Credited with helping found the Outlaw country sound, Waylon Jennings is a country music legend. He grew up learning to play guitar as a young boy, and began playing locally and eventually auditioned, as a teenager, for a radio program in his hometown of Littlefield, Texas.
Jennings ended up dropping out of high school and taking odd jobs to pay the bills while he continued performing on radio, and eventually DJ'ing his own show in Lubbock, Texas.
His distinctive baritone caught the ear of Buddy Holly, who produced Jennings' first single in 1958. Jennings also occasionally played in Holly's backing band The Crickets. He famously gave up his seat on the airplane that would eventually crash and kill both Holly and the band.
Holly's death shook Jennings, who paused his musical career and went back to DJ'ing. But eventually, in 1963, Jennings signed a contract with A&M Records. The label wanted him to perform more pop-leaning music. Jennings resisted and instead moved to Nashville and released three country albums in 1966: Folk-Country, Leavin' Town and Nashville Rebel.
Even though he wasn't being forced to play pop music, Jennings still chafed under Nashville's version of country. He continued releasing a series of commercial country albums while playing around with his sound. In 1973, Jennings released Honky-Tonk Heroes - an album credited with encapsulating the Outlaw sound he and Willie Nelson would come to make famous.
Based on the popularity of Outlaw country, Jennings teamed up with Nelson, Kris Kristofferson and Johnny Cash in the 1980s to form the supergroup the Highwaymen. The timing of the group followed Jennings' decision to get clean after a lengthy problem with drugs and alcohol.
They released three albums together over the course of a decade: Highwayman (1985), Highwayman 2 (1990) and The Road Goes On Forever (1995).
As Jennings got older, he was diagnosed with diabetes. Although it impacted his health, he continued performing music. He was inducted into the Country Hall of Fame in 2001.
Jennings died on February 13, 2002.