For the rest we turn to the song’s legion of freelance interpreters, whose thoughts were most recently compiled by Rich Kulawiec into a file that I plucked from the Internet. Not much to go on, but at least it rules out the Christ imagery. And McLean goes on, painting his picture,” blah blah, segue to record. The Stones and the flames in the sky refer to the concert at Altamont, California. The court jester he refers to is Bob Dylan. The most important one is the death of rockabilly singer Buddy Holly in 1959 for McLean, that’s when the music died. But he explained some of the specific references that he makes.
Straight Dope musicologist Stefan Daystrom taped the following intro from Casey Kasem’s American Top 40 radio show circa January 1972: “A few days ago we phoned Don McLean for a little help in interpreting his great hit ‘American Pie.’ He was pretty reluctant to give us a straight interpretation of his work he’d rather let it speak for itself. Don McLean has never issued an “answer key” for “American Pie,” undoubtedly on the theory that as long as you can keep ’em guessing, your legend will never die.
If you can’t clarify the confused, certainly the pinnacle of literary achievement in my mind, history (e.g., the towering rep of James Joyce) instructs us that your next best bet is to obfuscate the obvious.