Country music icon Waylon Jennings was born near Littlefield, Texas, on June 15, 1937, the son of William Albert and Lorene Bea (Shipley) Jennings. Waylon was born on the J. W. Bittner farm, where his father was working as a tenant farmer. The family later moved to Littlefield, where the elder Jennings ran a produce store.
Waylon learned to play the guitar before the age of ten and became a disc jockey on a local radio station by age twelve. He dropped out of high school and moved to Lubbock in 1954. There he met Buddy Holly on the KDAV radio program Sunday Party in 1955. Holly became a mentor to Jennings, coaching him in music and, in 1958, producing Jennings's first single, "Jole Blon." In 1959 Jennings joined Holly's band, the Crickets, just in time for the group's final tour. Two weeks later Holly died in the plane crash that also killed Ritchie Valens and J. P. (the Big Bopper) Richardson, to whom Jennings had given up his seat.
He spent two years mourning the loss of his friend and then moved to Phoenix, where he resumed his musical career. After forming a band called the Waylors and playing with great regional success, he moved to Nashville in 1965 and, partly as a result of his success with the Waylors, was soon signed to RCA by Chet Atkins. Jennings's first Top 10 hit came the following year.
His success was due to his baritone voice, his ability to perform in a way that convinced the listener of his sincerity, and his rebellious, even menacing, attitude; Jennings often dressed like a biker and, in fact, used members of the Hell's Angels as bodyguards. His music was different from that of the mainstream Nashville production studios, however. When they wanted to add studio musicians, string sections, and smooth background vocals to his recordings, he argued for the use of his touring band and a stripped-down sound. Jennings used his popularity as leverage against his recording label and was able to renegotiate his contract to allow him control over the production of his music.
Thereafter Jennings started to receive critical praise from outside the world of country music, and his influence and fame grew substantially. He turned his rebellious streak into performance by teaming up with Willie Nelson in the 1970s and forming the Outlaw movement of country music, a sub-genre that opposed what it saw as Nashville's mechanistic approach to making country music. Jennings's and Nelson's first Outlaw album, Wanted: The Outlaws (1976), was the first platinum album ever recorded in Nashville. It received the Country Music Association's awards for best album, best single, and best vocal duo of the year, though Jennings may not have been there to receive the awards; he often refused to attend music-award shows since he thought that artists should not compete with each other.
The Outlaw movement influenced a new generation of country music performers, encouraging the direction of New Traditionalists like Dwight Yoakam in the 1980s and subsequently the alternative-country movement of the 1990s. Jennings also continued to record solo albums during this time. His 1977 album Ol' Waylon was the first country album by a solo artist to go platinum. His 1979 Greatest Hits went quadruple platinum, which was an unprecedented mark of success in the country music industry of that time.
Jennings also gained notice through occasional film and television appearances. His only lead role in a movie was that of Arlin Grove in Nashville Rebel (1966), a largely autobiographical tale. He later appeared in the films Travelin' Light (1971), Moon Runner (1974), Follow That Bird (1985), and Maverick (1994), in addition to several made-for-TV movies. His most memorable work in television was his narration and singing the theme song for the hit show The Dukes of Hazzard. Jennings forged yet another new direction in country music in the 1980s by forming the superstar performing group the Highwaymen with Nelson, Johnny Cash, and Kris Kristofferson.
Beginning in the 1980s sales of Jennings' records slipped—the beginning of a continual decline in his commercial success. This was due to changing consumer tastes among country music fans in general, and also to his drug addiction. However, his popularity with his fans did not wane. His live shows continued to draw large crowds, and his recordings received critical praise throughout his life. In all, Jennings recorded more than sixty albums, earned thirteen gold records, and performed sixteen country songs that made it to the top of the Billboard charts. Although he did not write many songs himself, he is credited with creating a unique, gritty, edgy, and sparse sound that combined blues, rock-and-roll, and country. Jennings was inducted into the Texas Country Music Hall of Fame in 1999 and into the Country Music Hall of Fame in October 2001.
He had serious and well-publicized health problems. He developed a $1,500-a-day cocaine habit before he quit cold turkey in the early 1980s. Later he underwent heart surgery and was diagnosed as diabetic. Circulatory problems caused by his diabetes led to the amputation of his left foot in 2001. Jennings was married four times: to Maxine Carroll Lawrence (four children), Lynne Mitchell (one child), Barbara Rood, and his sometime musical partner Jessi Colter (one child). He died in Phoenix on February 13, 2002, and was buried in Mesa, Arizona. In 2007 Jennings was honored with a Lifetime Achievement Award at the Nashville Songwriter's Festival and the Cliffie Stone Pioneer Award from the Academy of Country Music. He was inducted into the Texas Heritage Songwriters’ Association Hall of Fame in 2014.