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

Mar. 15, 2025

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

Jack Vartoogian/Getty

The Highwaymen made the names as individual artists before creating one of country’s most notable supergroups.Country music pioneersKris Kristofferson,Willie Nelson,Johnny Cashand 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 Foreverwas 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.

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

Country music pioneersKris Kristofferson,Willie Nelson,Johnny Cashand 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 Foreverwas 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.

01of 07Band TogetherWillie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson perform at a Fourth of July picnic on July 4, 1985 in Austin, Texas.Beth Gwinn/GettyNelson, Kristofferson, Cash and Jennings had a brotherhood in The Highwaymen.

01of 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

Beth Gwinn/Getty

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

02of 07Fall in LineThe Highwaymen perform in Rotterdam on April 20, 1992.Rob Verhorst/RedfernsAs four guitar-wielding powerhouses of the genre, they performed together for 10 years.

02of 07

Fall in Line

The Highwaymen perform in Rotterdam on April 20, 1992.Rob Verhorst/Redferns

Rob Verhorst/Redferns

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

03of 07British AirThe Highwaymen in London in 1992.Dennis Stone/ShutterstockAnd they traveled together, too, heading across the pond to London in 1992.

03of 07

British Air

The Highwaymen in London in 1992.Dennis Stone/Shutterstock

Dennis Stone/Shutterstock

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

04of 07Group PortraitThe Highwaymen take a photo for ‘Late Night with David Letterman’ in May 1995.Wyatt Counts via APThey also performed on talk shows includingLate Night withDavid Letterman…

04of 07

Group Portrait

The Highwaymen take a photo for ‘Late Night with David Letterman’ in May 1995.Wyatt Counts via AP

Wyatt Counts via AP

They also performed on talk shows includingLate Night withDavid Letterman…

05of 07Legends LiveThe 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…andThe Tonight Show withJay Leno.

05of 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

Margaret Norton/NBCU Photo Bank/NBCUniversal via Getty

…andThe Tonight Show withJay Leno.

06of 07Forever FourThe Highwaymen onstage in October 1985.AP Photo/Mark HumphreyThe 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 toldRolling Stone.

06of 07

Forever Four

The Highwaymen onstage in October 1985.AP Photo/Mark Humphrey

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 toldRolling Stone.

07of 07One Last TimeWillie Nelson and Kris Kristofferson rehearse for the 56th Grammy Awards on Jan. 24, 2014 in L.A.Kevin Winter/WireImageNelson and Kristofferson reunited for a performance during the 2014Grammysalong withMerle HaggardandBlake Shelton.

07of 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

Kevin Winter/WireImage

Nelson and Kristofferson reunited for a performance during the 2014Grammysalong withMerle HaggardandBlake Shelton.

source: people.com