Entertainment Music Country Music 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 By Brendan Le Brendan Le Brendan Le is an Editorial Assistant at PEOPLE with three years of experience working as an editor and writer. People Editorial Guidelines Updated on September 30, 2024 05:35PM EDT Comments Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson onstage at Central Park SummerStage in New York City on May 23, 1993. Photo: Jack Vartoogian/Getty 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. 01 of 07 Band Together Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson perform at a Fourth of July picnic on July 4, 1985 in Austin, Texas. Beth Gwinn/Getty Nelson, Kristofferson, Cash and Jennings had a brotherhood in The Highwaymen. 02 of 07 Fall in Line The Highwaymen perform in Rotterdam on April 20, 1992. Rob Verhorst/Redferns As four guitar-wielding powerhouses of the genre, they performed together for 10 years. 03 of 07 British Air The Highwaymen in London in 1992. Dennis Stone/Shutterstock And they traveled together, too, heading across the pond to London in 1992. 04 of 07 Group Portrait The Highwaymen take a photo for 'Late Night with David Letterman' in May 1995. Wyatt Counts via AP They also performed on talk shows including Late Night with David Letterman... 05 of 07 Legends Live The Highwaymen perform on 'The Tonight Show with Jay Leno' in N.Y.C. on May 30, 1995. Margaret Norton/NBCU Photo Bank/NBCUniversal via Getty ...and The Tonight Show with Jay Leno. 06 of 07 Forever Four The Highwaymen onstage in October 1985. AP Photo/Mark Humphrey 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. 07 of 07 One Last Time Willie Nelson and Kris Kristofferson rehearse for the 56th Grammy Awards on Jan. 24, 2014 in L.A. Kevin Winter/WireImage Nelson and Kristofferson reunited for a performance during the 2014 Grammys along with Merle Haggard and Blake Shelton. Close