- Covered Up: "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.
- Everyone Is Jesus in Purgatory: "American Pie" is about the plane crash that killed Buddy Holly, Ritchie Valens, and The Big Bopper. 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 (Elvis Presley), The Jester (Bob Dylan) and The Marching Band (The Beatles) seem to be widely agreed-upon, but many of the others are still disputed. Reportedly when McLean himself was asked about it, he replied "What is the meaning of 'American Pie'? It means I never have to work again."
- Genius Bonus: 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).
- Germans Love David Hasselhoff - "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, 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.
- Nightmare Fuel: The penultimate verse of "American Pie" obliquely but hauntingly references the murder of Meredith Hunter at a Rolling Stones concert, with the narrator saying "[he] saw Satan laughing with delight" at the killing.
- Second Verse Curse: Because "American Pie" was so long, it was released originally on a dual-sided single. Some radios only played Part One.
- Signature Song: "American Pie", full stop.
- Tough Act to Follow: American Pie was a commercial and critical success, but he never managed to duplicate it.
- "Weird Al" Effect: His kids were such big fans of "Weird Al" Yankovic 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.
- To a lesser extent, Madonna's cover was this after Weird Al's parody, with lots of fans asking why Madonna was singing an unfunny version of a Weird Al song.
YMMV / Don McLean