The idea to form The Highwaymen came from “pure friendship”, according to Rosanne Cash (Johnny’s daughter). The four talented musicians had been pals for years before they formed the group. It was only when they were all in Switzerland and spending lots of time together filming a Johnny Cash Christmas TV Show that they saw what a great idea it would be. This was in 1984. In 1985, they would have their first collaborative album climbing high in the country charts.
While each musician was incredibly well-respected within the industry, they each had a unique style and personal strengths. While Johnny was the world-famous legend, Willie was the fiercely talented musician. Waylon contributed his amazing singing voice, and Kris his brilliant songwriting chops.
The group took its name from the title track “Highwayman” (a ballad about reincarnation) on their first album Highwayman(1985). The track would become the band’s only number-one hit, later honoured with a Grammy Award. There was, however, a controversy around the group using the name “The Highwaymen”. It turned out that there was already another American folk group with the same name — and they weren’t too happy about sharing. Though the original Highwaymen band tried to sue the supergroup, the case was dropped once Johnny, Waylon, Willie, and Kris invited the band to perform with them on stage in Los Angeles.
After achieving success with their first two albums Highwayman and Highwayman 2, the group started touring together in 1990.
They disbanded in 1995, but the group’s friendships and musical collaborations continued. Even after Waylon sadly died in 2002, and Johnny in 2003, Willie and Kris worked together on music and remained friends.