An Outlaw’s Story: How Waylon Jennings Made A Name And Built A Legacy In Country Music

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Photo credit: The Silhouette Read more at:
Photo credit: The Silhouette

Waylon is among the ranks of outlaw country stars. He’s created 16 hit singles and 11 #1 albums, transforming country music forever.

On February 2, 1959, a young bass player known as Waylon Jennings gave up his seat on a plane that ended up crashing near Clear Lake, Iowa, killing music stars Buddy Holly, J.P. Richardson, and Ritchie Valens. The day would later be remembered as “The Day the Music Died,” but Jennings and his music were given a shot to live.

Jennings’ career actually started in the 1970s, when he joined what was known as the outlaw movement in country music. The movement was formed in resistance to the Nashville sound style, which tried to lessen the honky tonk impact of older country music.

Jennings joined fellow outlaws and major country superstars such as Willie Nelson, Merle Haggard, and Hank Williams Jr., and released numerous hit singles and albums in this genre. His 1976 compilation album with his wife, Jessi Colter, Nelson, and Tompall Glaser, was the very first country album to be certified Platinum by the RIAA.

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In the mid 1980s, Jennings and Nelson teamed up with Johnny Cash and Kris Kristofferson to form the country supergroup, The Highwaymen. Throughout the course of their ten-year career together, the group made a total of three studio albums and had three singles hitting the charts, including the number one hit, “Highwayman.”

In addition to his very successful music career, Jennings also appeared in movies and on television, famously starring as the balladeer and composing and recording the theme song for The Dukes of Hazzard.

In 2000, Jennings started to experience issues with diabetes, which restricted his mobility and kept him from performing as much as he wanted to. Jennings’ diabetes continued to get worse over the course of the next two years, and he eventually died in his sleep on February 13, 2002, at the age of 64.

To pay tribute to Jennings, we’ve listed two of his massive hits, and also a tribute performed by one of his close friends and a modern-day outlaw, who is helping to sustain his awesome legacy.


Originally composed and recorded by Ray Pennington, “I’m a Ramblin’ Man” was released in 1967 and was a chart success, hitting the 29th spot.

Eight years later, Jennings recorded his own rendition of the song, which reached the top spot on the Billboard Hot Country Singles chart, becoming his second number one hit. The song was also a hit in Canada, where it peaked at the second position, and it even made its way onto the charts in Australia.

The song’s lyrics tell the story of a ‘ramblin’ man’ who keeps traveling around the country, never finding a place to settle down. Even though he “Left a girl in West Virginia/Up there where that green grass grows,” and also “Got a girl in Cincinnati/Waitin’ where the Ohio River flows,” he still can’t bring himself to stay put in one place for long.

Since the narrator knows that he will never be able to settle down, he warns anyone who tries to get too close to him, saying “Once I mess with the ol’ mind/Your little ol’ heart won’t be the same.”

In 1975, Jennings took to the stage at the Cowboy Jack Clement Show to perform his hit song “Ramblin’ Man,” which is now regarded as one of his trademark songs.

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