The task of choosing just five songs from Chicago’s vast catalog is tough. Really tough. However, that’s why I limited the choice to five, to make the selection a hard one. The five songs that I pick probably won’t be somebody else’s five.
Chicago wasn’t the first rock band to have horns, but they were perhaps the most successful to integrate horns into, and a prominent part of their sound.
Jazz, R&B and classical were blended into their songwriting, and on full display on their early albums. Their first three albums were double albums, giving the band plenty of room to stretch musically.
Giddy up!
“Beginnings” (1969) From Chicago Transit Authority – The debut album shows the band’s different sounds, this was a group with jazz, R&B and hard rockin’ roots. The rhythmic backbone of this song shows what a great rhythm section Chicago had. This song melodic and hypnotic.
“Does Anybody Really Know What Time It Is?” (1969) From Chicago Transit Authority – This film clip is a live performance of the band performing the song, a nine minute version. I always love this song and any doubt that horns were just decoration should listen to how important they are in the arrangement. Another song penned by Robert Lamm, who in the beginning was the main songwriter. His voice may not have the instant recognition of Peter Cetera’s, but it an earthier, rock and roll vocal.
“Saturday in the Park” (1972) From Chicago V – There are other Chicago songs I like better, but this song is a good one. “Dialogue (Part I & II)” is a more defining song from the album, it definitely has a strong message, something the band moved away from. Written by Lamm, with lead vocals shared by him and Cetera on what is referred to as a “sunshine pop” rocker, whatever that means. The song is upbeat with bright imagery, not a bad thing in 1972.
“Wishin’ You Were Here” (1974) From Chicago VII – Back to the double album format, Chicago VII was a big commercial seller. This album is notable for percussionist Laudir de Oliveira, who became a band member. This was a platinum selling and number one charting album. The album alternates between smooth Beach Boys ballads and smooth jazz, not a lot of rock and roll in sight. “Wishin’ You Were Here” was written by Cetera and sung by Cetera and Terry Kath. This song is exactly what I began to despise about Chicago.
“Old Days” (1975) From Chicago VIII – A nice rocker, another great track by Jim Pankow, who was had been a key songwriter, but was getting the singles along with Cetera. Lamm was contributing less material as others in the band were stepping up. “Old Days” is sung by Cetera, who was becoming the face and voice of the band. The song’s arrangement showcases the strengths of the band, with horns that drive the song and several great guitar fills by Kath. This song was the closer on the album, a somewhat bittersweet moment, as Chicago would never quite sound like this period again.
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Are these the five “best” songs by a band in their sixth decade? I ignored the David Foster years where the band enjoyed renewed chart success because I don’t care much for that period or the output. Chicago XI (1977) and Hot Streets (1978) both featured some great material and were a bit uncharacteristic for a band seems to be swimming against the changing musical currents of the era. The loss of guitarist Terry Kath permanently changed Chicago in many important ways.






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