In 1984, Johnny Cash was filming the holiday TV special "Christmas on the Road" in Montreux, Switzerland, and he implored some friends and colleagues to join him. They just so happened to be three of the biggest names in country music: Willie Nelson, Waylon Jennings, and Kris Kristofferson. After taping all day, they'd head back to the studio to jam well into the evening, and they realized that they played together so well that they might as well form a supergroup and cut an album, according to Rolling Stone. The first record, released in 1985, wasn't credited to a group but rather Jennings, Nelson, Cash, and Kristofferson, individually.

The project was a landmark country event. Titled "Highwayman," the single of the same name hit No. 1 on the country music charts, and the follow-up, "Desperados Waiting for a Train," hit No. 15. The album's name soon became the group's name (sort of): the Highwaymen. In addition to establishing themselves as the tastemakers and godfathers of modern country music, and laying the groundwork for other monumental collaborations (particularly "Trio," the smash hit one-off by Dolly Parton, Emmylou Harris, and Linda Ronstadt), the Highwaymen became a pop culture machine. The foursome also starred together in the 1986 made-for-TV movie "Stagecoach" and four discs' worth of audio dramatizations of classic Louis L'Amour western stories. In 1990 and 1995, the Highwaymen reconvened to record more albums.

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