The name on Jennings's birth certificate was Wayland. It was changed after a Baptist preacher visited his parents and congratulated his mother for naming him after the Wayland Baptist University in Plainview, Texas. Lorene Jennings, who had been unaware of the college, changed the spelling to Waylon. Jennings later expressed in his autobiography, "I didn't like Waylon. It sounded corny and hillbilly, but it's been good to me, and I'm pretty well at peace with it right now."

When Jennings was eight, his mother taught him to play guitar with the tune "Thirty Pieces of Silver". Jennings used to practice with his relatives' instruments until his mother bought him a used Stella guitar.

"Once I mess with your mind,
Your little heart won't beat the same.
Lord, I'm a ramblin' man,
Don't mess around with any ol' ramblin' man.

After several disciplinary infractions 16-year-old Jennings was convinced to drop out of high school ... by the school superintendent. Upon leaving school, he worked for his father in the family store and formed a Country and Western/Bluegrass band--the Texas Longhorns.

On February 3, 1959, American rock and roll musicians Buddy Holly, Ritchie Valens, and J.P. "The Big Bopper" Richardson were killed in a plane crash near Clear Lake, Iowa. Jennings, a member of Holly's band at the time, was supposed to be on the plane but gave up his seat to Richardson who was suffering from the flu. The event later became known as "The Day the Music Died", after singer-songwriter Don McLean referred to it as such in his 1971 song "American Pie".

Jennings not only wrote and sang the theme song "Good Ol' Boys" but also provided narration for The Dukes of Hazzard and even played himself in one episode.

Wanted! The Outlaws, a compilation album by Waylon Jennings, Willie Nelson, Jessi Colter, and Tompall Glaser, earned its place in music history by becoming the first country album to be platinum-certified, reaching sales of one million.

During the final two hours of his six-hour shift which featured two hours of classic country, two hours of current country, and a couple hours of mixed recordings, Waylon pushed his luck too far. He liked to play Chuck Berry and Little Richard on the show. Each time he did, the station's owner would scold him. One night, Waylon played two in a row from Little Richard and was fired for it. Once an outlaw, always an outlaw.

In 1965, Jennings moved to Nashville, where he rented an apartment with country music's man in black, marking the start of a lifelong friendship.

"Take It to the Limit" was covered by Nelson and Jennings as the title track of their duet album, Take It to the Limit, which was released in 1983.