Behind the Band Name: The Highwaymen

Country music saw a shift in the 1970s when an outlaw movement blew through Music City and turned Nashville on its rhinestoned head. Major players of the said movement included Johnny Cash, Waylon Jennings, Willie Nelson, Kris Kristofferson, and several others. They fought for their own sound, one that strayed away from, and at times defied, what had been deemed commercially successful in country music at the time.

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Years down the line, the four country stars—Cash, Jennings, Nelson, and Kristofferson—would join forces and form a supergroup for the ages: The Highwaymen.

Behind the Name

Despite the name, these artists were not secretly robbing travelers of the Wild West, quite the opposite. They gave back to the weary and wandering with songs that offered profound wisdom and unshakable hope. Instead, their name came from their signature song, “Highwayman,” which was originally a heady Jimmy Webb ballad about reincarnation.

Appearing on their 1985 debut album, Highwayman, the song became their first No. 1 hit together and would eventually be recognized as their trademark. Tinged in existentialism, the song was the ideal introduction to the supergroup—and, in turn, the perfect name for them, as well— as it harkened back to their days fighting convention and grappling with the mainstream as country’s outlaws.

Dubbing themselves The Highwaymen seemed fitting, however, a band with the same name, a ’60s-era folk group, already existed. In 1990, the original Highwaymen sued the supergroup over the use of their name, but would later drop the suit once they all reached an agreement about who owned the name and how it could be used.

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And with that, The Highwaymen were able the ride again. Together from 1985 and 1995, the supergroup recorded three albums as The Highwaymen: Highwayman, Highwayman 2, and The Road Goes on Forever. Cash, Jennings, Nelson, and Kristofferson all have their own impressive catalogs, but they no doubt made magic together as The Highwaymen.

Photo by Rob Verhorst/Redferns