Jennings left school to pursue music professionally and he moved to Lubbock in the same pursuit in 1954. There he found work at a local radio station, KLLL, where he met and befriended early rock and roll star Buddy Holly.
He shifted to Arizona in 1961 and worked in radio for a while, before moving to Phoenix, where he formed a band, ‘The Waylors’. The band became famous locally and soon Jennings signed a contract with the independent label Trend Records.
Deals with Trend Records did not work out, which is why he moved to California in 1963 and signed with A&M Records. Even with his new record company, Jennings did not have much luck.
He was finally introduced to producer Chet Atkins by singer Bobby Bare, who signed him to RCA Victor in 1965. In the same year, his hit single ‘That’s the Chance I’ll Have to Take’ peaked the charts.
Jennings released his debut album ‘Folk-Country’ in 1966. It was followed by albums, ‘Leavin’ Town’ and ‘Nashville Rebel’ in the same year. ‘Nashville rebel’ was the soundtrack to an independent film of the same name, starring Jennings.
During the rest of the 1960s, Jennings released mid-chart albums, like, ‘Waylon Sings Ol’ Harlan (1967)’, ‘Love of the Common People (1967)’, ‘The One and Only (1967)’, ‘Hangin’ On (1968)’, ‘Jewels (1968)’, ‘Just to Satisfy You (1969)’, etc.
In 1972, he released ‘Ladies Love Outlaws’ and the hit single from the same album, with the same title became a huge hit. By this time Jennings got increasingly exasperated by his recording company’s creative hold on his music.
In the same year, he signed on Neil Reshen as his producer and he gained a new deal with RCA with complete artistic control. He released albums like: ‘Lonesome, On’ry and Mean (1873)’, ‘Honky Tonk Heroes (1973)’, ‘The Ramblin’ Man (1974)’, etc.
In 1976, Jennings released the album ‘Wanted! The Outlaws’, an album he recorded with Willie Nelson, Tompall Glaser, and Jessie Colter for RCA Records. The album was the first country music album certified platinum.
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The album ‘Waylon and Willie’ was released in 1978, and gave the hit single ‘Mammas Don't Let Your Babies Grow Up to Be Cowboys’. Another album ‘I've Always Been Crazy’ also released in the same year.
Jennings along with Johnny Cash, Kris Kristofferson and Nelson formed a band called ‘The Highwaymen’ in the mid-1980s. Apart from that he released: ‘Turn the Page (1985)’, ‘Sweet Mother Texas (1986)’, ‘A Man Called Hoss (1987)’, ‘Hangin’ Tough (1987)’, etc.
In the mid-1990s, he formed another group called ‘The Old Dogs’ with Bare, Jerry Reed and Mel Tillis; the group recorded a double album. After that, he formed ‘Waylon & The Waymore Blues Band’.
His last works were: ‘The Eagle (1990)’, ‘Too Dumb for New York City, Too Ugly for L.A. (1992)’, ‘Cowboys, Sisters, Rascals & Dirt (1993)’, ‘Waymore’s Blues (Part II) (1994)’, ‘Right for the Time (1996)’, ‘Closing In on the Fire (1998)’, etc.
Personal Life & Legacy
Jennings got married to Jessi Colter in 1969 and the couple remained married until his death. The couple had a son, Waylon Albright ‘Shooter’ Jennings.
He started consuming amphetamines at the time when he started living with Johnny Cash. He was arrested for conspiracy and possession of cocaine in 1977. But he was released due to lack of evidence.
His cocaine addiction escalated and it is said that he used to spend $1,500 every day to buy drugs. This left him in a huge debt and a subsequent bankruptcy. He came off cocaine completely in 1984.
He underwent heart bypass surgery in 1988 and in the following years he developed diabetes. He died in his sleep of diabetic complications in 2002 in Chandler, Arizona. He was buried in Mesa City Cemetery, Mesa, Arizona.