Highwaymen—the supergroup dubbed the Mount Rushmore of country music—came together when Willie Nelson, Waylon Jennings, and Kris Kristofferson joined Johnny Cash on his 1984 Christmas TV special. ∙ Cash’s guitar player, Marty Stuart, had played Glen Campbell’s cover of Jimmy Webb’s “The Highwayman” for the group—giving them their signature song. ∙ Their 1985 debut, helmed by legendary producer and songwriter Chips Moman, topped the Country chart, went Platinum, and picked up a Grammy nomination. ∙ The group’s cover of “Desperados Waiting for a Train” landed in the Top 20, at long last making an honest hit out of Guy Clark’s classic song. ∙ Highwayman 2, released in 1990, spent 40 weeks on the Country chart and was nominated for a Grammy. ∙ Kristofferson and Nelson celebrated the group at the 2013 Grammy Awards, with Merle Haggard and Blake Shelton sitting in for their late bandmates in a three-song medley.