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  • Accidental Innuendo: Before they even became the Chicago Transit Authority, they went by the name "The Big Thing", which apparently caused some controversy in the Chicago club circuit (they were forced to perform in some clubs as "The Big Sound").
  • Awesome Music: Progressive Rock and jazz-rock fans will find the first three albums to be a veritable goldmine, as well as (probably) quite a lot of Chicago VII. Steven Wilson (of Porcupine Tree fame) remixed the second album, in case you needed more evidence of their prog cred.
  • Broken Base: Their stuff post-Kath era divides the fanbase, especially the 80's "power ballad" era.
  • Critical Dissonance: Their first album garnered positive reviews, but overall, they were never the darlings of the music press.
  • Early-Installment Weirdness: Robert Lamm's Author Tracts on the first few albums. Hearing Peter Cetera of all people singing about the need to "tear the system down to the ground" on Chicago V can be a bit jarring for younger listeners.
  • Epic Riff: "25 or 6 to 4".
  • First Installment Wins: As far as critics are concerned with their first album (see Critical Dissonance above).
  • Harsher in Hindsight: The inside gatefold photo of their eleventh album, which was released in November 1977, features the band, in an antique car, being chased by a group of policemen (some of whom are firing guns) in another car. One of the guns seems pointed at the head of Terry Kath, who is driving the band’s car. In January 1978, Kath died of an accidental, self-inflicted gunshot wound to the head.
  • Memetic Mutation: Cock and ball tortureExplanation 
  • Narm: The bridge of "Stay the Night." The last line leading into the guitar solo has Peter grunting, "We're gonna have a very good time!" as if it's the most important thing he's ever said.
  • Replacement Scrappy: Kath replacement Donnie Dacus lasted for only two albums (Hot Streets and Chicago XIII), and was later acknowledged as "a mistake".
    • Jason Scheff for Peter Cetera fans.
    • Tris Imboden, who replaced founding drummer Danny Seraphine in 1990. Doesn't help the fact that Seraphine's departure remains the most controversial in history of the band, with differing sources claimed either he quit or he got fired.note 
    • Unfortunately, this goes for any lead vocalist whose name isn't Terry Kath, although Peter Cetera and Bill Champlin avert this.
  • Signature Song: Depending on whom you ask, "25 or 6 to 4", "Saturday in the Park", or "Hard to Say I'm Sorry".
    • Following the release of Elite Beat Agents, "You're the Inspiration" has joined the list.
    • "If You Leave Me Now" is another contender.
  • Sampled Up: "Street Player" from Chicago 13 bombed when released as a single, but was very successful as a sample for "The Bomb" by the Bucketheads and Pitbull's "I Know You Want Me (Calle Ocho)".
  • Song Association:
    • Although "You're the Inspiration" is actually a pretty standard love song, both musically and lyrically, it's gained a reputation for being a very powerful musical Tear Jerker thanks to its use in Elite Beat Agents, where it plays during a level where you help a little girl grieve her dead father. Those who've played this game might find themselves getting misty-eyed whenever they hear that song.
    • After being memetically mashed up with a reading of the Wikipedia article for cock and ball torture, the song "Old Days" is almost exclusively associated with the latter by netizens.
  • Tear Jerker:
    • "Little One", from their eleventh album, features Terry Kath on lead vocals and was a minor hit shortly after his death in early 1978. Although it was written by drummer Danny Seraphine for his two girls, Terry clearly sang it with his own toddler daughter in mind. One might get the feeling that he somehow knew he wasn't going to be around to see her grow up.
    • "If You Leave Me Now" is quite a sad one, not helped by the somber instrumentals and the fact that they also used in a fund raiser with the American Cancer Society, for breast cancer awareness.
    The love like ours is love that's hard to find
    How could we let it slip away?
    We've come too far to leave it all behind
    How could we end this all this way
    When tomorrow comes and we'll both regret
    The things we've said today
    • Walter Parazaider’s announcement in April 2021 that he has been diagnosed with Alzheimer’s disease.
  • They Changed It, Now It Sucks!: Their '70s fans cried this when they started focusing more on soft rock ballads in the '80s.

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