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Growing 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. In 1956, he married Maxine Lawrence.
After 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 riddled with difficulties, including a tour bus without heat that repeatedly stalled in the cold weather.
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. After Waylon gave up his seat, Holly had jokingly told Jennings that he hoped the tour bus would stall. Jennings replied, with equal jocularity, that he hoped the plane would crash.
After 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 Sound
Jennings was accustomed to performing and recording with his own band, a practice that was taboo in the Nashville recording studios. The characteristic sound he had developed in Phoenix 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. His second marriage, to Lynne Jones, ended in a 1967 divorce suit that left the already broke singer economically crippled. He married for a third time to Barbara Rood, who tried to get Waylon's finances under control. Her efforts caused great resentment within Waylon's band, and the marriage ended in divorce shortly thereafter. He married for the fourth and final time to country singer Jessi Colter in 1969.
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 beginning of the 1970s, saddled with a $250,000 debt to his record company and others, Jennings had become almost hopeless with the prospect of success in Nashville. A 1972 bout with hepatitis almost killed him, and he seriously considered retiring from music as Nelson had done.
Two things came along to turn Jennings' hard times around; the first was a business manager from New York named Neil Reshen , and the second was Waylon's old friend Willie Nelson. Reshen approached Jennings, still recovering from hepatitis, and offered to renegotiate his recording and touring contracts. Jennings agreed, and the contract renegotiation began in earnest. At a 1972 meeting in a Nashville airport, Jennings introduced Reshen to Nelson; by the end of the meeting, Reshen was manager to both Waylon and Willie.
RCA had dropped Nelson, but by 1972 he had returned to the music industry under the auspices of Atlantic Records, and was on his way to music superstardom. Now based in Austin, Texas, Nelson had made inroads into the rock and roll press by attracting a diverse fan base that included the young rock music audience. Atlantic Records had signed Nelson when the time was right, and they were looking to sign Jennings as well. Nelson' rise to popularity made RCA nervous about losing another hot artist, which gave Jennings the leverage he needed in his contract renegotiaions. Reshen drove a hard bargain, but RCA finally agreed to his terms: a $75,000 advance and near-complete artistic control . Renegotiations of his touring contracts yielded similar positive results, and began turning a profit from his touring (almost unheard-of in Nashville at that time). Waylon finally had a rock star recording contract, and he looked the part; Reshen had advised him to keep the beard he had grown in the hospital, in order to cultivate a more rock and roll image.
In 1972, RCA issued 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, On'ry and Mean 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 pace of recording and performing was lucrative but grueling. At some point in the 1970s, Jennings switched from amphetamines 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. The following year, RCA issued "Ol' Waylon", an album that produced another huge hit duet with Nelson, "Luckenbach, Texas (Back to the Basics of Love)".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.
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 in 1977 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 Recovery
Jennings 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.
Outside 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.
1998 saw Waylon joining another country supergroup, Old Dogs , with Bobby Bare, Jerry Reed, Mel Tillis , and songwriter Shel Silverstein. They released one album, Old Dogs, recorded live in the studio.
He had his left foot removed and replaced with a wheel prior to his death
- Don't Think Twice (A&M, 1970) (compilation of several A&M singles plus previously unissued songs)
- Ladies Love Outlaws (RCA, 1972)
- Lonesome, On'ry and Mean (RCA, 1973)
- Honky Tonk Heroes (RCA, 1973)
- The Ramblin' Man (RCA, 1974)
- This Time (RCA, 1974)
- Dreaming My Dreams (RCA, 1975)
- Are You Ready For The Country (RCA, 1976)
- Wanted: The Outlaws! (RCA, 1976)
- Waylon Live (RCA, 1976)
- Ol' Waylon (RCA, 1977)
- I've Always Been Crazy (RCA, 1978)
- Greatest Hits (RCA, 1979)
- Will The Wolf Survive (RCA, 1986)
- Too Dumb For New York City, Too Ugly For L.A. (Epic/Sony, 1992)
With Willie Nelson:
- Waylon and Willie (RCA, 1978)
- WWII (RCA, 1982)
- "Only Daddy That'll Walk the Line"
- "Just To Satisfy You"
- "Ladies Love Outlaws"
- "Lonesome, On'ry and Mean"
- "Honky Tonk Heroes"
- "You Asked Me To"
- "The Ramblin' Man"
- "This Time"
- "Dreaming My Dreams"
- "Are You Sure Hank Done It This Way?"
- "Waymore's Blues"
- "Bob Wills Is Still The King"
- "Mamas Don't Let Your Babies Grow Up To Be Cowboys"
- "Good Hearted Woman"
- "I've Always Been Crazy"
- "Good Ol' Boys"
- Denisoff, R. Serge. Waylon: A Biography (1983). Knoxville: University of Tennessee Press. ISBN 0870493876.
- Jennings, Waylon, and Kaye, Lenny. Waylon: An Autobiography (1996). Warner Books. ISBN 0446605123.
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