Introduction
The Untold Story of Country Music Legends: The Highwaymen
In 1985, four icons of country music — Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson — came together to form the supergroup The Highwaymen. Over the next decade, with three albums and several world tours, they thrilled fans across the globe — before vanishing like ghost riders in the sky. This is the story behind the music: the untold truth of The Highwaymen.
A Chance Encounter That Changed History
It all began during Christmas of 1984 in Switzerland. Marty Stuart, who was part of Johnny Cash’s band and also his son-in-law at the time, was present for the filming of a Christmas TV special featuring Cash, Willie, Waylon, and Kris. After the show, the four legends jammed together at the hotel — a spontaneous moment that sparked the idea of forming a group.
For Johnny Cash, whose career had been declining, this project was a new glimmer of hope. It was Stuart who suggested they record the song “Highwayman,” a tune with four verses — perfect for four distinct voices and no need for complex harmonies. The song became a major hit, winning a Grammy Award in 1985 and becoming the group’s only No. 1 single.
Naming the Band and a Legal Dispute
Initially, the group had no official name. Their first album simply listed their individual names and the title Highwayman. But when they began touring in 1990, they needed a proper name — and chose The Highwaymen, inspired by their hit song.
However, this led to a legal issue. A folk group from the 1950s and ’60s already went by the name The Highwaymen and filed a lawsuit. Fortunately, the dispute was resolved amicably — the folk group dropped the lawsuit in exchange for the opportunity to open for the new Highwaymen at a Los Angeles concert.
Brotherhood with Friction
Although often seen as a tight-knit group of old friends, the relationships among the members varied. Johnny and Waylon were close, as were Waylon and Willie, and Johnny and Kris. But Johnny and Willie barely knew each other before their collaboration.
According to Roseanne Cash, Johnny’s daughter, the group was born out of genuine friendship, not marketing strategy. “My dad and Waylon were roommates in the ’60s, hiding drugs from each other. Kris was like a little brother. They were all just good friends who wanted to do something together,” she said.
Like brothers, though, they also clashed. Shooter Jennings, Waylon’s son, recalled small fights — like arguing over who got to sing more songs. A notable point of tension was Kris Kristofferson’s outspoken political views, which clashed with the more conservative Waylon. According to Jennings’ widow Jessi Colter, Waylon believed politics didn’t belong on stage — but he still respected Kris, and their differences were met with understanding, not division.
The End of the Road
After the huge success of their 1985 debut, the follow-up albums Highwayman 2 (1990) and The Road Goes On Forever (1995) did not achieve the same commercial impact. Waylon Jennings passed away in 2002 due to complications from diabetes, marking the official end of the group. Johnny Cash followed in 2003, also due to health issues linked to diabetes.
In 2016, Columbia Legacy released a box set titled The Highwaymen Live: American Outlaws, showcasing some of their most memorable performances. In the PBS documentary The Highwaymen: Friends Till the End, Nelson and Kristofferson reflected on their time with the band.
“For me, it was heaven,” Kristofferson said. “I was on stage with my heroes. We did only what we wanted to do, and we stood for what we believed in. That made life beautiful.” Willie Nelson echoed the sentiment: “I had three of my favorite people up there. I loved them like brothers. We got along, had fun, made a movie, toured the world — it was some of the best times of my life.”