Waylon Jennings' Eerie Last Words to Buddy Holly Before His Death: 'I Hope Your Ol' Plane Crashes'

In the 1971 classic "American Pie," Don McLean wrote about "The Day the Music Died" — a.k.a. Feb. 3, 1959, when Buddy Holly, Ritchie Valens and "The Big Bopper" J.P. Richardson were famously killed in a plane crash during a United States concert tour.

Five decades later, the tragedy was explored in a July 2022 episode of iHeartRadio's Too Much Information podcast, where hosts Jordan Runtagh and Alex Heigl break down McLean's hit song and discuss the events leading up to the plane crash.

Long before boarding the plane, Holly — famous for songs like "That'll Be the Day" and "Peggy Sue" — was performing shows throughout the Midwest on the Winter Dance Party tour alongside Valens, Richardson, Dion and the Belmonts as well as Frankie Sardo. The musicians referred to the shows as "the tour from hell," as they had to travel hundreds of miles each day and move all their own equipment in temperatures as low as -35 degrees Fahrenheit, per the podcast.

Weather conditions caused one performer to be hospitalized for frostbite, and many others came down with the flu. Holly was in a terrible mood in the hours leading up to a Feb. 2 concert in Clear Lake, Iowa — which would unknowingly be his last performance. After the show, he decided to avoid the cold and rent a private plane to fly himself and some of the musicians to their next gig in Fargo, North Dakota.

According to TMI, Holly planned to bring his band members, Jennings and Tommy Allsup, on the three-passenger plane. However, it's believed that Allsup was challenged to a coin toss by Valens, who ended up winning his seat on the ill-fated flight. Jennings also gave up his seat to Richardson, who'd gotten the flu and wanted to see a doctor before the next performance.

Supposedly, after hearing about the seat switch, Holly told Jennings, "Well, I hope your ol' bus freezes up." In an eerie response that allegedly haunted Jennings until his death in 2002, he replied, "Well, I hope your ol' plane crashes."

The flight took off at 12:55 a.m. on Feb. 3 and crashed into a cornfield about five minutes later, with the cause believed to be a weather-induced error on 21-year-old pilot Roger Peterson's part. He wasn't trained to fly in such poor conditions, which led to the crash that killed Holly at 22, Valens at 17 and Richardson at 28.

In the aftermath, Holly's wife Maria learned about his death on television and later suffered a miscarriage due to "psychological trauma," per the podcast. Similarly, his mother learned of his death while listening to the radio. The tragedy allegedly caused authorities to instate protocols requiring names of the deceased to be concealed from the public until family has been notified.

McLean, 77, wrote an essay for CNN about "American Pie" in 2009, noting that his appreciation for Holly's music partially inspired the song: "Buddy's death, for me, an impressionable 13-year-old, delivering papers, was an enormous tragedy. The cover photo of the posthumously released 'Buddy Holly Story' and 'The Buddy Holly Story, Vol. 2,' coupled with liner notes written by his widow, Maria, created a sense of grief that lived inside of me, until I was able to exorcize it with the opening verse of 'American Pie.'"

He wrote the song in 1970 inspired by America as a whole, with the plane crash contributing to its lyrics. "All of a sudden this memory of Buddy's death had the dramatic power that I needed and started my mind operating on a different level. And I was able to see where this song had to go, how big it had to be, how long it had to be," wrote McLean.

"Through my relationship with Buddy, I was able to discover my peculiar writing talent and, much to my amazement, help bring Buddy and his music back from the dead," continued the musician. "In a sense, 'American Pie' contains the spiritual connection to Buddy Holly that was always in me. It's as if we both gave each other new life."