In the world of country music, few collaborations have been as legendary as The Highwaymen. This outlaw country supergroup—Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson—united four of the genre’s most rebellious pioneers.
From 1985 to 1995, they recorded three major albums, headlined massive tours, and cemented their place in country music history. Their signature song, Highwayman, topped the charts and became an anthem for independent spirits everywhere.
Though the supergroup is no more, Willie Nelson is still keeping the outlaw tradition alive with a stacked 2025 tour schedule featuring stops across the U.S.
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How The Highwaymen Redefined Country Music
The Highwaymen weren’t just a band—they were a movement. By the 1980s, country music had become increasingly polished and commercialized. The four men, each a legend in his own right, pushed back against that trend.
Their 1985 debut album, Highwayman, was a runaway success, led by the title track written by Jimmy Webb. The song, which tells the reincarnating stories of four wandering souls, became their signature hit, reaching No. 1 on the country charts.
They followed up with Highwayman 2 (1990) and The Road Goes on Forever (1995), delivering raw, rebellious country storytelling that stayed true to their outlaw roots. Though their time as a group was limited, their impact was immeasurable.
Unforgettable Highwaymen Moments
Beyond their music, The Highwaymen delivered some of country’s most iconic moments on stage and in the studio.
“Highwayman” Takes Over the Charts (1985)
When Highwayman hit number one, it wasn’t just a chart victory—it was a declaration that outlaw country still had a place in the industry. The song’s eerie, reincarnation-driven lyrics (with each singer taking on a different life) made it one of the most unique country hits of all time.
Their First Major Tour (1990)
In 1990, The Highwaymen launched a massive world tour, proving that outlaw country was alive and well. The chemistry between Cash’s deep baritone, Waylon’s rugged drawl, Willie’s unmistakable phrasing, and Kris’s storytelling created an unforgettable experience.
Waylon’s Hilarious Stage Banter
Waylon Jennings was known for his quick wit, and his humor often shone through during The Highwaymen’s performances. His sharp one-liners and playful banter with Willie, Johnny, and Kris showcased the camaraderie and bond that made the group so beloved by fans.
Their Hollywood Moment: Stagecoach (1986)
The Highwaymen weren’t just musicians—they were movie stars, too. In 1986, they starred together in Stagecoach, a remake of the 1939 Western classic. While the made-for-TV film wasn’t a massive box-office hit, it solidified their larger-than-life cowboy personas.
The Highwaymen’s Final Ride: A Farewell That Defined an Era
The Highwaymen’s final studio album, The Road Goes on Forever, released in 1995, was more than just a title—it was a testament to their enduring legacy. Their last known performance together occurred at Farm Aid VI on April 24, 1993, in Ames, Iowa.
While not officially a farewell, this performance was among their last times sharing the stage, making it a poignant moment for fans. As health issues began to take a toll—particularly for Johnny Cash and Waylon Jennings—the possibility of future reunions diminished. Jennings passed away in 2002, followed by Cash in 2003, marking the true end of an era.
The Highwaymen: Storytellers Beyond the Stage
The Highwaymen weren’t just recording artists—they also brought their legendary voices to Western storytelling. Between 1996 and 1998, Willie Nelson, Johnny Cash, Kris Kristofferson, and Waylon Jennings contributed to the Louis L’Amour Collection, a four-CD box set featuring dramatizations of seven stories by the renowned author.
Nelson narrated six of the stories, while all four members fully dramatized the seventh, Riding for the Brand. These ventures showcased their talents beyond music, blending their outlaw personas with the rich tradition of Western folklore.
Willie Nelson: Keeping the Spirit of the Highwaymen Alive
Though Cash, Jennings, and Kristofferson have passed on (Kristofferson in 2024 after retiring from music in 2021), Willie Nelson continues to tour and record, carrying the torch for outlaw country.
In 2025, Nelson will embark on another leg of his “On the Road Again” tour, including solo shows and Outlaw Music Festival dates with Bob Dylan, Billy Strings, and more.
Upcoming Tour Highlights:
- April 10: Brandon, MS – Brandon Amphitheater
- April 15: Gautier, MS – The Sound Amphitheater
- May 13: Phoenix, AZ – Outlaw Fest (with Bob Dylan, Billy Strings)
- June 20: Clarkston, MI – Outlaw Fest (with Nathaniel Rateliff, Trampled by Turtles)
- July 4: Austin, TX – Willie’s 4th of July Picnic
For the full 2025 tour schedule and tickets, visit Willie Nelson’s official website.
A Legacy That Still Rides On
The Highwaymen were more than a band—they were four legends who changed country music forever. Their music celebrated freedom, rebellion, and storytelling, setting the stage for today’s outlaw country artists.
And with Willie Nelson still carrying the flag, the spirit of The Highwaymen is far from gone.
