Waylon Arnold Jennings (pronounced /ˈweɪlən ˈdʒɛnɪŋz/; June 15, 1937 – February 13, 2002) was an American singer, songwriter, musician, and actor. 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, Jennings gave up his seat on the ill-fated flight that crashed and killed Holly, J. P. Richardson, Ritchie Valens, and pilot Roger Peterson.
Jennings then worked as a DJ 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 Country 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." Jennings was featured in the 1978 album White Mansions performed by various artists documenting the lives of white people in the Confederacy during the Civil War. The songs on the album were written by Paul Kennerley. 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, which released three albums between 1985 and 1995. 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.
Jennings also appeared in films and television series. He was the balladeer for The Dukes of Hazzard, composing and singing the show's theme song. In 2001, he was inducted into the Country Music Hall of Fame, which he chose not to attend. In 2007, he was posthumously awarded the Cliffie Stone Pioneer Award by the Academy of Country Music.