The Highwaymen Highwayman on Limited Edition 180g LP - The Highwaymen - Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson - were country music's first bonafide "supergroup," an epic quartet of blockbuster star power comprised of the four prime forces of America's outlaw country music revolution. An essential musical and cultural influence, the Highwaymen were active for the decade spanning 1985 to 1995, recorded three major label albums (Highwaymen (1985), Highwaymen 2 (1990) and The Road Goes On Forever (1995)), charted hit singles (including their No. 1 debut, "Highwayman," which won the Best Country Song Grammy Award in 1986) and performed a variety of shows achieving mythic status for those lucky enough to have been there.