“The Day the Music Died”: How Waylon Jennings Nearly Ended Up in Don McLean’s “American Pie”

One of the most tragically iconic days in music history is “The Day the Music Died.” The title references the harrowing passing of Buddy Holly, Ritchie Valens, and J.P. Richardson, Jr. (The Big Bopper) in a plane accident that transpired on February 3, 1959. However, there was one more musician that very well could have ended up on the plane and suffered the same fate as the rest of the artists. That man is the one and only, Waylon Jennings.

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For a bit of context, Holly and his band, which consisted of Jennings, Tommy Allsup, and Carl Bunch were in the middle of Holly’s Winter Dance Party tour. Valens and Richardson were the supporting acts on the tour and traveled with them as well. Given the logistical nightmare the tour was, Holly decided to charter a plane to their next destination. Which was in Moorhead, Minnesota.

Taking off from Clear Lake Iowa, when all members of the tour were set to board the plane, Allsup and Jennings made some adjustments to their seating. Allsup lost his seat to Valens in a coin toss, whereas Jennings commendably gave his seat to Richardson given that he had the flu at the time. Well, Jennings’ generosity would ultimately turn into guilt thanks to the ending of the story.

Waylon Jennings’ Humorously Harrowing Quote

In retrospect, Jennings divulged a conversation he had with Holly right before the plane took off. When Holly learned Jennings wasn’t going on the plane, he stated, “Well, I hope your ol’ bus freezes up.” Jennings’ reply, “Well, I hope your ol’ plane crashes,” per the Texas Monthly.

Following the conversation, Jennings learned about the crash on the news and called his family to alert them that he had not boarded the plane. Despite the tragedy of the plane crash, the tour continued and Jennings became the lead singer of the band. Years later, Jennings would go to Nashville and sign his infamous deal with RCA Records in 1965.

Between Jennings’ decision and jest, one can’t even imagine what he was feeling the days, weeks, months, and years after the crash. However, fans, friends, and family members of Jennings would like to think that the two are somewhere else currently laughing about the dark joke and the result that tragically entailed. The day marked quite the blow for rock ‘n’ roll music as is, but imagine if the pioneer Outlaw country musician also boarded the plane on that fateful day…

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