Waylon Jennings: West Texas, Guilt, and Outlaw Country

Waylon Arnold Jennings was born on June fifteenth, nineteen thirty-seven, in Littlefield, Texas, thirty-five miles northwest of Lubbock. By his early twenties he was working as a disc jockey at KLLL radio in Lubbock, and it was there that his life became permanently entangled with Buddy Holly's.

Holly heard Jennings on the air and recruited him to play bass on his nineteen fifty-nine winter tour. The two recorded together. In January of nineteen fifty-nine, Jennings and Holly were photographed together in a photo booth at Grand Central Terminal in New York.

Before the February second show at the Surf Ballroom in Clear Lake, Iowa, Holly chartered a small plane. He had secured seats for himself and two of his band members. When Holly learned that Jennings had given up his seat to the ailing Big Bopper, and that Tommy Allsup had lost his to Ritchie Valens on a coin toss, he and Jennings fell into banter. Jennings told Holly he hoped the plane crashed. He was joking. Holly told him he hoped the bus froze.

The plane went down. Jennings took the bus. For decades afterward he said publicly that the guilt from that exchange followed him through his life and contributed to years of substance abuse.

Jennings eventually returned to Texas and built a career as one of the founders of the outlaw country movement, rejecting Nashville's controlled production style in favor of raw, self-directed recording. Lubbock and the West Texas music tradition are part of the foundation that made that rebellion possible.