Waylon Arnold Jennings was an American singer, songwriter, musician and actor. Jennings began playing guitar at 8 and began performing at 12 on KVOW radio. His first band was The Texas Longhorns. Jennings worked as a D.J. on KVOW, KDAV, KYTI, and KLLL. In 1958, Buddy Holly arranged Jennings's first recording session, of âJole Blonâ and âWhen Sin Stops .â Holly hired him to play bass. In Clear Lake, Iowa, Jennings gave up his seat on the ill-fated flight that killed Holly and others to J. P. Richardson, who was suffering from a cold. The day of the flight was later known as The Day the Music Died. Jennings then 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 and A&M Records, before succeeding with RCA Victor after achieving creative control.