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* EarlyInstallmentWeirdness: Robert Lamm's {{Author Tract}}s 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.

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* EarlyInstallmentWeirdness: Robert Lamm's {{Author Tract}}s 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" ''Chicago V'' can be a bit jarring for younger listeners.
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* EarlyInstallmentWeirdness: Robert Lamm's {{Author Tract}}s on the first few albums. Hearing Peter Cetera of all people singing about the need to "tear the system down" can be a bit jarring for younger listeners.

to:

* EarlyInstallmentWeirdness: Robert Lamm's {{Author Tract}}s on the first few albums. Hearing Peter Cetera of all people singing about the need to "tear the system down" down to the ground" on "Chicago V" can be a bit jarring for younger listeners.
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** Walter Parazaider’s announcement in April 2021 that he has been diagnosed with Alzheimer’s disease.
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* MemeticMutation: Cock and ball torture[[labelnote:Explanation]]An audio reading of the Website/{{Wikipedia}} article for the eponymous GroinAttack fetish, underscored by "Old Days". The audio became a common subject for bait-and-switch jokes and resulted in uploads of "Old Days" being met with constant references to the fetish.[[/labelnote]]
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* FaceOfTheBand: Averted for a while, then in TheEighties, it was Peter Cetera. Who then left halfway through the decade.
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* HarsherInHindsight: 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.

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* HarsherInHindsight: 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 policemen (some of whom are firing guns)in 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.
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* FirstInstallmentWins: As far as critics are concerned with their first album (see CriticalDissonance above).

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* TearJerker: "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.

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* TearJerker: TearJerker:
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"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.



* TheyChangedItNowItSucks: Their '70s fans cried this when they started focusing more on soft rock ballads in the '80s.

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* TheyChangedItNowItSucks: Their '70s fans cried this when they started focusing more on soft rock ballads in the '80s.'80s.
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** After being memetically mashed up with a reading of the Wiki/{{Wikipedia}} article for [[GroinAttack cock and ball torture]], the song "Old Days" is almost exclusively associated with the latter by netizens.

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** After being memetically mashed up with a reading of the Wiki/{{Wikipedia}} Website/{{Wikipedia}} article for [[GroinAttack cock and ball torture]], the song "Old Days" is almost exclusively associated with the latter by netizens.
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* FunnyAneurysmMoment: 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.

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* FunnyAneurysmMoment: HarsherInHindsight: 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.
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* SugarWiki/AwesomeMusic: ProgressiveRock 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''. Music/StevenWilson (of Music/PorcupineTree fame) recently remixed the second album, in case you needed more evidence of their prog cred.

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* SugarWiki/AwesomeMusic: ProgressiveRock 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''. Music/StevenWilson (of Music/PorcupineTree fame) recently remixed the second album, in case you needed more evidence of their prog cred.
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* SampledUp: "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 Music/{{Pitbull}}'s "I Know You Want Me (Calle Ocho)".
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* AccidentalInnuendo: 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").
* SugarWiki/AwesomeMusic: ProgressiveRock 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''. Music/StevenWilson (of Music/PorcupineTree fame) recently remixed the second album, in case you needed more evidence of their prog cred.
* BrokenBase: Their stuff post-Kath era divides the fanbase, especially the 80's "power ballad" era.
* CriticalDissonance: Their first album garnered positive reviews, but overall, they were never the darlings of the music press.
* EarlyInstallmentWeirdness: Robert Lamm's {{Author Tract}}s on the first few albums. Hearing Peter Cetera of all people singing about the need to "tear the system down" can be a bit jarring for younger listeners.
* EpicRiff: "25 or 6 to 4".
* FaceOfTheBand: Averted for a while, then in TheEighties, it was Peter Cetera. Who then left halfway through the decade.
* FunnyAneurysmMoment: 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.
* {{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.
* ReplacementScrappy: 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]]Why Seraphine may have been fired is a story of itself. One source said Seraphine became too enamored with electric drum machines and started performing poorly live. Others say Seraphine became too involved with the business side of the band. Seraphine noted in his autobiography he used to have a short temper, with an example being an incident where he got into a fist fight with his drum tech during a sound check and the tech quit his job on the spot, leading to another story where rumors had it that Seraphine attacked the band's manager backstage after a show due to a small misunderstanding on the manager's part. Later that night, Seraphine was traveling on a plane and the manager's brother asked why he attacked the manager. Seraphine supposedly lost it again and attacked the brother. The brother later died from a "heart attack", although some think Seraphine's attack had something to do with it.[[/note]]
** Unfortunately, this goes for any lead vocalist whose name isn't Terry Kath, although Peter Cetera and Bill Champlin avert this.
* SignatureSong: 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 ''VideoGame/EliteBeatAgents'', "You're the Inspiration" has joined the list.
** "If You Leave Me Now" is another contender.
* SongAssociation:
** 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 TearJerker thanks to its use in ''VideoGame/EliteBeatAgents'', 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 Wiki/{{Wikipedia}} article for [[GroinAttack cock and ball torture]], the song "Old Days" is almost exclusively associated with the latter by netizens.
* TearJerker: "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
* TheyChangedItNowItSucks: Their '70s fans cried this when they started focusing more on soft rock ballads in the '80s.

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