Hard Habit to Break: A Look at Chicago’s Best Songs

4. Make Me Smile

Their self-titled album was considered by many as the band’s breakthrough record. It produced a number of Top 40 hits, one of which was Make Me Smile. This was the band’s first single to hit the Top Ten, reaching number nine in the Billboard Hot 100 in 1970. The song was actually the first part of the album’s centerpiece, a 13-minute track called Ballet for A Girl in Buchannon.

3. Hard to Say I’m Sorry

The Chicago 16 album, which was released in 1982, featured a different sound from the band. They ditched their more jazz-influenced and horn-driven sound in the 70s and instead opted for more distorted electric guitars as what was popular in the 80s. The 80s were a weird time and here we see Chicago journeying towards powerballad territory. The band was considered past their commercial prime at this point. Along with You’re The Inspiration, this was one of the tracks that helped revitalize Chicago’s career. And with that, the song became a pop classic, becoming a mainstay in classic rock radios and in the many taxis that you’ve ridden.

2. Love Me Tomorrow

Love Me Tomorrow once again sees Chicago in ballad form. It’s sad proof that they’ve done away with the eclectic sound which made them in the 70s. However, this track is undeniably powerful. Peter Cetera’s vocals are a thing to behold here and are paired perfectly with a soft rock melody.

1. 25 or 6 to 4

With their transition to powerballads, most people forget how Chicago used to be a kickass rock and roll band. 25 or 6 to 4 serves as the exclamation point to this statement. It featured a powerful and aggressive blaring horn section, and also showed one of the greatest guitar riffs of all time–further defining Terry Kath as an underrated guitar player, if not a bonafide guitar hero/god. He was more than capable of shredding some face-melting and mind-blowing licks, as shown in the video above. This track shows how much Chicago is still a force to be reckoned with.

What are your favorite Chicago songs of all time? Sound off in the comments section!