Waylon Jennings' Eerie Last Words to Buddy Holly Before His Death: 'I Hope Your Ol' Plane Crashes' (2024)

Jack Irvin

·4 min read

Michael Ochs Archives/Getty; Beth Gwinn/Getty Buddy Holly, Waylon Jennings

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.

Waylon Jennings' Eerie Last Words to Buddy Holly Before His Death: 'I Hope Your Ol' Plane Crashes' (1)

Richard C. Miller/Donaldson Collection/Getty; Michael Ochs Archives/Getty Ritchie Valens, "The Big Bopper" J.P. Richardson

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.

RELATED: Celebrities Who Died in Plane and Helicopter Crashes

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.

Waylon Jennings' Eerie Last Words to Buddy Holly Before His Death: 'I Hope Your Ol' Plane Crashes' (2)

Michael Ochs Archives/Getty "The Day the Music Died"

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.'"

RELATED: Taylor Swift Sends Flowers to Don McLean After Beating 'American Pie' for Longest-Ever No. 1 Hit

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."

Waylon Jennings' Eerie Last Words to Buddy Holly Before His Death: 'I Hope Your Ol' Plane Crashes' (2024)

FAQs

What was Waylon Jennings last words? ›

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.

What were Buddy Holly's last words? ›

Jennings told the Country Music Hall of Fame that his last conversation with Holly would always haunt him, even though the words were in jest. After Jennings told Holly that he wouldn't be on the plane, Holly said, “I hope your dammed bus freezes up again.” Jennings replied, “I hope your ole plane crashes.”

Who didn't get on the plane when Buddy Holly died? ›

He booked a pilot for the trip who—it turned out—was under-trained for weather conditions. Holly and Valens were initially scheduled to take the plane along with a guitar player on the tour, Waylon Jennings. Not originally going to take the flight, The Big Bopper traded places with Jennings last minute.

Why did Buddy Holly's wife not attend his funeral? ›

On February 3, 1959, Buddy Holly died in a plane crash along with fellow musicians Ritchie Valens and The Big Bopper outside Clear Lake, Iowa. After learning of her husband's death from the television news, she suffered a miscarriage the following day and could not attend Holly's funeral in Lubbock.

Why couldn t Waylon Jennings walk? ›

He had been plagued with diabetes-related health problems in recent years that made it difficult for him to walk. In December, his left foot was amputated at a Phoenix hospital.

Did Buddy Holly's wife visit his grave? ›

"In loving memory of our own Buddy Holley," it says, using the original spelling of his surname. "September 7 1936 - February 3 1959". Maria Elena Holly, the musician's widow, has never seen the grave. Nor did she attend his funeral, which was held shortly after the 22-year-old's death in a plane crash 60 years ago.

What ever happened to Buddy Holly's wife and child? ›

Upon learning of his death, his wife Maria suffered a miscarriage and lost the child that she shared with Holly. His funeral was held four days later in Lubbock, Texas, attended by members of his family, and other musicians who were close to Buddy.

Who did Waylon give his seat to on the plane? ›

Ritchie Valens won one seat on a coin flip with Tommy Allsup, and Buddy assigned the other to his Panhandle pal. But soft-hearted Waylon gave his spot on the warm plane to Richardson, who had come down with the flu.

Did Waylon Jennings almost get on the plane with Buddy Holly? ›

The small plane carried only three passengers at a fee of $36 per person. Those three would be Buddy, Waylon Jennings and guitarist Tommy Allsup. However, fellow performer “The Big Bopper” had the flu and asked Waylon for his seat. Singer Richie Valens and Tommy Allsup flipped a coin for a seat.

Did Buddy Holly have any children? ›

Buddy Holly's $1 million fortune was mainly inherited by his widow as he had no children or other immediate family beneficiaries. Maria Elena made it her mission to preserve and promote the legacy of Buddy Holly, managing his music rights and establishing the Buddy Holly Educational Foundation.

Where was Buddy Holly going when his plane crashed? ›

Holly, the 22-year-old driving force of the tour, had enough of broken down busses in freezing temperatures and chartered a four-seater plane to get to the show the next night in Morehead, Minnesota, according to the Civil Aeronautics Board's Accident Report. Fargo, North Dakota, was the nearest airport.

What was Waylon Jennings buried at? ›

Noted Individuals. Noted individuals buried in the Mesa Cemetery include: Waylon Jennings - popular country/western singer and songwriter. Waylon Jennings grave is located on 9th Street.

Did Waylon Jennings have survivors guilt? ›

Waylon and Me and Survivor Guilt

Decades later Jennings said in an interview, “God almighty, for years I thought I caused it.” Wow. Waylon Jennings and I shared the same haunting guilty thought for so many years. Wouldn't we have had a whole lot to talk about if we'd had the chance!

Did Waylon Jennings have a funeral? ›

Country great Waylon Jennings was laid to rest Friday following a private graveside service in the Phoenix suburb of Mesa, Ariz.

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