Waylon Arnold Jennings (pronounced; June 15, 1937 – February 13, 2002) 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 “Jole Blon” and “When Sin Stops (Love Begins).” 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.
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. That success 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. He toured less after 1997, to spend more time with his family. Between 1999 and 2001, his appearances were limited by health problems. On February 13, 2002, Jennings died from complications of diabetes.