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* CreatorBacklash: He thinks of "The Boxer" as a failure as he couldn't think of any lyrics for several lines and just threw in a generic "Lie la lie" over all of them.

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* CreatorBacklash: He thinks While he loves the song itself (it's his favorite of his career with Garfunkel along with "Bridge over Troubled Water" and "The Sound of Silence"), he states about "The Boxer" as a failure as that he couldn't think of any lyrics for several lines and just threw in a generic "Lie la lie" over all of them.them, considering this a failure.
** Played straight with "The 59th Street Bridge Song", which he stated to hate.
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* WhatCouldHaveBeen: He was approached to participate on the ProtestSong ''Sun City'' by Artists United Against Apartheid, but he declined due to feeling that the song's original plan of directly referecing artists who have played in the titular resort was inappropriate and didn't give the artists a chance to admit they were wrong. The idea ended up being omitted from the final version.

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* WhatCouldHaveBeen: He was approached to participate on the ProtestSong ''Sun City'' by Artists United Against Apartheid, but he declined due to feeling that the song's original plan of directly referecing referencing artists who have played in the titular resort was inappropriate and didn't give the artists a chance to admit they were wrong. The idea ended up being omitted from the final version.
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* BreakawayPopHit: His semi-autobiographical film ''Film/OneTrickPony'' was a box-office bomb, but the song "Late in the Evening" made it to #6 on Billboard's Hot 100.
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* WhatCouldHaveBeen: He was approached to participate on the ProtestSong ''Sun City'' by Artists United Against Apartheid, but he declined due to feeling that the song's original plan of directly referecing artists who have played in the titular resort was inappropriate and didn't give the artists a chance to admit they were wrong. The idea ended up being omitted from the final version.
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* InspirationForTheWork: Simon got the title for "Mother and Child Reunion" from the name of a chicken-and-egg dish at a New York Chinese restaurant. Musically he drew inspiration from early {{Reggae}} star Jimmy Cliff, particularly his ProtestSong "Vietnam"; Simon even went to Jamaica and enlisted Cliff's backing band to record the song's basic track. The lyrics were written while Simon was going through the grieving process after his dog was killed by a car.

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* InspirationForTheWork: Simon got the title for "Mother and Child Reunion" from the name of a chicken-and-egg dish at a New York Chinese restaurant. Musically he drew inspiration from early {{Reggae}} star Jimmy Cliff, particularly his ProtestSong "Vietnam"; "Vietnam" (which is similarly [[LyricalDissonance an upbeat song with heartbreaking lyrics]]); Simon even went to Jamaica and enlisted Cliff's backing band to record the song's basic track. The lyrics were written while Simon was going through the grieving process after his dog was killed by a car.
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* InspirationForTheWork: Simon got the title for "Mother and Child Reunion" from the name of a chicken-and-egg dish at a New York Chinese restaurant. Musically he drew inspiration from early {{Reggae}} star Jimmy Cliff, particularly his ProtestSong "Vietnam"; Simon even went to Jamaica and enlisted Cliff's backing band to record the song's basic track. The lyrics were written while Simon was going through the grieving process after his dog was killed by a car.
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* ChannelHop:
** After over a decade as one of the core artists for Creator/ColumbiaRecords, Simon clashed with Columbia president Walter Yetnikoff in the latter part of TheSeventies, insisting that the label was cheating him on royalties. Ultimately, Simon ponied up a huge amount of money to buy out his contract, and moved to Creator/WarnerBrosRecords in 1980. He stayed there for three decades.
** With ''So Beautiful or So What'' in 2011 he moved to Concord Music Group for his next two albums, and 2018's ''In the Blue Light'' saw him return to Columbia's current parent company, Creator/{{Sony}}.
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* CreatorBacklash: He thinks of "The Boxer" as a failure as he couldn't think of any lyrics for several lines and just threw in a generic "Lie la lie" over all of them.
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* ShrugOfGod: He's repeatedly stated he doesn't know himself what the crime is in "Me and Julio Down by the Schoolyard." The most he's ever specified is that it's "something sexual, I imagine."
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* TechnologyMarchesOn: "Kodachrome" (1973) refers to the first successfully mass-marketed color still film, comparing it to memories. These days digital photography has taken over, and the name "Kodachrome" is more connected to the song than the film. The last batch of actual Kodachrome film was shipped out in 2009 with an expiration date of November 2010.

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* TechnologyMarchesOn: "Kodachrome" (1973) refers to the first successfully mass-marketed color still film, comparing it to memories. These days digital photography has taken over, and the name "Kodachrome" is more connected to the song than the film. The last batch of actual Kodachrome film was shipped out in 2009 with an expiration date of November 2010.2010.
* WriteWhoYouKnow: Both "Graceland" and "Hearts and Bones" were inspired by Simon's ill-fated marriage to Creator/CarrieFisher.
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* TechnologyMarchesOn: "Kodachrome" (1973) refers to the first successfully mass-marketed color still film, comparing it to memories. These days digital photography has taken over, and the name "Kodachrome" is more connected to the song than the film. The last batch of actual Kodachrome film was shipped out in 2009 with an expiration date of November 2010.

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