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Flashback: See the Highwaymen Perform Their Signature Hit

Willie Nelson enlisted country’s one true supergroup for Farm Aid in 1993

The “supergroup” moniker is tossed around all too freely, but no title better suited the Highwaymen. Made up of Johnny Cash, Waylon Jennings, Kris Kristofferson and Willie Nelson — all of them eventual Country Music Hall of Fame members — the all-star band launched their first-ever concert tour at the Houston Astrodome on this day in 1990.

The four musicians came together in the studio well before that, however. In 1985, they released their debut album Highwayman, named after the Jimmy Webb song that became their signature. And like the “supergroup” label, it fit this gang of outlaws perfectly. The story of four different men at various moments in history — or spirits, if you buy into the reincarnation undercurrent of the lyrics — “Highwayman” opens with Nelson singing about being a bandit, robbing women of their jewelry and murdering soldiers who got in his way. His nasally recollection of “the bastards” who hanged him for his crimes, remains one of the Red Headed Stranger’s most defiant deliveries.

Kristofferson follows, inhabiting the life of a doomed sailor, followed by Jennings and his tale of a dam builder entombed in the massive concrete of Hoover Dam. By the time Cash concludes the ballad, the narrative reaches for the stars with a fantasy about piloting a spaceship across the galaxy. “I’ll find a place to rest my spirit if I can,” he intones, driving home the theme of the endless soul.

“Highwayman” hit Number One in 1985, the band’s only chart-topping single, and it went on to become the centerpiece of the four country icons’ live show, even years later. In 1993, when Nelson enlisted his pals for his sixth Farm Aid benefit concert in Ames, Iowa, they lit into their trademark to thunderous applause. (Watch a video of the performance above.)

“We’ve had a pretty good run,” Cash said onstage. “We’ve been across the country and around the world together.” And despite the passing of Jennings in 2002 and Cash a year later, the supergroup’s legacy, like the wandering ghost of “Highwayman,” will always be around and around and around.

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