The Story of Waylon Jennings escaping fate on Buddy Holly’s doomed plane

At Bluescentric, it is the honor of a lifetime to dream up and manufacture official Waylon Jennings t-shirts merchandise on behalf of Waylon’s estate. As such, we get a lot of questions about the seat on that plane. So we give you the facts of that fateful moment in this article.

Buddy Holly, The Big Bopper and Ritchie Valens dying in a plane crash in Iowa was one of the most infamous & heartbreaking moments in rock n roll history.

It was one small twist of fate, just before that doomed flight, that set the path for future Outlaw Country music superstar Waylon Jennings to not only escape fate… but tempt it, by joking that he hoped the plane crashed.

And then it did.

Waylon Jennings was actually working as a radio DJ in Lubbock, Texas when a mutual friend recruited him to play bass for Buddy Holly’s upcoming tour. The only catch was that Waylon had never played bass, or toured, but he had two weeks to learn, so he did, and set out as part of Holly’s touring band.

By 1959, Buddy Holly was the up-and-coming everyman rock n roll hope that America gravitated to after Elvis left for the army. In just 18 months, Holly had established a string of hits like “That’ll Be the Day”, “Peggy Sue”, “Rave On”, “It’s So Easy”, etc. and he famously wrote and produced them himself.

So going out on tour with rock n roll’s next great star was a huge opportunity for Waylon.

Plus the tour included J.P. “The Big Bopper” Richardson, a DJ and singer who had a hit “Chantilly Lace”, and Ritchie Valens, who was currently enjoying the smash hit song “La Bamba”.

They were eleven dates into a 24-date tour run for the Winter Dance Party when they finished at the Surf Ballroom in Clear Lake, Iowa. The show date was actually an unscheduled stop; the promoters were just trying to fill an open date at the last minute.

After the show that night, they were supposed to head to Moorhead, Minnesota. The musicians were reportedly miserable on tour because the bus they were on was old, the heat was broken & the whole tour was in sub-freezing temperatures. It was so bad that Holly’s drummer got frostbite, and The Big Bopper was sick.

So the day before, Holly chartered a four-seat Beechcraft Bonanza for himself and two others to fly ahead to the next stop to do laundry & get some rest.

“Don’t ask me who I gave my seat to on that plane
I think you already know”
– Waylon Jennings, “A Long Time Ago”, 1978

There’s a longstanding rumor of a coin toss between Ritchie Valens and Waylon Jennings for who got the seat on the plane. The coin toss was actually between Tommy Alsup and Ritchie. Waylon willingly gave his seat up to The Big Bopper, who had the flu.

So before they parted ways for the next gig, Waylon and Buddy were sitting together waiting to leave when Buddy found out Waylon was driving not flying, and joked, “Well I hope your ol’ bus freezes up!”, with Waylon shooting back, “Well I hope your ol’ plane crashes!”

The plane took off in blinding snow in the dead of night from Mason City Municipal Airport at 12:55 AM CST, and within five minutes, the pilot failed to make the expected radio contact.

It wasn’t until sunrise the next morning that they found the wreckage of the plane in a cornfield just about five miles away. The plane had run into the ground at full speed, killing all four on board instantly.

The Clear Lake, Iowa police department said within minutes of the news breaking, they had people calling offering to buy Buddy’s glasses.

The deaths shocked the whole country. They called it “The Day The Music Died”. Holly’s pregnant wife miscarried. Songs were made about the tragedy. The two men who escaped fate had to deal with a lifetime of complicated feelings.

Waylon wrote in his autobiography that he had great survivor’s guilt over the ordeal. “I was so afraid for many years that somebody was going to find out I said that. Somehow I blamed myself. Compounding that was the guilty feeling that I was still alive.”

“I hadn’t contributed anything to the world at that time compared to Buddy. Why would he die and not me?”
– Waylon Jennings

Waylon wasn’t a success overnight. His ascent to the top took 15 years.

He moved to Phoenix, formed a band, and after years of playing in a local club signed with RCA Victor & moved to Nashville.

He had a few hits there, like “Only Daddy That’ll Walk the Line” at #2, but it wasn’t really until he’d gotten creative control and dropped the Outlaw Country 1973 classic Honky Tonk Heroes that Waylon’s ascended to country music legend.

Fifteen years after the plane crash, Waylon achieved his first #1 hit with “This Time”.

He’d achieve 15 more chart-toppers over the next decade.

Victims of The Day The Music Died:

Buddy Holly (22)
Ritchie Valens (17)
J.P. “The Big Bopper” Richardson (28)
Roger Peterson, Pilot (21)