See the Best Photos of Kris Kristofferson, Willie Nelson, Johnny Cash and Waylon Jennings in The Highwaymen

Country legends Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson formed the country supergroup in 1985

The Highwaymen made the names as individual artists before creating one of country's most notable supergroups.

Country music pioneers Kris Kristofferson, Willie Nelson, Johnny Cash and Waylon Jennings formed the group in 1985. The four musicians had led the formation of the outlaw country subgenre, a rock and roll and blues-inspired sound that departed from Nashville's country-pop sound at the time.

Together, The Highwaymen recorded three albums and had one song that topped the country charts, "Highwayman." Their last LP, The Road Goes On Forever was released in 1995, and the group toured into the late '90s, until Jennings and Cash's health began declining.

Jennings died on Feb. 13, 2002, at age 64 from complications of diabetes. A year later, Cash died on Sept. 12, 2003, at age 71 of complications from diabetes. On Sept. 28, 2024, Kristofferson's family shared in a statement to PEOPLE that the singer had died "peacefully in his home" at 88 years old.

See the best photos of Cash, Kristofferson, Nelson and Jennings in action as the ultimate country supergroup.

Band Together

Nelson, Kristofferson, Cash and Jennings had a brotherhood in The Highwaymen.

Fall in Line

As four guitar-wielding powerhouses of the genre, they performed together for 10 years.

British Air

And they traveled together, too, heading across the pond to London in 1992.

Group Portrait

They also performed on talk shows including Late Night with David Letterman...

Legends Live

...and The Tonight Show with Jay Leno.

Forever Four

The four men always got along, according to Cash's son and daughter, John and Rosanne, as well as Jennings' son Shooter.

"Individually, these gentlemen had their own style, their own thoughts, their own feelings, their own emotion. But they came together as friends, and that’s the unifying power of the Highwaymen,” John told Rolling Stone.

One Last Time

Nelson and Kristofferson reunited for a performance during the 2014 Grammys along with Merle Haggard and Blake Shelton.

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