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The Highwaymen: Country’s Outlaw Supergroup

October 29, 2026 1

Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson. Four legends, three albums, and one of the most famous lineups in music history. From our guide to country music artists.

The Highwaymen at a glance

Members	Johnny Cash, Waylon Jennings, Willie Nelson, Kris Kristofferson
Active	1985–1995
Albums	Highwayman (1985), Highwayman 2 (1990), The Road Goes On Forever (1995)
Signature song	“Highwayman”, written by Jimmy Webb

How it came together

The four had been friends and collaborators for years, central figures in the outlaw country movement that fought Nashville’s polished sound in the 1970s. In 1984, while recording a Christmas special in Switzerland, they cut a few songs together. The result, Highwayman (1985), topped the country albums chart.

"Highwayman"

The title song, written by Jimmy Webb, gives each member a verse as a different soul across time: a highwayman, a sailor, a dam builder and a starship captain. It became a No. 1 country hit, and Webb won a GRAMMY for Best Country Song.

Essential Highwaymen songs

“Highwayman” – Four lives, one soul.
“Desperados Waiting for a Train” – Guy Clark’s story of an old friend.
“Big River” – A Johnny Cash classic, shared.
“Silver Stallion” – A restless outlaw anthem.
“The Road Goes On Forever” – Robert Earl Keen’s crime ballad.

Their place in country history

The Highwaymen were outlaw country’s victory lap. Read about the outlaw movement in our history of country music.

If you like The Highwaymen

Try the Nitty Gritty Dirt Band, who brought rock and roots together, and George Strait, who carried traditional country into the ’80s.

Highwaymen FAQs

Who were the Highwaymen?

Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson.

How many albums did the Highwaymen make?

Three: Highwayman (1985), Highwayman 2 (1990) and The Road Goes On Forever (1995).

Who wrote "Highwayman"?

Jimmy Webb.

Sources

Country Music Hall of Fame · Recording Academy

How we report: Facts on this page come from the sources listed above and are checked by a second editor. Read our editorial standards. Spot an error? Tell us.