->''"Bye-bye, Miss American Pie..."''

By far best known for "American Pie" (which was voted Number 5 of the 365 Songs of the Century by the Recording Industry Association of America and the National Endowment for the Arts), Don [=McLean=] is an influential folk-rock singer/songwriter. He reached the height of his success in the 70s with his album, ''American Pie'', which contained the titular hit as well as the other notable single, "Vincent."

"American Pie" was written in memory of Music/BuddyHolly, Ritchie Valens, and The Big Bopper, who were killed in a plane crash in 1959. The song popularized the phrase "The Day the Music Died" in reference to the event. The lyrics also reflect the impact that event had on [=McLean's=] childhood and the song is semi-autobiographical in nature. It reached number one on the charts for four weeks in 1972 and holds the record for the longest song to occupy that slot, with a run time of 8 minutes 36 seconds (though only half the song was on the A-side; the other half was on the B-side).

After "American Pie," [=McLean=] continued to write and perform songs. He found further success in the UK, but never again saw such popularity in the States. He is known for covering the songs of Music/BuddyHolly, for obvious reasons, and also Music/RoyOrbison--his substantial vocal range fits Orbison's repertoire well.
!!He/His work contains examples of:

* AmericanTitle: "American Pie"
* BlackSheepHit: "American Pie", which effectively dogged his career because everyone wanted him to write another song just like "American Pie".
* CreatorBacklash: "American Pie", not just for the fact that it's overshadowed his other songs tremendously, but also [=McLean=]'s eternal annoyance at constantly being asked what the song means.
** So much so that part of [=McLean's=] contract stipulates that any advertising must list at least five other songs of his if they want to tout "American Pie". How many songs of [=McLean's=] do you know?
* GoMadFromTheRevelation: Similar to the Total Perspective Vortex from ''Franchise/TheHitchhikersGuideToTheGalaxy'', "Infinity" appears to be about being confronted by the [[InsignificantLittleBluePlanet smallness of Earth in the universe]].
* GriefSong: "American Pie" for the three victims of The Day the Music Died, and "Vincent" for Creator/VincentVanGogh and "The Grave" for the unnamed soldier and his comrades.
* IAmGreatSong: "Everybody Loves Me, Baby"
* IntelligenceEqualsIsolation: "Vincent"
* LastChorusSlowDown: The final verse of "American Pie".
* LyricalColdOpen: "American Pie"
* LyricalDissonance: "Primetime"
** Also "Have You Seen Me?", which is a rollicking number about... child soldiers.
* MoralityBallad: "American Pie," sort of.
* OneHitWonder: While "Vincent" and "Crying" both reached the top twenty on the American charts, "American Pie" was his only number one and the song he is most famous for.
* RearrangeTheSong: Music/{{Madonna}}'s version of "American Pie" took a few liberties, to say the least. [=McLean=] himself gave it a positive review, however, saying that the album's cover was "a gift from a goddess", and that her version was "mystical and sensual".
** [=McLean=] himself did this with his own "Castles in the Air", and wound up having a much bigger hit with the remake.
* RefrainFromAssuming: There are some people who know "American Pie" as "The Day the Music Died".
** Also, the song "Vincent" is ''not'' "Starry Starry Night".
* SomewhereSong: "Castles in the Air"
* TeenageDeathSongs: "The Grave", about a young Marine dying in the UsefulNotes/VietnamWar.
* ThreeChordsAndTheTruth
* TitledAfterTheSong: ''Film/AmericanPie''
* TheWalrusWasPaul: On the subject of "American Pie," the only concrete explanation [=McLean=] has ever given is that it means he'll never have to work again.
** He has admitted that the line "February made me shiver/with every paper I'd deliver" was about him learning about the deaths of Buddy Holly, The Big Bopper, and Ritchie Valens while he was folding papers for his paper route.
* WordSaladLyrics: "American Pie"
->''"This will be the day that I died."''