Waylon Jennings & The Day the Music Died


Some of you might know this story, and some of you don’t. Some of you will find it interesting, some of you won’t. But I felt inclined to include it here because it involves one of our country heroes: Waylon Jennings.

Waylon got his break into the music scene by playing bass for Buddy Holly, who like Waylon, was from West Texas. Buddy’s band was called the Crickets, whose name was one of the inspirations for the name The Beatles. But Waylon was not a Cricket. The Crickets were kind of their own band who backed up Buddy Holly. But when the Crickets and Buddy were having some personal drama, Buddy decided to hire his friend Waylon and a guy named Tommy Allsup to come along with him on a tour that also included Ritchie Valens, and the Big Bopper.


(Waylon on the left)

It was a long tour through the upper Midwest in the dead of Winter, 1959. The tour started in Milwaukee, and would run for 25 straight days, ending in Springfield, IL. All the acts, crew, management, everybody rode in a tour bus to all the stops. They lived, slept, and ate in that bus. It was cramped, smelly, and the heater kept breaking so at night it might get down below 0. After a while the situation got to Buddy Holly, so for one of the legs he chartered a plane for him and his band to fly ahead so they could get some rest and clean up before the next show.

The plane was meant to be for Buddy, Waylon, and Tommy Allsup. But Ritchie Valens talked Tommy Allsup out of his seat, and Waylon gave up his seat the the elder Big Bopper.

“Ah,” Buddy Holly said to Waylon, “You’re not going with me tonight, huh? Did you chicken out?”

Waylon answered no, he wasn’t scared. The Big Bopper just wanted to go.

“Well,” Buddy said, grinning “I hope your damned bus freezes up.”

Waylon Jennings said “Well, I hope your ‘ol plane crashes.”

A lot of people know that Don McLean’s song ‘American Pie’ is about Buddy Holly’s plane crashing with Ritchie Valens and the Big Bopper, but a lot of people don’t know that Waylon was supposed to be on that plane, and only wasn’t because be was being a nice guy, showing respect to the elder performer.

At the time, Waylon Jennings and Buddy Holly were best friends. Buddy was going to cut Waylon into the music business. Buddy believed in Waylon as a performer and singer even more than Waylon believed in himself at the time. The promoters of the tour insisted the tour must go on, and Waylon wasn’t even able to attend the funeral.

After that, Waylon lost it. His best friend was dead, and so was his music career. His good time Rock ‘n Roll routine began to be mixed with the mournful soul of country music.

Nashville had no idea what it had in store.