What bound the Johnny Cash, Waylon Jennings, Kris Kristofferson, and Willie Nelson together? Was it a deep passion for storytelling? A mutual respect for one another’s work? Or an almost-innate impulse to do exactly the opposite of whatever the Nashville establishment told them? According to Rosanne Cash, it was pure, simple friendship that led to the creation of the Highwaymen, country music’s original supergroup.
Wildly impressive on their own, the four artists combined were an unstoppable force when they made their onstage debut on this day (July 4) in 1985 during Nelson’s annual Fourth of July Picnic in Austin, Texas.
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The “On the Road Again” crooner hosted his first Independence Day gathering in 1973.
A decade later, the event had blossomed into a full-blown cultural phenomenon, with tens of thousands of fans descending on the Lone Star State’s capital city to celebrate freedom with Nelson and a revolving door of country music collaborators. The 1985 performance also included appearances from Neil Young, Hank Snow and June Carter Cash.
Just months later, Cash, Jennings, Kristofferson, and Nelson released Highwayman, introducing the now-iconic title track and establishing the quartet as one of country music’s greatest artistic experiments.
How Did The Highwaymen Get Their Start?
In today’s modern era, an act like the Highwaymen could easily come across as a publicity stunt. However, the children of the outlaw country titans insist the process was entirely organic.
“It came out of pure friendship,” Rosanne Cash told Rolling Stone in 2016. “There was no marketing guy who came and said, ‘This will be a good idea.’ My dad and Waylon were roommates in the Sixties, hiding their drugs from each other. Kris is like his little brother for decades… They were all buddies and they wanted to do it.”
Added Waylon’s son, Shooter Jennings, “Those guys really loved each other. Because they all came from the same ilk and knew each other and made a career together, they were all close friends. That’s where the magic was. It wasn’t an awkward pairing or like working with someone they didn’t know.”
The concept of the Highwaymen had materialized a year earlier, when Cash talked the other three into filming his Christmas special in Montreux, Switzerland. The foursome would unwind after long days on set by jamming together at their hotel.
“I’m Kinda Amazed I Wasn’t More Amazed”
Between 1985 and 1995, the Highwaymen released three albums. They continued performing together until the late ’90s, when both Cash and Jennings’ health began to deteriorate. Jennings died in 2002; Cash in 2003.
Today, Nelson, 93, is the only living member, as Kristofferson died in 2024.
The late singer-songwriter reflected on his time with the Highwaymen in 2010, saying, “I just wish I was more aware of how lucky I was to share a stage with those people. I had no idea that two of them would be done so soon. Hell, I was up there and I had all my heroes with me. These are guys whose ashtrays I used to clean. I’m kinda amazed I wasn’t more amazed.”
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