Waylon Jennings epitomized the outlaw country music of the ‘70s. With his deep baritone voice and honky tonk sound, Jennings became a superstar almost two decades after he first emerged in the country music business. His "outlaw" sound, so spurred by his rejection of the Nashville pop-inflected tunes that were coming out of that Tennessee city, made way for other "outlaws" like Willie Nelson and Kris Kristofferson to follow in suit. Their independence and their ragged maverick style made them superstars as they influenced generations to come.

Jennings was born in Littlefield, TX where he played guitar and DJed for a local radio station. When he moved to Lubbock, TX in 1954 and started DJing for a radio station there, he befriended Buddy Holly, who became Jennings mentor. Their relationship would last a lifetime, as Holly helped create Jennings first single, and later Jennings joined Holly's band, the Crickets, as bassist. Jennings was actually supposed to sit on the plane that took Holly's life, but instead gave it up to a sick Big Bopper.

After the loss of his friend, he moved to Phoenix and created the rockabilly group the Waylors. The group had a little local success but not enough to make a big impact, so Jennings moved to Los Angeles in 1963 and earned a contract with A&M Records. While his music was pure country, it wasn't the pop country Herb Alpert wanted, so after a flopped single he moved on to RCA and Nashville. He released several hit singles that made the charts and created music that was both honky tonk and folk. When he renegotiated his contract to allow sole production he was finally able to showcase his sound. Throughout the ‘70s his albums hit the Top 50 and went gold. By the ‘80s, Jennings career was on the decline due to excessive drug use and loss of the outlaw movement. In 1985 Jennings, Johnny Cash, Willie Nelson and Kris Kristofferson formed the Highwaymen and released several albums over the next decade. He continued his success to the ‘90s, but his new work and live performances slowed down due to his health condition. He died in 2002.