The Highwaymen were a 1960s "collegiate folk" group. They originated at Wesleyan University and had a Billboard #1 hit in 1961 with "Michael Row the Boat Ashore", a version of the African-American work song, and another Top 20 hit in 1962 with "Cotton Fields". . “Because they all came from the same ilk and knew each other and made a career together, they were all close friends. “It came out of pure friendship,” she says. “Kris was always crazy about Waylon. A quote from his 1996 autobiography appears in the liner notes to The single "Highwayman", a Jimmy Webb composition, became a #1 country hit.
A New Tribute Band Featuring Roger Hegyi as TrueWillie! The first album, Highwayman, was credited to "Nelson, Jennings, Cash, Kristofferson". Their remake of Guy Clark's "Desperados Waiting for a Train" reached the Top 20.