Formed in 1985, the Highwaymen pulled together four country greats: Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson. Their first single, "Highwayman," shot to the top of the country charts and helped inspire an album of the same name — which also went No. 1. The follow-up single, a cover of Guy Clark's "Desperadoes Waiting for a Train," made it into the Top 20, but the group didn't record together again until 1990. Their follow-up album, Highwayman 2, received a slightly less effusive reception — hitting No. 4 on the country charts — and their third (and final) attempt, 1995's The Road Goes on Forever, was a sales dud. Nonetheless, they are remembered fondly for their star power — even by the stars themselves. "If I'd ever dreamed back when I was a janitor that I would be standing up onstage with those guys and be close friends with all of them," Kristofferson told the Sun in 2008, "I would've thought I'd died and gone to heaven."
Top 10 Supergroups
Gnarls Barkley's Danger Mouse has teamed up with the Shins' lead singer, James Mercer, to create a band called Broken Bells. In honor of the newly formed superduo, TIME takes a look at previous all-star bands