Waylon Arnold Jennings (born Wayland Arnold Jennings, June 15, 1937 – February 13, 2002) was an American country music singer, songwriter, musician, and actor. He is considered one of the pioneers of the outlaw movement in country music.
Jennings started playing guitar at age eight and performed at 14 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, a cover of "Jole Blon", and hired him to play bass. Jennings gave up his seat on the ill-fated airplane flight in 1959 that crashed and killed Holly, J. P. "the Big Bopper" Richardson and Ritchie Valens.
Jennings then returned to Texas, taking several years off from music before eventually moving to Arizona and forming a rockabilly club band, the Waylors, which became the house band at JD's, a club in Tempe, Arizona. He recorded for independent label Trend Records and A&M Records, but did not achieve success until moving to RCA Victor in 1965. In 1972 he hired Neil Reshen as his manager, who negotiated significantly better touring and recording contracts. After Jennings 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 featuring number-one hit "Are You Sure Hank Done It This Way" and Are You Ready for the Country.
During the 1970s, Jennings drove 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 another platinum album, a first for any solo artist in country music, Ol' Waylon, and the hit song "Luckenbach, Texas". He was featured on the 1978 album White Mansions, performed by various artists documenting the lives of Confederate Southerners during the Civil War. He appeared in films and television series, including Sesame Street and a stint as the Balladeer on The Dukes of Hazzard, composing and singing its theme song and narrating the show.
Jennings struggled with 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 has been named as one of the innovators of progressive country.
Jennings toured less after 1997 to spend more time with his family. Between 1999 and 2001, health problems limited his appearances. 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 presented by Weylon Hofacket.
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, 1919–2006) and William Albert Jennings (1911–1968). The Jennings family line descended from Irish and Black-Dutch. He was the oldest of four sons, followed by Tommy Jennings (1941–2019), James Jennings, and Bo Jennings (1950–2018). The Shipley line descended from his great-grandfather, a farmer and lawman from Tennessee, with Jennings adding that "along the way, a lot of Indian blood mixed in," including Cherokee and Comanche families.
The name on Jennings's birth certificate was Wayland. It was changed after a Baptist preacher visited his parents and congratulated his mother for naming him after the Wayland Baptist College, in Plainview, Texas. Lorene Jennings, who was Church of Christ and had been unaware of the college, changed the spelling to Waylon. Jennings later expressed in his autobiography, "I didn't like Waylon. It sounded so corny and hillbilly, but it's been good to me, and I'm pretty well at peace with it now." After working as a laborer on the Bittner farm, Jennings's father moved the family to Littlefield and established a retail creamery.
When Jennings was 8, his mother taught him to play guitar with the tune "Thirty Pieces of Silver". Jennings used to practice with his relatives' instruments until his mother bought him a used Stella guitar, and later ordered a Harmony Patrician. Early influences included Bob Wills, Floyd Tillman, Ernest Tubb, Hank Williams, Carl Smith, Dean Martin, and Elvis Presley.
Beginning with performing at family gatherings, Jennings played his first public concert at the Youth Center with Anthony Bonanno, followed by appearances at the local Jaycees and Lions Clubs. He won a talent show at Channel 13, in Lubbock, singing "Hey Joe". He later made frequent performances at the Palace Theater in Littlefield, during local talent night.
At age 14, Jennings auditioned for a spot on KVOW in Littlefield, Texas. Owner J. B. McShan, along with Emil Macha, recorded Jennings's performance. McShan liked his style and hired him for a weekly 30-minute program. Following his performance on the show, Jennings formed his own band. He asked Macha to play bass for him and gathered other friends and acquaintances to form the Texas Longhorns. The style of the band—a mixture of country and western and bluegrass music—was often not well received.
After several disciplinary infractions, 16-year-old Jennings was convinced to drop out of Littlefield High School by the superintendent. Upon leaving school, he worked for his father in the family store and also took temporary jobs. Jennings felt that music would turn into his career. The next year he, along with the Texas Longhorns, recorded demo versions of the songs "Stranger in My Home" and "There'll Be a New Day" at KFYO radio in Lubbock. Meanwhile, he drove a truck for the Thomas Land Lumber Company, and a cement truck for the Roberts Lumber Company. Tired of the owner, Jennings quit after a minor driving accident. Jennings, and other local musicians, often performed at country radio station KDAV. During this time he met Buddy Holly at a Lubbock restaurant. The two often met during local shows, and Jennings began to attend Holly's performances on KDAV's Sunday Party.
In addition to performing on air for KVOW, Jennings started to work as a DJ in 1956 and moved to Lubbock. His program ran from 4:00 in the afternoon to 10:00 in the evening, filled with two hours of country classics, two of current country, and two of mixed recordings. The latter included early rock-and-roll stars such as Chuck Berry and Little Richard. The owner reprimanded Jennings for his selection, and after playing two Little Richard records in a row Jennings was fired.
During his time at KVOW Jennings was visited by DJ Sky Corbin of KLVT in Levelland. Corbin was impressed with his voice, and decided to visit Jennings at the station after hearing him sing a jingle to the tune of Hank Snow's "I'm Moving On". Jennings expressed his struggle to live on a $50-a-week salary. Corbin invited Jennings to visit KLVT, where he eventually took Corbin's position when it opened. The Corbin family later purchased KLLL, in Lubbock. They changed the format of the station to country, becoming the main competition of KDAV. The Corbins hired Jennings as the station's first DJ.
Jennings produced commercials and created jingles with the rest of the DJs. As their popularity increased, the DJs made public appearances, and Jennings's events included live performances. During one performance, Holly's father, L. O. Holley, approached them with his son's latest record and asked them to play it at the station. Holley mentioned his son's intention to start producing artists himself, and Corbin recommended Jennings. After returning from his tour of England, Buddy Holly visited KLLL.
Holly took Jennings as his first artist. He outfitted him with new clothes, and worked with him to improve his image. He arranged a session for Jennings at Norman Petty's recording studios in Clovis, New Mexico. On September 10, Jennings recorded the songs "Jole Blon" and "When Sin Stops (Love Begins)" with Holly and Tommy Allsup on guitars and saxophonist King Curtis. Holly then hired Jennings to play bass for him during his "Winter Dance Party Tour".