Born in the hardscrabble West Texas town of Littlefield on June 15, 1937, Waylon Jennings learned to play guitar and snagged a disc jockey job at a Littlefield station while still a boy. In 1958 he moved to Lubbock, where he worked as a DJ and met rising star Buddy Holly, with whom he toured and played electric bass during 1958 and 1959. It was Jennings who gave up his seat to the Big Bopper (J. P. Richardson) on the doomed 1959 plane flight that took the lives of Holly, Richardson, and singer Ritchie Valens.
The disaster stunned Jennings, and it took him several years to regain his momentum. But his time with Holly had been pivotal: "Mainly what I learned from Buddy," Jennings recalled, "was an attitude. He loved music, and he taught me that it shouldn't have any barriers to it." After working West Texas radio again, Jennings began performing at a bar called J. D.'s in Phoenix, Ariz. There he began to craft a sound that combined his aggressive Telecaster electric guitar style, his rough-edged vocals, and an eclectic repertoire that often borrowed from rockabilly, rock and folk.