Waylon Jennings frequented the #Palomino in its early years.  In one story, Tommy Thomas wanted Waylon to come back to the club after he became a successful artist.  Waylon demanded $20,000 in twenty dollar bills.  Tommy was happy to oblige and on the night of the act, Tommy provided the sum of $20,000 in a shoebox.  The rest is history.

Waylon Jennings was born on June 15, 1937, on the G.W. Bitner farm, near Littlefield, Texas. The Jennings family line descended from Irish and Black-Dutch. Meanwhile, the Shipley family moved from Tennessee and settled in Texas. The Shipley line descended from Cherokee and Comanche families.[1]

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 and providing narration for the show. 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.

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 as well as 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 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 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. On February 13, 2002, Jennings died from complications of diabetes.

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.

Waylon Arnold Jennings (pronounced /ˈweɪlən ˈdʒɛnɪŋz/; 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 gave up his seat on the ill-fated flight that crashed and killed Holly, J. P. Richardson, Ritchie Valens, and pilot Roger Peterson.

Curated from Waylon Jennings – Wikipedia