In 1985, a remarkable performance of “Me and Bobby McGee” aired, featuring the legendary trio of Johnny Cash, Willie Nelson, and Kris Kristofferson. This show was special because it portrayed Willie Nelson in the starring role, embodying the character of “Bobby” in the song’s narrative.

Johnny Cash, Kris Kristofferson & Willie Nelson - Me & Bobby McGee (1985) - YouTube

Originally written by Kristofferson, “Me and Bobby McGee” tells a poignant story of love, freedom, and loss. The performance by these country icons brought a unique dimension to the song, as they infused it with their own lived experiences and musical artistry.

Alabama Public Television on X: "Join Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson for this live concert recorded in 1990. The Highwaymen perform classics like "Big River," "Me and Bobby

The collaboration between these three legends in this performance highlighted their chemistry and storytelling abilities, making it a standout rendition. It aired during a period when country music’s crossover appeal was growing, showcasing how timeless songs could be elevated by the authenticity of the artists performing them. While Janis Joplin’s version is often the most recognized, this performance gave country fans a rare treat, blending Nelson’s laid-back vocal style with Cash’s deep baritone and Kristofferson’s songwriter’s touch.

Willie, Waylon and the Boys: the Ultimate Outlaw Country Primer - The New York Times

This live collaboration paved the way for future projects by the three, most notably their work as part of the country supergroup, The Highwaymen.