The Highwaymen were a country music supergroup composed of Willie Nelson, Johnny Cash, Waylon Jennings and Kris Kristofferson. They recorded three studio albums and performed live together from 1985 to 1995. One of their most popular songs was “Me and Bobby McGee”, a cover of a song written by Kris Kristofferson and Fred Foster, and originally recorded by Roger Miller.

“Me and Bobby McGee” tells the story of two drifters who hitchhike across the American South and then part ways in California. The song expresses the narrator’s nostalgia for the freedom and love they shared with Bobby McGee. The song has been interpreted as a tribute to the counterculture movement of the 1960s and 1970s, as well as a reflection on the loss of innocence and idealism.

The Highwaymen performed “Me and Bobby McGee” live at Nassau Coliseum in Uniondale, New York, in March 1990. The performance was part of their American Outlaws tour, which also featured Jessi Colter, June Carter Cash and David Allan Coe as guest artists. The live version of the song was released on their album Live – American Outlaws in 2016. The song showcases the distinctive voices and styles of each member of the group, as well as their harmonies and camaraderie.