Waylon Arnold Jennings (born Wayland Arnold Jennings; June 15, 1937 – February 13, 2002) was an American singer, songwriter, and musician. He is best known as one of the founding pioneers of the Outlaw Movement in country music.

Jennings started to play guitar at age of eight and first performed at age 12 on KVOW radio, after which he formed his first band, The Texas Longhorns. Jennings left high school at age 16, determined to become a musician and worked as a performer and DJ on KVOW, KDAV, KYTI, KLLL, in Coolidge, Arizona, and Phoenix. In 1958, Buddy Holly arranged Jennings’s first recording session, and hired him to play bass. Jennings gave up his seat on the ill-fated flight in 1959 that crashed and killed Holly, J. P. “The Big Bopper” Richardson and Ritchie Valens.

Jennings then formed a rockabilly club band, The Waylors, which became the house band at “JD’s”, a club in Scottsdale, Arizona. He recorded for independent label Trend Records and A&M Records, but did not achieve success until moving to RCA Victor, taking on Neil Reshen as a manager, who negotiated significantly better touring and recording contracts for him. After he gained creative control from RCA Records, he released the critically acclaimed albums Lonesome, On’ry and Mean and Honky Tonk Heroes, followed by the hit albums Dreaming My Dreams and Are You Ready for the Country. During the 1970s, Jennings became one of the main figures of outlaw country. With Willie Nelson, Tompall Glaser and Jessi Colter he recorded country music’s first platinum album, Wanted! The Outlaws. It 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 people in the Confederacy during the Civil War. Jennings also appeared in films and television series, including Sesame Street, and a stint as the balladeer for The Dukes of Hazzard, composing and singing the show’s theme song and providing narration for the show. By the early 1980s, Jennings struggled with a cocaine addiction, which he overcame in 1984. Later, he joined the country supergroup The Highwaymen with Willie 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. In 2001, he was inducted into the Country Music Hall of Fame. In 2007, he was posthumously awarded the Cliffie Stone Pioneer Award by the Academy of Country Music.

Waylon Arnold Jennings was born on June 15, 1937, on the J.W. Bittner farm, near Littlefield, Texas. He was the son of Lorene Beatrice (née Shipley, 1920–2006) and William Albert Jennings (1915–1968). The Jennings family line descended from Irish and Black-Dutch. The Shipley line descended from Cherokee and Comanche families. 

https://www.youtube.com/watch?v=skh-Bv_vVC8