He was born in Littlefield, Texas.

Waylon Jennings was a country music performer for over forty years beginning in the 1950s when he worked with fellow Texan performers such as Buddy Holly. His collaborations with Willie Nelson include such classics as "Mamas Don't Let Your Babies Grow Up to be Cowboys". Jennings was also known as the voice of the narrator on the television series The Dukes of Hazzard.

On the fathful night of February 3, 1959 when the airplane with Buddy Holly, Ritchie Valens and J.P. Richardson (aka The Big Bopper) crashed outside of Mason City, Iowa killing the trio, It was suppose to be Jennings on the plane instead of Richardson. Since that incident Jennings has kept quiet about it until a few years before his death he admitted that he had strong feelings of guilt about whole thing and he felt that he should have died and not J.P. Richardson.

Jennings was married four times; the last and most successful marriage was to fellow country singer Jessi Colter.

Waylon Jennings died in Chandler, Arizona and is interred in the Mesa City Cemetery, Mesa, Arizona.