HomeEntertainmentMusicCountry Throwback: Watch Waylon Jennings Detail Moments Leading up to 1959 Buddy Holly Plane Crash

Country Throwback: Watch Waylon Jennings Detail Moments Leading up to 1959 Buddy Holly Plane Crash

by Emily Morgan
(Photo by Paul Natkin/Getty Images)

After tragically giving up his seat on the plane to Buddy Holly, Waylon Jennings would always be haunted by the last words he said before the fateful accident. 

Holly hired Jennings as a bassist for his new band after Holly decided to disband from The Crickets. In 1959, Jennings and Holly took off on The Winter Dance Party Tour beginning on January 23 in Milwaukee, Wisconsin, and then continued across the midwestern U.S. 

Due to a lack of planning, the distance between tour dates hadn’t been accounted for, causing a headache for all the band members. 

Soon after the tour kicked off, the bus no longer had a heater due to a mechanical breakdown, and the band began to get sick as a result: the drummer, Carl Bunch, was even hospitalized with frostbitten toes.

On February 2, the tour made an unscheduled stop in Clear Lake, IA. Although they weren’t planning on playing that night, tour presenters offered a show to a local venue owner; thus the band was slated to play. 

The Last Moments Between Waylon Jennings & Buddy Holly

Following the show, Holly decided to charter a plane to Fargo, North Dakota, where the rest of the band would meet him. After midnight, Holly, Jennings, and Tommy Allsup were getting ready to take off. However, another musician on tour J.P. Richardson (“The Big Bopper”) asked Jennings for his seat since he came down with the flu and needed rest. Little did they know, a coin toss would change history forever.

When Holly learned that Waylon Jennings was giving his seat up, he jokingly teased the soon-to-be country star. “I hope your ass freezes on the bus!”

In a similarly playful manner, Waylon Jennings fired back what would late become the words he’d always regret. 

“Here I am, about 19-years-old and I said, ‘Yeah, well I hope your old plane crashes,’ and God almighty – for years I thought I had caused it…” Jennings recalled. 

Just minutes after takeoff, the plane carrying the three musicians, Buddy Holly, J.P. Richardson, and Ritchie Valens, crashed into a cornfield after a storm paired with an inexperienced pilot took down the plane. 

Nearly two decades after the accident, Waylon Jennings wrote a song dedicated to his lost friend and the emotional regret he felt after Holly’s death.

The song Old Friend was released on Waylon Jennings’ album, Are You Ready For The Country, in June 1976. It was soon certified gold, topping the “Billboard Country Albums” chart.