The Day The Music Died: Buddy Holly, Ritchie Valens, & The Big Bopper Tragically Die In A Plane Crash In 1959

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This day is famously known as “the day music died.”

On February 3rd, 1959, a Beechcraft Bonanza carrying rock and roll legend and pioneer, Buddy Holly, and several other artists, took flight from a small Iowa airport and flew into a blizzard, crashing about five miles from the airport and killing everyone on board.

Among the others killed were Ritchie Valens, J.P. “Big Bopper” Richardson, and the pilot, Roger Peterson. Buddy had chartered a plane that was supposed to take them to Moorhead, Minnesota, where they would be able to get a few more hours of sleep before the next run of shows on the Winter Dance Party tour.

Their tour bus heat had gone out days before, and one of the other band members actually had to leave in the middle of tour because they got frost bite on the bus… it was that cold on their Midwest run.

Being that they were zigzagging through the Midwest during a brutal winter, the band had already been stranded several times, and Buddy wanted to get where they were going and have time to catch up on laundry and things before the next show.

A Young Waylon Jennings

As the story goes, a young Waylon Jennings, who played bass guitar for Buddy at the time, was supposed to be on that plane, as well. But he offered his seat to a sick J.P. Richardson, and decided he would take the bus and meet up with the rest of the band at the next stop.

They’d actually been given a loaner bus after the engine of their regular bus froze up in Wisconsin a few days prior, so they were traveling in a converted school bus with no heat. Buddy jokingly told Waylon he hoped the bus would break down again since Waylon opted to drive on the freezing bus instead of fly, to which Waylon hauntingly responded:

“I hope your ol’ plane crashes.”

Buddy Holly was one of his very best friends, and the tragic event stuck with Waylon for the rest of his life, as did the lingering guilt that he narrowly evaded death when he didn’t understand why it all happened the way it did:

“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? It took a long time to figure that out, and it brought about some big changes in my life — the way I thought about things.”

Buddy was the first person to believe in Waylon’s musical talent, after they became friends when Waylon was a DJ at KLLL in Lubbock, Texas.

In 1958, Buddy financed, produced and played on Waylon’s first recording, “Jole Blon”.

In fact, two weeks before the aforementioned tour, Buddy bought Waylon a bass guitar and told him to learn how to play it before they hit the road. Waylon says he never took the time to learn to play the correct way, he just memorized every song in Buddy Holly’s catalog instead.

In his book, Waylon: An Autobiography, Waylon opened up about how he carried Buddy’s legacy into his own life and career, and how those lessons propelled him to the forefront of the outlaw country music movement of the 1970’s:

“He had a dose of Nashville where they wouldn’t let him sing it the way he heard it and wouldn’t let him play his own guitar parts. Can’t do this, can’t do that. ‘Don’t ever let people tell you you can’t do something,’ he’d say, ‘and never put limits on yourself.'”

Waylon clearly went on to become an iconic legend in his own right, but not without the unwavering belief in himself that Buddy helped him uncover years prior:

“Years later, I’d be in the studio, and the track would really get in the pocket and feel good, and I’d hear those Nashville producers saying scornfully, ’Man, that sounds like a pop hit.’

And I’d remember Buddy talking to me, telling me they thought he was crazy, as that freezing bus moved down the highway from Green Bay, Wisc., to Clear Lake, Iowa.”

Who knows if Waylon Jennings would’ve ever become the Waylon Jennings we all know and love now without the help of Buddy Holly, but it’s cool to look back and hear about just how much their friendship impacted Waylon’s career.

And really… it’s hard to imagine your mentor being someone more talented than Buddy Holly.

What’s more, is that Buddy did it because he truly believed in Waylon, wanted him to succeed, and was willing to do anything and everything he could to help him get there… even if Waylon didn’t always believe it or see it in himself. And it’s safe to say in retrospect, he was damn right about all of it.

Check out Waylon paying tribute to his friend in 1990 with a performance of “Peggy Sue”:

Of course, Don McLean dubbed February 3rd, 1959 as the “day the music died” in his 1971 hit “American Pie.” The album, of the same name, was dedicated to Buddy Holly, McLean’s musical idol.


And here’s that famous photo of Buddy and Waylon way back when, hanging out in New York City and playing around in a photo booth located in Grand Central Station while in town for tour rehearsals.

It’s one of my all-time favorites:

And here’s a rare recording of “Jole Blon” from 1958:

A beer bottle on a dock



A beer bottle on a dock