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1* CoveredUp: "And I Love You So" is one of his songs, but has been covered by Elvis and was a hit for Perry Como. In reverse, [=McLean=]'s "Crying," a huge hit, was originally performed by Roy Orbison.
2* EveryoneIsJesusInPurgatory: "American Pie" is about the plane crash that killed Music/BuddyHolly, Music/RitchieValens, and Music/TheBigBopper. That much has been confirmed. The rest of the lyrics have been much-discussed as being an extended metaphor about the evolution of {{Rock}}, with many guesses as to the identities of the names and places. The King (Music/ElvisPresley), The Jester (Music/BobDylan) and The Marching Band (Music/TheBeatles) were widely agreed-upon, but [=McLean=] {{Jossed}} all those in 2022 in the Creator/ParamountPlus documentary ''The Day the Music Died: The Story of Don [=McLean=]'s American Pie'';[[note]]Presley's not "the king" in question, Dylan is not "the jester" (as the man himself already predicted in 2017)--and the marching band actually means the military–industrial complex.[[/note]] many of the others are still disputed. Reportedly, years prior to said documentary, when [=McLean=] himself was asked about it, he replied "What is the meaning of 'American Pie'? [[MathematiciansAnswer It means I never have to work again]]."
3* SugarWiki/FunnyMoments: If one doesn't pay attention to the [[EveryoneIsJesusInPurgatory disputed symbolism]] and takes the lyrics literally, what happens with the Jester in "American Pie" can come off as a BrickJoke. First he steals the King's crown while performing for him, the court failing to convict him for it... then a verse later, during a football game, the same Jester is on the sidelines in a cast. [[KarmaHoudiniWarranty Apparently he didn't get away with the theft as much as he thought]].
4* GeniusBonus: Several. "American Pie" contains references to events and people who were notable in [=McLean's=] childhood. Furthermore, "the Levee" is not a levee, but a bar (giving the phrase "but the Levee was dry" an entirely new meaning).
5* GermansLoveDavidHasselhoff - "Crying" and "Vincent" did much better in the UK, both reaching #1 (in fact they did ''better'' than "American Pie" which reached #2). The parent album of "Crying", ''Chain Lightning'', [[ShortRunInPeru was released in Europe]] almost three years before it came out in America, and it was the #1 success of "Crying" in the UK that prompted the song and album to finally get an American release.
6* NightmareFuel: The penultimate verse of "American Pie" obliquely but hauntingly references the murder of Meredith Hunter at a Music/{{The Rolling Stones|Band}} concert, with the narrator saying "[he] saw Satan laughing with delight" at the killing.
7* ParodyDisplacement: His kids were such big fans of Music/WeirdAlYankovic and have played "The Saga Begins" so much, that even Don has mixed up some of the lyrics of "American Pie" with the parody while performing it.
8* RefrainFromAssuming:
9** There are some people who know "American Pie" as "The Day the Music Died".
10** Also, the song "Vincent" is ''not'' "Starry Starry Night".
11* SecondVerseCurse: Because "American Pie" was so long, it was released originally on a dual-sided single. Some radios only played Part One.
12* SignatureSong: "American Pie", a melancholic masterpiece explaining the history of rock-n-roll ever since the deaths of Buddy Holly, Ritchie Valens and The Big Bopper with tons of metaphors and comparisons for anyone to ponder over and make comparisons to real life events.
13* ToughActToFollow: ''Music/AmericanPie'' was a commercial and critical success, but he never managed to duplicate it.

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