According to McLean (as posted on his website), this song was originally inspired by the death of Buddy Holly. "The Day The Music Died" is February 3, 1959, when Holly, Ritchie Valens, and The Big Bopper were killed in a plane crash after a concert. McLean wrote the song from his memories of the event ("Dedicated to Buddy Holly" was printed on the back of the album cover). The Beatles Sgt. Pepper album was also a huge influence, and McLean has said in numerous interviews that the song represented the turn from innocence of the '50s to the darker, more volatile times of the '60s - both in music and politics.
Talking about how he composed this song when he was a guest on the UK show Songbook, McLean explained: "For some reason I wanted to write a big song about America and about politics, but I wanted to do it in a different way. As I was fiddling around, I started singing this thing about the Buddy Holly crash, the thing that came out (singing), 'Long, long time ago, I can still remember how that music used to make me smile.'
I thought, Whoa, what's that? And then the day the music died, it just came out. And I said, Oh, that is such a great idea. And so that's all I had. And then I thought, I can't have another slow song on this record. I've got to speed this up. I came up with this chorus, crazy chorus. And then one time about a month later I just woke up and wrote the other five verses. Because I realized what it was, I knew what I had. And basically, all I had to do was speed up the slow verse with the chorus and then slow down the last verse so it was like the first verse, and then tell the story, which was a dream. It is from all these fantasies, all these memories that I made personal. Buddy Holly's death to me was a personal tragedy. As a child, a 15-year-old, I had no idea that nobody else felt that way much. I mean, I went to school and mentioned it and they said, 'So what?' So I carried this yearning and longing, if you will, this weird sadness that would overtake me when I would look at this album, The Buddy Holly Story, because that was my last Buddy record before he passed away."
This song made the 26-year-old McLean very famous very quickly, which was difficult for the songwriter. McLean was prone to depression, losing his father at age 15 and dealing with a bad marriage when recording the album. So when the song hit, it thrust him into the spotlight and took the focus away from the body of his work. In a 1973 interview with NME, he explained: "I was headed on a certain course, and the success I got with 'American Pie' really threw me off. It just shattered my lifestyle and made me quite neurotic and extremely petulant. I was really prickly for a long time. If the things you're doing aren't increasing your energy and awareness and clarity and enjoyment, then you feel as though you're moving blindly. That's what happened to me. I seemed to be in a place where nothing felt like anything, and nothing meant anything. Literally nothing mattered. It was very hard for me to wake up in the morning and decide why it was I wanted to get up."
Source: Songfacts.com (learn more at songfacts.com)