Who Was Waylon Jennings?

by James HargroveJune 21, 2022
Who Was Waylon Jennings?

Waylon Jennings began playing in a band and working as a radio DJ at the age of 12. His style changed over time, becoming more aggressive and bass-driven. He befriended performers like Willie Nelson, and together with Nelson, Johnny Cash, and Kris Kristofferson, he created the Highwaymen in 1985. By the time of his passing, Jennings was a country music icon.

Early Career

Waylon Jennings was born in Littlefield, Texas, on June 15, 1937, and is most known for helping to promote outlaw country music, which is grittier and more rock-influenced. They were called “outlaws” for questioning the country music establishment and their hard-partying lifestyle.

As a kid, Jennings learned to play the guitar. At the age of 12, he was already playing in a band and working as a radio DJ. In 1954, Jennings dropped out of school and relocated to Lubbock. There, he obtained employment at a small radio station, KLLL, where he met and became friends with the rock and roll pioneer Buddy Holly. Holly produced Jennings’ debut record, “Jole Blon,” in 1958, and Jennings was a member of Holly’s backup band, The Crickets. He was scheduled to board a private jet with Holly following the group’s performance at the Surf Ballroom in Clear Lake, Iowa on February 3, 1959. Jennings, though, handed up his seat on the plane to ailing rock musician J.P. Richardson, better known as “The Big Bopper.” The plane crashed shortly after takeoff, killing Holly, Richardson, singer Ritchie Valens, and the pilot.

After the disaster, Jennings went to Lubbock and worked as a radio disc jockey for a while. In 1960, he relocated to Phoenix, Arizona, and relaunched his musical career by creating the Waylors. The band built a local fan base and even released songs on the indie record label Trend.

Despite the band’s lack of financial success, Jennings signed with A&M Records in 1963 and relocated to Los Angeles, California. He had a disagreement with the record label on the direction of his music. They desired that he adopt a more pop sound. Jennings stayed devoted to his country style despite opposition. He only released one record for A&M.

Country Star

Jennings relocated to Nashville in 1965. He became housemates with the black man of country music, Johnny Cash, initiating a lifetime friendship. “Stop the World (And Let Me Off)” was Jennings’s first country success that year. In 1968, he had many hit songs, including “Walk On Out of My Mind” and “Only Daddy That’ll Walk the Line.” Jennings received his first Grammy Award in 1969 for Best Country Performance by a Duo or Group with Vocals for his collaboration with the Kimberlys on “MacArthur Park.”

Jennings’ musical approach began to grow during this period, becoming harder and more bass-driven. He collaborated on tunes with Kris Kristofferson and Willie Nelson, among others. Honky Tonk Heroes, which Jennings released in 1973, is commonly regarded as one of his earliest albums to feature his new so-called outlaw sound. This new sound was a marked departure from the polished products of conventional country music, and it began to create its own fan base. “This Time” was the first number-one country success for Waylon Jennings in 1974, and it was immediately followed by “I’m a Ramblin’ Man”

Crossover Success

In 1975, Jennings experienced his first crossover breakthrough when “Are You Sure Hank Done It This Way” entered the mainstream charts. Around the same time, the Country Music Association recognized him as Male Vocalist of the Year. Jennings’ contribution to the 1976 compilation Wanted! The Outlaws aided in his ascent to even greater prominence in the music industry. This recording topped the pop album charts and contained songs by Jennings, Nelson, Tompall Glaser, and his fourth wife, Jessi Colter. Even more, the duo performed many duets, including a version of “Suspicious Minds.”

Together with Nelson, he recorded the 1978 album Waylon & Willie, which went on to sell millions of copies. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” hit the top of the charts and earned Jennings his second Grammy Award. He shared the award for Best Country Vocal Performance by a Duo or Group with Nelson.

Jennings continued to produce songs throughout the remainder of the 1970s and into the early 1980s, including “Luckenbach, Texas (Back to the Basics of Love)” and “Theme from ‘The Dukes of Hazzard’ (Good Ol’ Boys). In addition to composing the theme song for the television series, Jennings acted as the narrator for The Dukes of Hazzard, a country comedy.


Jennings’ drug usage grew into a costly cocaine and amphetamine habit, which cost him up to $1,500 per day. He chose to resign in 1984. The next year, Jennings formed the Highwaymen alongside Kristofferson, Cash, and Nelson. “Highwayman,” which was included on their popular album of the same name, topped the country charts. The 1990 follow-up album, titled Highwayman 2, was not as successful.

Although it was difficult for him to get his music broadcast on country music stations, Jennings remained a popular performer, traveling widely until 1997. Even on the 1996 Lollapalooza tour, more renowned for presenting alternative rock artists, he played a few gigs. In Waylon: An Autobiography, written at this time with Lenny Kaye, Jennings frankly recounts his numerous ups and downs.

In his later years, after being diagnosed with diabetes in the early 1990s, Jennings had difficulty walking. However, this did not prevent him from creating music. Jennings taped four concerts at the Ryman Auditorium in Nashville for the CD Never Say Die Live in 2000. 2001 saw his induction into the Country Music Hall of Fame. Due to diabetes-related bad health, Jennings had to have a foot amputated later that year.

Legacy and Death

Jennings passed away at his home in Chandler, Arizona, on February 13, 2002. He and Colter have been married since 1969 and have one kid, Waylon Albright “Shooter” Jennings. Jennings had five other children from three prior marriages.

Friends and admirers alike lamented the country music superstar’s loss. Kristofferson told the Los Angeles Times that Waylon Jennings was an American figure, a villain with a large heart. Despite his challenging final years, his son Shooter told People magazine, “he was full with creativity and love.”

Shooter Jennings has played in a variety of bands, just like his father. With the help of his backup band, the.357s, Johnny compiled an album of his father’s recordings made years before Waylon’s death. Waylon Forever was released on record in October 2008.

While you are here, if you want to learn about the folk singer: Woody Guthrie, click here.

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