Cracked's 'One Hit Blunders': 5 Bizarre Background Details About 'American Pie'

Don McLean’s hit song "American Pie," the lead single off his second album of the same name, was released in 1971, spending four weeks at #1 on the Billboard charts. Clocking in at 8 minutes and 42 seconds long, the song held the record for longest song to top the charts for almost 50 years until Taylor Swift’s “All Too Well” (10 Minute Version) stole the crown.

But "American Pie" has become more than just a song, it’s a cultural landmark and a national treasure. It ranks #5 on The National Endowment for the Arts’ Songs of the Century list, and in 2017 it was added to the National Recording Registry by the Library of Congress. On the other hand, it also ranks at the top of many people’s lists of “So help me God, if that guy with the acoustic guitar starts playing that song, I’m gonna lose it” (tied with "Wonderwall").

So what’s the secret behind this song that has allowed it to endure in our culture for over half a century?

5 Writing And Recording

According to Don McLean, he wrote “American Pie” in two short sessions, coming up with the first part of the song and chorus in Cold Springs, New York, and finishing the rest in Philadelphia. Although he had been working out parts in his head over several months, McLean claims the actual pen-to-paper writing process only took about an hour total.

Each verse of the song ends with the line “the day the music died,” which famously references the 1959 plane crash that claimed the lives of Ritchie Valens, The Big Bopper, and McLean’s musical idol, Buddy Holly. The first verse of the song was largely autobiographical, as McLean first received word of the crash while he was delivering newspapers when he was 13 years old. The memory stuck with him, and he channeled it into the song.

While recording the song, McLean and his band were tracked live, meaning the entire band was recorded playing the song together at the same time instead of each element being taped separately and mixed together later. This gave the song a much more intimate vibe.

The single was actually released as American Pie (Parts I & II) because it was too long to fit on one side of a 45 vinyl record. They put half the song on side A and the other half on B. The song being a huge hit must’ve been great news for jukebox owners, as fans would have to pay twice as much just to hear the song in its entirety.

4 The Song Is Quite A Cash Cow

In all fairness, you can’t really call "American Pie" a one-hit-wonder. Don McLean has actually had many hit songs over his career, such as “Castles in the Air” and “Vincent,” as well as his covers of “Since I Don’t Have You” by the Skyliners and Roy Orbison’s “Crying.” Good songs that have earned him a ton of praise … but then again, none of those song titles get near equal billing next to McLean’s name on the concert posters, do they?

Don McLean earns around $500,000 a year in royalties from “American Pie” alone. And that’s just in a typical year with regular airplay. Those numbers get higher in years when huge stars like Madonna and Garth Brooks record covers of the song, or last year when it was included in films like Marvel’s Black Widow and Finch. Pretty good bank for a song he claims only took about an hour to write when he was 25 years old. Think about the most productive hour you had in your entire 20s, and imagine it netting you half a million a year for the rest of your life.

And that’s just the start. The original lyric sheets for the song sold for $1.2 million dollars back in 2015. McLean also holds the trademark on the words “American Pie,” which means Universal Pictures has had to fork over an undisclosed licensing fee any time they’ve put out an American Pie movie … Well, seven out of the nine or them anyway. Oh Lord, there are nine of those movies?!?

Oddly enough, "American Pie" may not even be McLean’s biggest money-maker. That would be "And I Love You So," which he wrote for his first album Tapestry in 1969 and has since been covered hundreds of times by artists like Perry Como, Johnny Mathis, Harry Connick, Jr., Rick Astley, etc. Elvis Presley recorded the song for his 1975 album Today and sang the song at every concert until his death.

3 Trying To Decipher the Song

With its near nine-minute length, "American Pie" is in the same category as songs like "Another Brick in the Wall" by Pink Floyd or Meatloaf’s “Paradise by the Dashboard Light” -- songs that are still in heavy rotation on classic rock stations but not necessarily because people requested them. Any time you hear songs like these on the radio, there’s a good chance the DJ needed a poop break. The length is one of the biggest complaints people have about the song. Is that a superficial reason for disliking it? Yes. Is that still a valid critique? Also yes. Really, no song on the radio needs to be longer than it takes to hard boil an egg.

When you compare "American Pie" to other hit songs, it’s kinda hard to really figure out how it works so well. It’s over twice as long as other singles, there’s nothing complex about the chord structure, no guitar solo, no bridge … it’s just verse, chorus, verse, chorus, etc., with only a couple of tempo changes to break it up. But once the song starts, it kinda holds you hostage whether you like it or not.

But one of the things that's helped sustain the song’s success over the years is the sheer density of the lyrics. McLean was cramming 12 years' worth of symbolism into a little under nine minutes, and his choice of words made the song a puzzle that people are still trying to figure out to this day, and Don McLean has largely kept his mouth shut over the meaning behind the song’s lyrics. “The day the music died” being about Buddy Holly was about all he was willing to admit for a while. As for what the rest of the lyrics were saying, McLean just said, "They're beyond analysis. They're poetry."

The fourth verse starting with the words “Helter Skelter,” was obviously a reference to the Beatles' song, and the rest of the verse is widely believed to be about their famous August 1965 concert at Shea Stadium. The metaphors get a little muddled, though. The entire verse is framed to be about a football game, and at the time of that concert, Shea Stadium was still set up for baseball, but whatever …

The fifth verse was pretty clearly about The Rolling Stone’s tragic Altamont Free Concert in 1969. There were references like “Jack Flash” (their song "Jumpin’ Jack Flash"), repeated mentions of Satan ("Sympathy for the Devil"), and “No angel born in Hell,” referring to the Hells Angels biker gang, who were hired to run security for the event and proceeded to let the whole event devolve into one huge bar fight. Perhaps the Hells Angels wanting $500 in beer as their fee should’ve been a red flag during the negotiation stage.

The third verse is where the speculation goes a little crazy though, particularly because of the line “When the jester sang for the king and queen.” The general consensus is that the jester was Bob Dylan, with the following lines, “In a coat, he borrowed from James Dean/And a voice that came from you and me,” calling out the coat Dylan wore on the album cover for The Freewheelin’ Bob Dylan and that he was often called “the voice of a generation.” Another reference to the jester being “on the sidelines in a cast” during the next verse’s football game could also be a reference to Dylan’s 1966 motorcycle accident that kept him away from touring and public appearances for eight years.

Dylan rebuffed the connection, saying, "A jester? Sure, the jester writes songs like ‘Masters of War,’ 'A Hard Rain's a-Gonna Fall,' 'It's Alright, Ma' – some jester. I have to think he's talking about somebody else."

The Identity of the king and queen in the song was the most heated debate. Fans’ theories have ranged from Pete Seeger and Joan Baez to JFK and Jackie Kennedy (with Lee Harvey Oswald now being the jester) to a little more on-the-nose interpretation of it meaning Dr. Martin Luther King, Jr. and Queen Elizabeth II, both of which Bob Dylan had previously performed for. Another theory was that the king was Elvis Presley, and the lines “Oh, and while the king was looking down/The jester stole his thorny crown” reference Dylan knocking Elvis off the top of the charts.

When the original lyric sheets went up for auction in 2015, the catalog of notes that came with them did contain mentions of Elvis and Bob Dylan, which did go to kinda confirm some of the theories. It didn’t reveal who the queen was, though. Ugh … at this point, any interviewer should be allowed to violently shake Don McLean if he starts to wax poetic about the details. It’s been over 50 years! Just tell us already, you old coot!

2 Why It Endures

"American Pie" is also a song chock full of contradictions. It’s a folk song about the spirit of rock ‘n roll. It’s a protest song about how everything was better before pop music had to make a statement. It’s a Dylanesque ballad that in part blames Bob Dylan for ruining everything.

The reason "American Pie" has remained so popular over the years is that the overall message of the song never becomes irrelevant. It’s a song about mourning the death of a bygone era and how great everything was in the good ol’ days before everything turned to garbage. It’s a metaphor for our culture continuing to lose its innocence to the point that we no longer recognize the world we once knew. Everyone can relate to that feeling. It could even be your entire worldview if you’re cynical enough.

Don McLean has stated in interviews many times how no one could get away with making a song like "American Pie" today. And you know what? He’s right! “American Pie” hit at just the right time. Don McLean captured lightning in a bottle. The lyrics came to him so easily because life wasn’t that great in 1971, and by looking back on all the turmoil of the '60s, it was pretty easy to think, “Man, I really miss the 1950s!”

There really hasn’t been any other period of time since then where that kind of serendipity could take place. Likewise, there hasn’t been a generation since then that has been able to have the same rose-colored nostalgia as the Baby Boomers. It’s not like any Gen-Xer in 2006 could get away with writing a song about how great things were before Kurt Cobain died and the boy bands took over.

1 Oh, And Don McLean Might Be A Monster

(TW: Abuse Claims)

As far as his music career is concerned, Don McLean has had a reputation for being more than a bit of a diva. Comedian and singer/songwriter Pat Godwin has an amazing story about his experience working with Don McLean on a gig back in the '80s, and it’s practically a masterclass in why you should never piss off your opening act. Nearly three decades on, Godwin still maintains his hatred of both Don McLean and “American Pie,” and after sharing his story, he’s found out he’s far from the only opener McLean has treated like garbage.

As for his personal life, buckle up because things are about to get dark. On January 18, 2016, Don McLean’s wife, Patrisha, called 911 on her husband for domestic assault. Don McLean was arrested without incident and later charged with six misdemeanor counts, to which he pleaded not guilty. Later, he pleaded guilty to four of those charges as part of a plea agreement which also allowed his charge of domestic violence assault to be dismissed after a year. This also allowed McLean to avoid any jail time and pay only a $3,000 fine. This event was the catalyst that led to the couple’s divorce after 29 years of marriage.

In the wake of the divorce, Patrisha McLean founded Finding Our Voices, an organization aimed at raising awareness for domestic assault victims in the state of Maine. Patrisha has not been shy about sharing all of her ex-husband’s lawyer’s attempts to keep Don McLean’s name from being mentioned in the group’s activities. At the opening of the group’s inaugural art exhibit, showed a typed letter she claims Don had forced her to sign stating that the fights they had were her fault, blaming her “premenstrual mental disturbances.” Yeesh.

In June of 2021, Don McLean’s daughter Jackie gave a tell-all interview with Rolling Stone about the alleged emotional and mental abuse she suffered at the hands of her father growing up. In the interview, she stated, “If somebody moved an item in the house and he didn’t know where it was, then he would go on a rampage for hours, and everyone was just constantly on edge because it was chaos.”

It did not take long after that interview for Don McLean to stop supporting his daughter financially and cut her out of his will. McLean told the Daily Mail that he was giving her upwards of $50,000 a year on top of the $3 million trust fund she stood to inherit upon his death, adding, “I'm just glad I'm not leaving my money to the people who are totally ungrateful and who don't like me. The truth has consequences. If my daughter and ex-wife feel this way then, good. Goodbye. I'm done.” And believe it or not, that’s even the harshest bitter divorce energy he gives off during the interview.

Don McLean made news again recently, and at least this time, it was because he actually managed to sense the tension in the room. MacLean had made the decision not to perform at the NRA national convention in Houston in May, just days after the deadly school shooting in Uvalde, Texas. McLean said in a statement that it would be “disrespectful and hurtful” for him to perform at the event in the wake of such a horrible tragedy. Lee “Proud to Be an American” Greenwood also bowed out of the concert, and man … when the NRA manages to lose two guys who have never passed up an opportunity to sing about America, you know it’s bad.

Dan Fritschie is a writer, comedian, and frequent over-thinker. He can be found on Twitter, and he thanks you for your time.

Top image: Don McLean, United Artists