Waylon Jennings — 5 Fascinating Facts About the Outlaw Legend
Born Wayland Jennings in Littlefield, Texas, in 1937, Waylon would grow up to become one of the defining forces of outlaw country. He lived hard, fought addiction, and reshaped Nashville on his own terms. Here are five fascinating facts about the man who refused to play by the rules.
1. He Started as a Teenage Radio DJ
As a boy, Waylon listened to the Grand Ole Opry with his father. By 14, he was already working in radio, eventually landing gigs at stations like KDAV and KLLL in Lubbock, Texas.
It was in Lubbock that he met a young rising star named Buddy Holly — a meeting that would change his life forever.
2. He Played Bass for Buddy Holly — and Gave Up His Seat on “The Day the Music Died”
Holly signed Waylon to his label and encouraged him to learn bass to join the Winter Dance Party Tour in 1959.
After a show at the Surf Ballroom in Clear Lake, Iowa, a small plane was chartered to the next stop. Waylon gave up his seat to J.P. “The Big Bopper” Richardson, who was ill.
In a chilling exchange, Holly joked that he hoped Waylon’s bus would freeze up. Waylon fired back, “Well, I hope your ol’ plane crashes.”
The plane went down, killing Holly, The Big Bopper, and Ritchie Valens. Waylon carried guilt over that final conversation for decades.
3. Chet Atkins Helped Launch His Career
After struggling for chart success in Arizona, Waylon caught the attention of Chet Atkins at RCA Records.
To Waylon, impressing Atkins was like impressing “God’s right hand” in country music. RCA signed him, beginning a long relationship that would eventually allow him to push back against Nashville’s polished production style.
4. He Roomed With Johnny Cash — and Helped Birth the Outlaw Movement
When Waylon moved to Nashville, he briefly lived with Johnny Cash. They bonded over music — and, at the time, pills.
Frustrated with creative restrictions, Waylon demanded artistic control. In 1973, he recorded Honky Tonk Heroes on his own terms. His first No. 1 hit, “This Time,” followed.
The outlaw era had officially begun.
5. He Helped Create the First Platinum Country Album
In 1976, Waylon joined forces with Willie Nelson, Tompall Glaser, and Jessi Colter for Wanted! The Outlaws.
It became the first country album to sell over one million copies.
Waylon and Willie went on to record iconic duets like:
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“Good Hearted Woman”
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“Mammas Don’t Let Your Babies Grow Up to Be Cowboys”
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“Luckenbach, Texas”
The Dark Side of the Outlaw
At the height of his fame, Waylon’s cocaine addiction spiraled into a reported $1,500-a-day habit. Legal trouble followed. So did near collapse.
Reflecting later, he admitted he kept chasing the first high — a feeling that never returned.
Eventually, with the support of Jessi Colter, Waylon got sober in 1984 and remained clean until his death in 2002.
Waylon Jennings was many things — survivor, rebel, romantic, cautionary tale.
But above all, he was exactly what he wanted to be:
An outlaw who did it his way.