Waylon Jennings was born on June 15, 1937, in Littlefield, Texas. By age 12 he was playing in a band and working as a radio DJ. His style evolved over time, taking on a tougher, more bass-driven sound. He befriended such artists as Willie Nelson, and formed the Highwaymen with Nelson, Johnny Cash, and Kris Kristofferson in 1985. By the time of his death, Jennings had become a country music superstar.
A musical rebel, Waylon Jennings was born on June 15, 1937, in Littlefield, Texas, and is best remembered for helping to popularize a grittier and more rock-influenced style of music known as outlaw country music. He and some of his fellow artists were labeled "outlaws" for challenging the country music establishment and for their hard-partying ways.
Jennings learned to play guitar as a child. By the age of 12, he was playing in a band and working as a radio disc jockey. Jennings dropped out of school and moved to Lubbock in 1954. There he found work at a local radio station, KLLL, where he met and befriended early rock and roll star Buddy Holly. In 1958, Holly produced Jennings' first single, "Jole Blon," and Jennings played in Holly's backup band, The Crickets, for a time. He was performing with the group on February 3, 1959, and he was supposed to get on a private plane with Holly after their show at the Surf Ballroom in Clear Lake, Iowa. Jennings, however, gave up his spot on the plane to rock star J.P. Richardson—better known as "The Big Bopper"—who wasn't feeling well. Shortly after takeoff, the plane crashed, killing Holly, Richardson, singer Ritchie Valens, and the pilot.
Heartbroken after the tragedy, Jennings returned to Lubbock for a time and worked as a radio disc jockey. He moved to Phoenix, Arizona, in 1960 and restarted his musical career, forming a band called the Waylors. The group developed a local following and even recorded some singles through the independent record label Trend.
While the band never really took off commercially, Jennings landed a contract with A&M Records in 1963 and moved to Los Angeles, California. He got into a conflict with the record label over the direction of his music. They wanted him to take on more of a pop sound. Not one to be pushed around, Jennings remained committed to his country style. He made only one album for A&M.
In 1965, Jennings moved to Nashville. He became roommates with country music's man in black, Johnny Cash, which marked the start of a lifelong friendship. That year Jennings had his first country hit, "Stop the World (And Let Me Off)." By 1968, he had several successful singles, including "Walk On Out of My Mind" and "Only Daddy That'll Walk the Line." Jennings won his first Grammy Award in 1969 for Best Country Performance by a Duo or Group with Vocal for "MacArthur Park," which he recorded with the Kimberlys.
Around this time, Jennings' musical style continued to evolve, taking on a tougher, more bass-driven sound. He worked on songs with such songwriters and artists as Kris Kristofferson and Willie Nelson. In 1973, Jennings released Honky Tonk Heroes, which is often seen as one of the early albums displaying his new so-called outlaw sound. This new style was a distinct break from the slick productions of the more traditional country music and began to develop its own following. Reaching the top of the country charts in 1974, "This Time" was the first number one hit for Jennings and was quickly followed by another chart-topper "I'm a Ramblin' Man."
Jennings got his first taste of crossover success in 1975 when "Are You Sure Hank Done It This Way" made its way onto the pop charts. Around that same time, he was honored by the Country Music Association as Male Vocalist of the Year. Jennings' participation in the compilation Wanted! The Outlaws (1976) helped him become an even bigger name in music. A number one hit on the pop album charts, the recording featured songs by Jennings, Willie Nelson, Tompall Glaser, and Jessi Colter, Jennings' fourth wife. The couple even sang several duets together, including a cover of "Suspicious Minds."
Joining forces with Nelson, he recorded Waylon & Willie (1978), which went on to sell several million copies. One of their duets from the album, "Mammas Don't Let Your Babies Grow Up to Be Cowboys," reached the top of the charts and gave Jennings his second Grammy Award. He and Nelson shared the honors for Best Country Vocal Performance by a Duo or Group.
For the rest of the decade and into the early 1980s, Jennings continued to make hits, including "Luckenbach, Texas (Back to the Basics of Love)" and "Theme from 'The Dukes of Hazzard' (Good Ol' Boys)." In addition to creating the theme song for the television series, Jennings served as the narrator for the country comedy The Dukes of Hazzard.
Long known for his partying ways, Jennings' drug use escalated into an expensive cocaine and amphetamine habit, which sometimes cost him as much as $1,500 a day. He decided to quit in 1984. The following year, Jennings teamed up with Kris Kristofferson, Johnny Cash, and Willie Nelson to form the Highwaymen. They hit the top of the country charts with "Highwayman," which was included on their successful album of the same name. The 1990 follow-up album, Highwayman 2, did not fare as well.
While he had a tough time getting his music played on country music stations, Jennings remained a popular performer, touring extensively until 1997. He even played a few dates on 1996 Lollapalooza tour, better known for showcasing alternative rock acts. Around this time, Jennings candidly shared his many ups and downs in Waylon: An Autobiography, written with Lenny Kaye.
Diagnosed with diabetes in the early 1990s, Jennings had trouble walking in his later years. But that did not stop him from making music. In 2000, Jennings recorded several performances at Nashville's Ryman Auditorium for the album Never Say Die Live. He was inducted into the Country Music Hall of Fame in 2001. Later that year, Jennings had to have a foot amputated due to diabetes-related poor health.
Jennings died on February 13, 2002, at his home in Chandler, Arizona. Married since 1969, he and Jessi Colter had one child together, Waylon Albright "Shooter" Jennings. Jennings had five other children from his three previous marriages.
Friends and fans alike mourned the passing of the country music superstar. "Waylon Jennings was an American archetype, the bad guy with the big heart," Kristofferson told the Los Angeles Times. Despite his difficult final years, "he was filled with creativity and joy," his son Shooter explained to People magazine.
Shooter Jennings has followed his father's footsteps, playing in a number of bands. With his backup band, the .357s, he put together an album of his father's music consisting of tracks recorded years before Waylon's death. The recording, Waylon Forever, was released in October 2008.
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