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The Highwaymen Return

How the 1980s supergroup revived four careers — and country music itself

(Video) The Highwaymen: Friends Til The End Movie Trailer: The pioneering outlaw country music supergroup featured Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson.

More than 30 years ago, four country music icons — Kris Kristofferson, Johnny Cash, Waylon Jennings and Willie Nelson — gathered to record an album, Highwayman. Their project was far from a surefire hit: The "outlaw" country music they'd pioneered in the 1970s had faded away, victim to a slicker crossover sound (think Urban Cowboy).

Yet the chemistry among the musicians couldn't be denied. "You wouldn't think that our four uneven voices would blend," Nelson has said. "But they did." Mickey Raphael, who played harmonica on the album, recalls the men's differing styles. "Johnny was bigger than life. Kris was the revolutionary, and Willie was the jokester," he says. "Waylon was the conscience of the whole thing, very intense, the one who said, 'Don't screw this up.'"

 The Legacy of the Highwaymen

Paul Spella

The Highwaymen: Kris Kristofferson, Johnny Cash, Waylon Jennings and Willie Nelson

The others must have listened to Jennings. The album sold a million copies, leading to two follow-ups for the supergroup, who became known as the Highwaymen. Songwriter Jimmy Webb was blown away when he heard the cover of his title tune, in which each singer took on the role of a different character: “You couldn’t imagine better casting than that. They fleshed out the song and made it walk and talk.” The left-field hit was a vindication for counterculture country as well as for its leaders. Says filmmaker Jim Brown, who directed the new documentary The Highwaymen: Friends Till the End, "It shows that even if the powers that be don't think you're valuable, you still are."

AARP is the sponsor of The Highwaymen: Friends Till the End, which premieres on PBS on May 27.