There are two artists that shared this name 1. The Highwaymen were a country supergroup comprising of four musicians well-known for their pioneering influence on the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson. 2. The Highwaymen were a collegiate folk group from the 1960s who had a significant impact on the folk scene of that time and remain famous for the song "Michael" and "Cotton Fields." Formed in 1958 while the band members were at college, the group broke up in 1964 after releasing eight albums and ten singles.