Introduction
The Untold Truth of The Highwaymen: A Country Music Legend
In 1985, four country music legends — Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson — came together to form the supergroup The Highwaymen. Over the course of a decade and three albums, they captivated fans around the world — before fading away like ghost riders in the sky.
It All Began on a Fateful Christmas
It all started during Christmas 1984 when Marty Stuart — Johnny Cash’s son-in-law and member of his band — witnessed a memorable gathering in Switzerland during the taping of the Johnny Cash Christmas Special. Cash, Nelson, Jennings, and Kristofferson jammed together back at the hotel and realized it would be fun to team up for something new. The idea gave Cash — who was going through a rough patch in his career — a much-needed spark of hope.
“Highwayman” – The Defining Song
Initially, harmonizing four very distinct voices was challenging, especially between Cash and Nelson. That’s when Marty Stuart brought in a solution: the song “Highwayman”, with four separate verses for each member — no harmonies required. Cash only asked to sing the verse about the astronaut — and the rest was history.
The song became the group’s one and only No.1 hit, winning the Grammy for Best Country Performance by a Duo or Group in 1985.
Naming Trouble and a Lawsuit
Their first album, Highwayman, was released under their individual names without a group name. But when they went on tour in 1990, they decided to call themselves The Highwaymen, after their hit song and album. However, the name was already taken by a 1950s–60s folk group. A lawsuit followed, but according to the Willie Nelson and Friends Museum, it was peacefully resolved when the folk group agreed to open for The Highwaymen at a concert in Los Angeles.
Friendship, Clashes, and Contrasts
Although remembered as close friends, the relationships within the group were more complex. Some pairs were close — like Johnny and Waylon, or Kris and Willie — but Johnny and Willie barely knew each other before the Christmas special. Still, Johnny’s daughter Rosanne Cash said the group was born out of true friendship, not marketing.
At one point, the group even considered inviting Merle Haggard, a longtime friend of all four, but he turned them down. Like real brothers, they also had their share of arguments. Shooter Jennings, Waylon’s son, recalled small fights — like Cash and Waylon not talking to each other, or complaints that Willie had more songs than the rest.
There were also political differences, especially between Kris Kristofferson, who was very politically active, and Waylon Jennings, who believed that politics had no place in entertainment. Waylon’s widow, Jessi Colter, said they understood each other despite the disagreements, and their bond remained strong.
The End and the Legacy
After the success of their 1985 debut, the 1990 album Highwayman 2 saw less commercial success, and the 1995 release The Road Goes On Forever even less. When Waylon Jennings passed away in 2002, followed by Johnny Cash in 2003, The Highwaymen’s journey officially ended.
In 2016, Columbia/Legacy released a box set titled “The Highwaymen Live: American Outlaws”, featuring some of their most iconic live performances. In the PBS documentary The Highwaymen: Friends Till the End, Willie Nelson reflected: “I was out there with three of my favorite people. I loved them like brothers. We had fun, we toured the world — it was one of the best times of my life.”