Waylon Jennings life saved.

Twist of fate gave Waylon Jennings life — and guilt

Waylon Jennings life saved.

“We’re put here on earth to make our own destiny. I don’t think there’s anything you can do this way or that way to change anything.”

Remembering Waylon “Hoss” Jennings, who died on February 13, 2002. He was 64.

In 1959, Waylon was a member of Buddy Holly’s band that was on a “Winter Dance Party” tour of the Midwest. Waylon and Buddy, both 22, were teen-age friends from Lubbock, Texas.

The weather in Minnesota that February night was rotten and Buddy decided to leave the tour bus and charter a small plane to get to the next venue in Moorhead, Minnesota.


The plane had room for only three passengers. It was decided that Buddy, Waylon and band member Tommy Allsup would take the plane, but band member The Big Bopper (J.P. Richardson) had the flu and wanted to get to Moorhead as soon as he could and asked Waylon for his seat on the plane.

When Buddy was told that Waylon was not going on the plane he said to his friend in jest, “Well, I hope your ol’ bus freezes up.” And Waylon replied in jest, “Well, I hope your ol’ plane crashes.”

About an hour and a half later, around 1 a.m., the plane crashed into a cornfield outside Mason City, Iowa, killing the three musicians and the pilot.

Crash site

The casual joke haunted Waylon for the rest of his life and led to years of a $1,500-a-day cocaine addiction.

”I did more drugs than anybody you ever saw in your life.”

He finally quit cold turkey in 1984.

In another twist of fate that wintry Minnesota night, 17-year-old band member Ritchie Valens asked Tommy Allsup for his seat on the plane. They tossed a coin to decide and Ritchie won the toss — and lost his life.

*[Backstory below]


Waylon lived another 42 years and recorded 60 albums, including sixteen country singles that topped the charts.

In the mid-1980s, he teamed up with Willie Nelson, Johnny Cash and Kris Kristofferson to form the quartet ‘The Highwaymen,’ making records and doing concert tours.

Waylon Jennings was inducted into the Country Music Hall of Fame in October 2001.


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4 thoughts on “Twist of fate gave Waylon Jennings life — and guilt

  1. I came across your old post about Waylon and just had to say a few words because he was the inspiration behind the naming of my old band "The County Outlaws." He was a hero and a legend in my eyes. He helped change the recording industry (for a time) by demanding that his band and not studio musicians backed him up on his albums. I got to see him Live in concert three times and loved every damn minute.

    He was one of the reasons I started a band in the first place and why I always had a preference for Outlaw Country music. And yes he almost died a few times with his drug addiction only to be saved and cleaned up by his later wife Jesse Colter. A true Legend with a hard living past as most legends before him endured. Waylon was and will always be right at the top of my list.

  2. Yeah, one of the best! He finally kicked his $1,500/day cocaine habit — cold turkey in 1984. Ah, yes, Jesse, “a good-hearted woman in love with a good-timing man.”

  3. I was lucky enough to be married to one for 30 years, until fate struck a fatal blow — I miss her every day.