Waylon Arnold Jennings (June 15, 1937 – February 13, 2002) was a pioneering American country music singer, songwriter, musician, and actor, known for his role in popularizing the outlaw country genre. Born in Littlefield, Texas, Jennings began playing guitar at age eight and by twelve was performing in a band and working as a radio DJ. He left high school at sixteen to pursue music full-time and eventually met Buddy Holly, who produced Jennings' first single "Jole Blon" and included him in his band, The Crickets. Jennings narrowly avoided the 1959 plane crash that killed Holly, J.P. "The Big Bopper" Richardson, and Ritchie Valens by giving up his seat.

After a period of working as a DJ in Lubbock, Texas, Jennings moved to Phoenix, Arizona, where he formed the band the Waylors. Despite initial struggles, he signed with RCA Victor in 1965 and moved to Nashville, where he became roommates with Johnny Cash. Jennings' music evolved into a tougher, more rock-influenced style, leading to his association with the outlaw country movement alongside Willie Nelson. His critically acclaimed albums "Lonesome, On'ry and Mean" and "Honky Tonk Heroes" marked the beginning of his success, followed by the first platinum country album "Wanted! The Outlaws" with Nelson, Tompall Glaser, and Jessi Colter.

Jennings achieved crossover success with hits like "Luckenbach, Texas" and "I'm a Ramblin' Man," and he contributed to the theme song of "The Dukes of Hazzard." He overcame cocaine addiction in 1984 and later joined the supergroup the Highwaymen with Nelson, Cash, and Kris Kristofferson. Jennings' legacy includes 16 number one hits, 11 number one albums, and induction into the Country Music Hall of Fame in 2001. He passed away in Chandler, Arizona, in 2002, leaving a lasting influence on country music.