Waylon Jennings

Who Was Waylon Jennings?

By the age of 12, Waylon Jennings was already immersed in the music scene, performing in a band and working as a radio DJ. Over the years, his musical style evolved, embracing a tougher, bass-driven sound that would become characteristic of outlaw country music. Jennings formed close friendships with influential artists, including Willie Nelson, and in 1985, he co-founded the legendary supergroup, the Highwaymen, alongside Nelson, Johnny Cash, and Kris Kristofferson. By the time of his passing, Jennings had firmly established himself as a country music superstar.

Early Career

Waylon Jennings was born on June 15, 1937, in Littlefield, Texas. He is best remembered for his pivotal role in popularizing outlaw country music, a genre known for its grittier and more rock-influenced sound. Alongside fellow artists, Jennings was labeled an “outlaw” for his rebellious stance against the traditional country music establishment and for his hard-partying lifestyle.

From a young age, Jennings demonstrated a passion for music, learning to play guitar as a child. By 12, he was already performing in bands and working as a disc jockey. In 1954, he dropped out of school and relocated to Lubbock, Texas, where he found employment at the local radio station KLLL. It was here that he met Buddy Holly, an early rock and roll star. In 1958, Holly produced Jennings’ first single, “Jole Blon,” and Jennings played in Holly’s backup band, The Crickets. On February 3, 1959, Jennings was slated to board a private plane with Holly after their performance at the Surf Ballroom in Clear Lake, Iowa. However, he selflessly gave up his seat to rock star J.P. Richardson, who was feeling unwell. Tragically, shortly after takeoff, the plane crashed, resulting in the deaths of Holly, Richardson, singer Ritchie Valens, and the pilot.

Devastated by the tragedy, Jennings returned to Lubbock, where he continued his work as a radio DJ. In 1960, he moved to Phoenix, Arizona, and revived his music career by forming a band called the Waylors. While the group cultivated a local following and recorded several singles through the independent label Trend, it never achieved commercial success. Nevertheless, Jennings secured a contract with A&M Records in 1963 and relocated to Los Angeles. Here, he encountered friction with the label over the artistic direction of his music, which they sought to steer toward a more pop-oriented sound. Remaining steadfast in his commitment to country music, Jennings released only one album under A&M.

Country Star

In 1965, Jennings made the pivotal move to Nashville, where he became roommates with Johnny Cash, a relationship that would blossom into a lifelong friendship. That same year, Jennings enjoyed his first country hit with “Stop the World (And Let Me Off).” By 1968, he had amassed a string of successful singles, including “Walk On Out of My Mind” and “Only Daddy That’ll Walk the Line.” His musical talent was recognized with a Grammy Award in 1969 for Best Country Performance by a Duo or Group with Vocal for “MacArthur Park,” a collaboration with the Kimberlys.

During this period, Jennings’ musical style continued to evolve, embracing a tougher, bass-driven sound. Collaborating with notable songwriters and artists like Kris Kristofferson and Willie Nelson, he released Honky Tonk Heroes in 1973, an album that is often regarded as a landmark in the development of the outlaw sound. This new style represented a significant departure from the polished productions of traditional country music, cultivating a devoted following. Jennings reached the pinnacle of the country charts in 1974 with “This Time,” marking his first number one hit, followed closely by another chart-topping success, “I’m a Ramblin’ Man.”

Crossover Success

Waylon Jennings achieved his first significant crossover success in 1975 when his single, “Are You Sure Hank Done It This Way,” reached the pop charts. Around this time, he was recognized by the Country Music Association as Male Vocalist of the Year, solidifying his status in the music industry. His involvement in the compilation album Wanted! The Outlaws (1976) further elevated his profile, as the album became a number one hit on the pop album charts. This landmark recording featured contributions from Jennings, Willie Nelson, Tompall Glaser, and Jessi Colter, who was also Jennings’ fourth wife. The couple collaborated on several duets, including a rendition of “Suspicious Minds.”

In 1978, Jennings partnered with Nelson to produce Waylon & Willie, which achieved multimillion-copy sales. One of the standout tracks, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” topped the charts and earned Jennings his second Grammy Award for Best Country Vocal Performance by a Duo or Group, shared with Nelson.

Throughout the late 1970s and into the early 1980s, Jennings continued to release hit songs, including “Luckenbach, Texas (Back to the Basics of Love)” and the iconic “Theme from The Dukes of Hazzard (Good Ol’ Boys).” In addition to performing the theme song for the popular television series, Jennings also served as its narrator.

Struggles

Despite his success, Jennings struggled with substance abuse, developing a costly cocaine and amphetamine habit that sometimes exceeded $1,500 per day. He made the decision to quit in 1984. The following year, he joined forces with Kris Kristofferson, Johnny Cash, and Nelson to form the Highwaymen, achieving a number one hit on the country charts with their song “Highwayman,” which was featured on their successful album of the same name. However, the follow-up album, Highwayman 2, released in 1990, did not achieve the same level of success.

While Jennings faced challenges in getting airplay on country music stations, he remained a beloved performer, touring extensively until 1997. He even participated in the 1996 Lollapalooza tour, which primarily showcased alternative rock acts. During this period, Jennings candidly documented his struggles and triumphs in Waylon: An Autobiography, co-authored with Lenny Kaye.

Diagnosed with diabetes in the early 1990s, Jennings experienced mobility issues in his later years. Nonetheless, he continued to create music, recording several performances at Nashville’s Ryman Auditorium for the album Never Say Die Live in 2000. In recognition of his contributions to music, he was inducted into the Country Music Hall of Fame in 2001. Later that same year, he faced a serious health setback when he had to undergo a foot amputation due to complications from diabetes.

Legacy and Death

Waylon Jennings passed away on February 13, 2002, at his home in Chandler, Arizona. He and Jessi Colter, married since 1969, had one child together, Waylon Albright “Shooter” Jennings. Additionally, Jennings had five other children from his previous marriages.

The news of his passing elicited profound sorrow from friends and fans. Kris Kristofferson remarked to the Los Angeles Times, “Waylon Jennings was an American archetype, the bad guy with the big heart.” Despite the challenges he faced in his later years, Jennings remained a figure filled with creativity and joy, as described by his son Shooter in an interview with People magazine.

Following in his father’s footsteps, Shooter Jennings has pursued a career in music, performing with various bands. He created an album featuring his father’s unreleased tracks, titled Waylon Forever, which was released in October 2008.