Waylon Jennings

Waylon Jennings embodied the outlaw country movement of the 1970s more than any other figure. Although he had worked as a professional musician since the final years of the 1950s, his imposing baritone and lean, modernized honky-tonk only propelled him to superstardom once the following decade arrived. He spurned Nashville conventions outright, bypassing the usual roster of studio musicians and ensuring his recordings never echoed the string-heavy, pop-tinged productions then flowing from the city. Fellow performers such as Willie Nelson and Kris Kristofferson embraced the same independent stance, allowing the broader “outlaw” movement—named for the artists’ unkempt, nonconformist image and their separation from Nashville—to become one of the decade’s most powerful country influences and to keep the genre anchored to its raw honky-tonk origins. Jennings himself wrote few songs, yet his sound, which merged the roughest elements of honky-tonk with rock & roll rhythm and attitude to produce music that was spare, direct, and sharp-edged, came to define hardcore country and later shaped countless musicians in the new traditionalist and alternative country movements of the 1980s.

Born and raised in Littlefield, Texas, Jennings mastered the guitar by age eight. At twelve he was already spinning records as a local radio DJ, and soon afterward he assembled his first band. He dropped out of school two years later, spent several seasons picking cotton, and finally relocated to Lubbock, Texas, in 1954. There he secured a post at station KLLL, where he met Buddy Holly at one of the station’s live shows. Holly took the young musician under his wing, sharing guitar techniques, co-writing material, and producing Jennings’ debut single, “Jole Blon,” issued by Brunswick in 1958. Later that year Jennings served as temporary bassist for Holly’s band the Crickets on the rock & roller’s last tour. He had also been booked on the fateful flight that claimed Holly’s life in early 1959, yet surrendered his seat at the final moment to the Big Bopper, who was battling a cold.

After Holly’s death Jennings returned to Lubbock, where he spent two years grieving his friend while working once more as a DJ. Late in 1960 he settled in Phoenix, Arizona, and formed the rockabilly outfit the Waylors. The group built a local following through steady appearances at the Phoenix club JD’s and signed with the independent Trend label in 1961. None of their singles gained traction, so Jennings took a job as a record producer at Audio Recorders. In 1963 he moved to Los Angeles and landed a contract with Herb Alpert’s A&M Records. By then his style had settled into pure country, yet Alpert pushed him toward the pop market; Jennings refused to compromise, and both his lone A&M single, “Sing the Girl a Song, Bill,” and the accompanying album failed to register.

With assistance from Chet Atkins and Bobby Bare, Jennings next obtained an RCA contract and relocated to Nashville in 1965. Upon arrival he shared a house with Johnny Cash, beginning a lifelong friendship that later produced their Highwaymen collaboration in the 1980s. His first RCA single, “That’s the Chance I’ll Have to Take,” appeared in summer 1965 and became a modest hit. The follow-up, “Stop the World (And Let Me Off),” reached the country Top 40 and initiated a run of moderate successes that soon yielded several Top Ten entries in 1968, among them “Walk on Out of My Mind,” “I Got You,” “Only Daddy That’ll Walk the Line,” and “Yours Love.” At this stage he still employed Nashville session players and cultivated a hybrid of honky-tonk and folk. As the new decade opened, however, he began steering his music toward hardcore country.

In 1970 Jennings cut several songs by the then-struggling Kris Kristofferson, which paved the way for the ambitious albums Singer of Sad Songs and Ladies Love Outlaws the following year. On those records he laid the groundwork for outlaw country by crafting a tougher, more muscular sound and selecting material from writers such as Alex Harvey and Hoyt Axton. During 1971 he also began working closely with Willie Nelson, jointly recording and composing several songs.

By 1972 Jennings had renegotiated his RCA deal to secure full production and creative control. The first album issued under the new terms, Honky Tonk Heroes, appeared in 1973. Built almost entirely from songs by the then-unknown Billy Joe Shaver and cut with Jennings’ road band, it delivered an edgy, bass-heavy, and defiant take on stripped-down honky-tonk. The fresh sound gradually attracted a wider audience, and in 1974 he scored his first number-one single with “This Time,” followed by another chart-topper, “I’m a Ramblin’ Man,” and the number-two hit “Rainy Day Woman.” Success continued through 1975: Dreaming My Dreams, which included his signature number-one single “Are You Sure Hank Done It This Way,” climbed to number 49 on the pop charts, and Jennings was named Country Music Association Male Vocalist of the Year.

He achieved mainstream crossover in 1976 when the various-artists collection Wanted! The Outlaws—centered on Jennings but also featuring his wife Jessi Colter, Willie Nelson, and Tompall Glaser—reached number one on the pop album chart. From that point forward Waylon became a bona fide superstar equally familiar to pop and country listeners. Over the next six years his albums routinely entered the pop Top 50 and earned gold certification. During this period he recorded several duets with Nelson, including the multi-platinum Waylon & Willie (1978), which contained the number-one single “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” Between the late 1970s and early 1980s he accumulated ten number-one hits, among them “Luckenbach, Texas (Back to the Basics of Love),” which peaked at number 25 pop and spent six weeks atop the country chart, plus “The Wurlitzer Prize (I Don’t Want to Get Over You),” “I’ve Always Been Crazy,” “Amanda,” “Theme from ‘The Dukes of Hazzard’ (Good Ol’ Boys),” and three additional duets with Nelson.

By the mid-1980s the pace of Jennings’ career slowed, owing both to his drug use and to the fading of the outlaw movement as a whole. He overcame his substance issues abruptly in the middle of the decade and joined Willie Nelson, Kris Kristofferson, and Johnny Cash in the supergroup the Highwaymen in 1985. The band issued three albums over the next ten years, though none surpassed the success of their debut, which featured the number-one single “Highwayman.” Also in 1985 Jennings left RCA for MCA Records. He enjoyed several early hits there, including the number-one “Rose in Paradise,” yet by the close of the 1980s he could no longer crack the country Top 40. In 1990 he moved to Epic Records, where “Wrong” reached the Top Ten and “The Eagle” entered the Top 40 the following year; after those modest showings, his singles stopped charting altogether.

Even as sales declined amid changing country tastes, Jennings remained a major attraction throughout the 1990s, consistently drawing large crowds and earning favorable reviews for many of his releases. He signed with Justice Records in 1996 and delivered the well-received Right for the Time. Closing In on the Fire followed in 1998. Health complications from diabetes later curtailed his activities, making walking difficult; his foot was amputated in December 2001, and he died at his Arizona home on February 13, 2002.