Jennings was a singer, songwriter, musician, and actor. He is
considered one of the pioneers of the outlaw movement in
country music.
Jennings started playing guitar at age eight and performed at
fourteen on KVOW radio,
In 1958, Buddy Holly arranged Jennings’s first recording session,
a cover of Jole Blon, and hired him to play bass. Jennings gave
up his seat on the ill-fated flight in 1959 that crashed and killed
Holly, J. P. "the Big Bopper" Richardson and Ritchie Valens.
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