very band. This band sold over 40 million records, earning 23 gold, 18 platinum and eight multi-platinum albums along the way. At one point in the Seventies, Chicago had five consecutive number one albums. The band also had 20 songs hit the Top 10 on Billboard‘s Hot 100 Singles.

Chicago formed in 1967, while the members were all students at DePaul University in their namesake city. The original lineup consisted of bassist/singer Peter Cetera, guitarist/singer Terry Kath (who was Jimi Hendrix favorite guitarist!), keyboardist/singer Robert Lamm (the only one not from DePaul), trumpeter Lee Loughnane, trombonist James Pankow, saxophonist Walter Parazaider, and drummer Danny Seraphine, with Cetera, Lamm and Pankow handling the songwriting, while Kath was the musical leader.

8.1 Chicago IX

Since Chicago was more successfully integrating jazz textures and song structures within pop songs than bands such as Electric Flag and Blood, Sweat & Tears, high school band teachers were excited to exposed their budding musicians to Chicago’s music. During the Seventies, there was nary a high school pep band that did not play Chicago during an Indiana football or basketball game.

Unfortunately, the band began to suffer creatively after Terry Kath died due to a self-inflicted gunshot wound to his head while he played around with his gun. Thus began frequent lineup changes, Peter Cetera’s ascent to the leadership role, his subsequent departure and their continued mindset to carry on not only as a touring band but as a recording band as well. As the years passed, the band’s career has been re-evaluated, leading to their 2016 induction into the Rock and Roll Hall of Fame, as well as Cetera, Lamm and Pankow being inducted into the Songwriters’ Hall of Fame.


Personally, I prefer the pre-Kath’s death music, but the band did stage a nice comeback during the years 1982 through 1985, riding several hit songs into the Top 10. But, the band could never replace the devastating guitar work that Kath brought to the band. My suggestion is to go back and listen to their cover of the Spencer Davis Group’s hit song “I’m a Man.” Kath shreds throughout the song like a man possessed, making the song Chicago’s in the process. Plus, his unique vocals could never be duplicated by anyone. Creatively, his loss hurt the most, as Chicago slid successfully into one of the best ballad artists this side of Lionel Richie. Unfortunately, without Kath, Chicago became a soft rock act.

Today, I would like to present my Top 25 Songs by Chicago. When it comes to Chicago, I am more of a hits man than a deep cuts admirer. Still, I feel you will find some of my top songs surprising. Full disclosure: I will be seeing Chicago and REO Speedwagon, which, outside of their Illinois connection, seems like a weird partnership, except maybe for the number of ballads we may be hit with during the concert. On with the countdown!

8.1 Chicago - Hard Habit to Break

25. “Hard Habit to Break” (1984)

24. “Love Me Tomorrow” (1982)

23. “Stay the Night” (1984)

22. “If You Leave Me Now” (1976)

21. “Along Comes a Woman” (1985)

20. “Just You ‘n’ Me” (1973)

8.1 Chicago - Harry Truman

19. “Harry Truman” (1975)

18. “Free” (1970)

17. “No Tell Lover” (1978)

16. “(I’ve Been) Searchin’ So Long” (1973)

15. “Does Anybody Really Know What Time It Is?” (1970)

14. “25 or 6 to 4” (1970)

13. “Questions 67 and 68” (1970)

12. “Beginnings” (1969)

11. “Hard to Say I’m Sorry” (1982)

8.1 Chicago - Alive Again

10. “Alive Again” (1978)

8.1 Chicago - Color My World

9. “Colour My World” (1971)

8. “Wishing You Were Here” (1974)

7. “Make Me Smile” (1970)

6. “Baby What a Big Surprise” (1977)

5. “Feelin’ Stronger Every Day” (1973)

4. “I’m a Man” (1969)

3. “Saturday in the Park” (1972)

8.1 Chicago - Old Days

2. “Old Days” (1975)

8.1 Chicago - The Very Best of Chicago - Only the Beginnings 2002

1. “Dialogue Parts 1 & 2” (1972)

8.1 Chicago 2018

And, there you go! My 25 favorite songs by Chicago. Let the arguing begin!

Author: ifmyalbumscouldtalk

I am just a long-time music fan who used to be a high school science teacher and a varsity coach of several high school athletic teams. Before that, I worked as a medical technologist at three hospitals in their labs, mainly as a microbiologist. I am retired/disabled (Failed Back Surgery Syndrome), and this is my attempt to remain a human. Additionally, I am a serious vinyl aficionado, with a CD addiction and a love of reading about rock history. Finally, I am a fan of Prince, Cheap Trick, Tom Petty, R.E.M., Hall & Oates, Springsteen, Paul Weller & his bands and Power Pop music.

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