Waylon Jennings has been played on NTS over 60 times, featured on 55 episodes and was first played on 17 January 2016.

Waylon Arnold Jennings (June 15, 1937 – February 13, 2002) was an American singer, songwriter, and musician. Jennings began playing guitar at eight and began performing at 14 on KVOW radio. His first band was The Texas Longhorns. Jennings worked as a DJ on KVOW, KDAV, KYTI, and KLLL. In 1958, Buddy Holly arranged Jennings's first recording session, of "Jole Blon" and "When Sin Stops (Love Begins)". Holly hired him to play bass. In Clear Lake, Iowa, the story is told that Jennings…