How Buddy Holly Inspired Waylon Jennings to Be an ‘Outlaw’

by Clayton Edwards
(Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)

Buddy Holly was one of the most influential artists in early rock & roll music. Songs like “Peggy Sue” and “That’ll Be the Day” cemented Holly as a major part of American musical history. However, many may not know that he had a hand in inspiring one of the forefathers of Outlaw Country. Holly and Waylon Jennings were friends before Waylon’s career really took off. Before he passed away, Holly made a major impression on Jennings that would help shape the world of country music for decades to come.

Before we dig deeper into how Buddy Holly inspired Waylon Jennings to be an “Outlaw,” we should make sure we’re on the same page. To Waylon, being an Outlaw wasn’t some nefarious underground thing driven by criminal activity and drug abuse. Instead, it was about rebelling against Nashville’s musical establishment. In his autobiography, Waylon said, “For us, ‘outlaw’ meant standing up for your rights, your own way of doing things.”

How Buddy Holly Inspired Waylon Jennings’ Outlaw Spirit

In 1995, Waylon Jennings appeared on Ralph Emery on the Record to talk about his autobiography. During the interview, the two discussed Waylon’s friendship with Buddy Holly and the impact the late rocker had on the Outlaw icon.

Emery stated that Buddy Holly was one of the most influential people in Waylon’s life. Jennings agreed and went on to talk about how great of a guy Holly was. Then, he said, “I knew he liked me a lot and he was the first guy to really have a lot of confidence in me. Enough to prove it by doing something. He produced my first record.”

Waylon singing “Jole Blon” backed by Buddy Holly and King Curtis recorded in 1958

Emery pointed out that Buddy Holly wanted to make his music his way and asked if that was where Waylon got the philosophy. Waylon replied, “You know what? I never realized it until later, but it was.”

Waylon Jennings went on to explain that Decca Records brought Buddy Holly to Nashville and did “the very wrong thing” with him. They wouldn’t let Holly use his band to record. Instead, they forced him to use session players who weren’t used to his sound or style. This level of studio control, Waylon said, almost made Holly quit. Later, Holly went to Clovis, New Mexico to cut a demo of “That’ll Be the Day” and a few other songs with his band The Crickets. That’s what got the ball rolling for Holly.

“That’ll Be the Day”

Waylon Goes Outlaw

Waylon Jennings had his first recording session in 1958 in New Mexico. There, Buddy Holly produced the songs “Jole Blon” and “When Sin Stops” for Jennings. For more than a decade, Jennings would continue recording songs and albums that fit into the Nashville Sound. In the early seventies, he broke the mold by bringing his touring band into the studio. With 1973’s Honky Tonk Heroes, Waylon entered a new era of his career and helped to usher in the Outlaw Country movement. Without Buddy Holly showing him the way, he may have never made that change.