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  • Breakaway Pop Hit: His semi-autobiographical film One-Trick Pony was a box-office bomb, but the song "Late in the Evening" made it to #6 on Billboard's Hot 100.
  • Channel Hop:
    • After over a decade as one of the core artists for Columbia Records, Simon clashed with Columbia president Walter Yetnikoff in the latter part of The '70s, 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 Warner (Bros.) Records 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, Sony.
  • Creator Backlash: 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" that he couldn't think of any lyrics for several lines and just threw in a generic "Lie la lie" over all of them, considering this a failure.
    • Played straight with "The 59th Street Bridge Song", which he stated to hate.
  • Inspiration for the Work: 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 Protest Song "Vietnam" (which is similarly 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.
  • Shrug of God: 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."
  • Technology Marches On: "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.
  • What Could Have Been: He was approached to participate on the Protest Song Sun City by Artists United Against Apartheid, but he declined due to feeling that the song's original plan of directly 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.
  • Write Who You Know: Both "Graceland" and "Hearts and Bones" were inspired by Simon's ill-fated marriage to Carrie Fisher.

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