Texas PanhandleGrowing up in the abject poverty of the Dust Bowl, a young Waylon Jennings sought to escape the dirt roads of Littlefield. He began singing at an early age, winning a spot singing and playing guitar on a local radio show. He became a popular DJ for several Texas radio stations, and a musical performer on the early rock and roll performance circuit in Texas, alongside the likes of fellow Texans Roy Orbison and Buddy Holly.
Buddy HollyAfter Holly achieved national stardom, he offered to produce Waylon's first records. Though neither of the first two recordings had much success, it was the beginning of a short but influential friendship with the rockabilly legend. Holly asked Waylon to join his touring band playing bass guitar, an offer Waylon accepted despite the fact that he did not know how to play bass. They embarked on a nationwide tour.
On the night of February 3, 1959 (The Day the Music Died) the airplane carrying Buddy Holly, Ritchie Valens and J.P. Richardson (aka The Big Bopper) crashed outside of Mason City, Iowa, killing all passengers. Waylon had given his seat to Richardson, who had a cold and desperately needed rest. In his 1996 autobiography, Waylon admitted for the first time that in the years afterward, he felt severe feelings of guilt and responsibility for the crash.
PhoenixAfter several years of inactivity, Jennings began performing again, this time in Phoenix, Arizona. In these years of 2 and 3 shows a night, sometimes 6 nights a week, he developed a unique sound, a devoted following, and a decent living. He signed a contract with Herb Alpert's newly formed A&M Records, and he had a few hit singles on local radio in Phoenix, including "Four Strong Winds" (by Ian Tyson) and "Just To Satisfy You" (co-written with Don Bowman). Bobby Bare did his own cover of "Four Strong Winds" after hearing Waylon's version, and Bare later recommended Waylon to legendary country music guitarist and producer Chet Atkins, who signed Waylon to RCA Records. He packed up and moved to Nashville, Tennessee in 1965.
The Nashville SoundJennings was accustomed to performing with his own band, a practice that was taboo in the Nashville music establishment. His characteristic sound was further diminished by the typical post-production "sweetening" of recordings with string arrangements and other overdubs. Jennings released a series of singles and albums with RCA, but there were no runaway successes. He felt limited by the "Nashville Sound", the customary low payment, and the lack of artistic freedom in the 1960s country music industry. During this time, Jennings began using amphetamines while touring. He quickly became addicted, like many other country artists of the period, including his one-time roommate Johnny Cash.
Willie Nelson, another Texas native who had come to Nashville before him, retired from the music industry and left Nashville in the late 1960s. Nelson had cautioned Jennings not to leave his steady job as a popular performer in Phoenix for Nashville, but Jennings had not heeded his advice. By the end of the 1960s, thousands of dollars in debt to his record company and others, Jennings had become almost hopeless with the prospect of success in Nashville. A bout with hepatitis almost killed him, and he seriously considered retiring from music as Nelson had done.
Outlaw CountryTwo things came along to turn Jennings' hard times around. The first was a business manager and former lawyer named Neil Reshen. Reshen approached Jennings, still recovering from hepatitis, and offered to renegotiate his recording and touring contracts. At the urging of Jessi Colter and Richie Albright, Jennings agreed. In short order, Jennings gained artistic control over his recordings, better financial terms in his recording contract, and he began making money from touring (almost unheard-of in the country music industry at that time). Reshen also advised Jennings to keep the beard he had grown while in the hospital, to cultivate a more rock and roll image.
Around the same time, Willie Nelson had resurfaced, this time in Austin, Texas. Nelson had become popular in the Austin music scene, attracting a diverse fan base that included the young rock music audience. He emphatically invited Jennings to perform with him in Austin, which was gaining a reputation as the next "Music City, U.S.A." Jennings' successful incorporation of both stylistic and business aspects of rock music led to a rapid upsurge in his popularity.
In 1972, RCA released the album Ladies Love Outlaws, an album that Jennings never wanted released. Nevertheless, the title track is often considered the first song of the outlaw country movement. He followed this album with Lonesome, O'nry and Mean in 1972 and Honky Tonk Heroes in 1973, the first albums recorded and released under his own creative control. The albums were huge commercial and critical successes. More hit albums followed, with The Ramblin' Man and This Time in 1974 and Dreaming My Dreams in 1975. The 1970s saw his fourth and final marriage, this time to fellow country artist Jessi Colter. Also, by this time, Jennings had become heavily addicted to cocaine, consuming thousands of dollars worth every day.
In 1976, Jennings began his career-defining collaborations with Willie Nelson on the compilation album Wanted: The Outlaws!, country's first platinum record. Waylon and Willie followed in 1978, producing their biggest hit with "Mamas Don't Let Your Babies Grow Up To Be Cowboys". He released I've Always Been Crazy in 1978, followed with a greatest hits album in 1979 that produced another huge hit duet with Nelson, "Luckenbach, Texas (Back to the Basics of Love)".
By the early 1980s, Jennings was a hollow-eyed, wraithlike man tormented by addiction to cocaine. His personal finances had again unraveled, leaving him bankrupt. His work became less focused, and his tours had progressed into full rock and roll excesses. In a widely publicized case, he was arrested for cocaine possession by federal agents, though the charges were later dropped. The episode was recounted in Jennings' song "Don't Y'all Think This Outlaw Bit's Done Got Out Of Hand?"
Addiction and RecoveryJennings decided that it was finally time to clean up, at least for a little while. He underwent the detox process, intending to start using cocaine again in a more controlled fashion afterward. By Waylon's own admission in interviews, his son Shooter Jennings was the main inspiration to stay off of cocaine permanently. His later life was plagued with health problems likely related to his long cocaine addiction, including a heart attack and diabetes. Despite these problems, Jennings remained free from cocaine and continued recording and touring throughout the 1980s and 1990s.
Later YearsOutside of the music industry, Jennings was also known as the voice of the narrator on the popular television series The Dukes of Hazzard. The theme song "Good Ol' Boys", an original Jennings composition, is one of the most well known television theme songs in American television history.
In the mid-1980s, Johnny Cash, Kris Kristofferson, Nelson, and Jennings formed a successful group called The Highwaymen. Aside from his work with The Highwaymen, highlights from his own career include WWII with Willie Nelson in 1982, Will The Wolf Survive in 1985, and Too Dumb For New York City, Too Ugly For L.A. in 1992.
He released his autobiography, Waylon, in 1996.
Waylon Jennings died due to complications from diabetes in Chandler, Arizona and is interred in the Mesa City Cemetery, Mesa, Arizona.