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 Iora was one of the most infamous and heartbreaking moments in rock n roll history.

And one small twist of fate just before that fateful flight actually set the path for young future Outlaw Country music superstar Waylon Jennings to not only escaped fate, but tempt it by joking to Holly that he hoped his plane crashed. 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 learn he did, and they set out together on tour.

By 1959, Buddy Holly was the up-and-coming everyman great ray of rock n roll hope that America clinged to when Elvis left for the army. And 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.

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

So the day before, Holly chartered the four-seat Beechcraft Bonanza, so he and two others could 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 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 go when Buddy joked to Waylon, “Well I hope your ol’ bus freezes up!”, with Waylon joking 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 nearby cornfield. 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 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 said in his autobiography that he had great survivor’s guilt over the ordeal. He said, “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 some 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 saw Waylon’s ascent to country 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)