Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson, often referred to as "The Highwaymen," were iconic figures in the development of outlaw country music, a subgenre that rejected the slick production of the Nashville sound in the 1970s and 1980s. Their music is characterized by raw, honest lyrics, a distinctive blend of country and rock, and a rebellious spirit. Each member had a successful solo career prior to their collaboration, with signature songs like Cash's "Ring of Fire", Nelson's "On the Road Again", Jennings' "Luckenbach, Texas", and Kristofferson's "Me and Bobby McGee". Their collective impact on the music industry has been profound, influencing a generation of country musicians and songwriters.