Waylon Jennings

Holly hired him to play bass. During the "Winter Dance Party Tour," in Clear Lake, Iowa, Holly chartered a plane to arrive at the next venue. Jennings gave up his seat in the plane to J. P. Richardson, who was suffering from a cold. The flight that carried Holly, Richardson and Ritchie Valens crashed, on the day later known as The Day the Music Died. Following the accident, Jennings worked as a D.J. in Coolidge, Arizona and Phoenix. He formed a rockabilly club band, The Waylors. He recorded for independent label Trend Records, A&M Records before succeeding with RCA Victor after achieving creative control of his records.

During the 1970s, Jennings joined the Outlaw movement. He released critically acclaimed albums Lonesome, On'ry and Mean and Honky Tonk Heroes, followed by hit albums Dreaming My Dreams and Are You Ready for the Country. In 1976 he released the album Wanted! The Outlaws with Willie Nelson, Tompall Glaser and Jessi Colter, the first platinum country music album. The success of the album was followed by Ol' Waylon, and the hit song "Luckenbach, Texas (Back to the Basics of Love)". By the early 1980s, Jennings was struggling with a cocaine addiction, which he quit in 1984. Later he joined the country supergroup The Highwaymen with Nelson, Kris Kristofferson and Johnny Cash. During that period, Jennings released the successful album, Will the Wolf Survive. Read Less

The same year, at the peak of his success, Jennings began to feel limited by the outlaw movement. The "outlaw image" restricted the repertoire he could record, as well as the material that audiences expected from him. Jennings referred to the over-exploitation of the image in the song "Don't You Think This Outlaw Bit Has Done Got Out of Hand?", denouncing that the movement had become a "self-fulfilling prophecy". Read Less