The Highwaymen: The Fights and Friendship of Country’s Great Supergroup
When the Highwaymen recorded “Desperados Waiting for a Train,” written by visionary songwriter Guy Clark, who died earlier this week, the supergroup of Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson landed on their most poignant song. While Jimmy Webb’s “Highwayman” may have been the foursome’s signature, Clark’s “Desperados,” released on their 1985 debut album, dovetailed with their own outlaw legacy: that of aging icons who indulged the young guns their bravado while still beating them on the draw. They may not have been pushing 80 as in Clark’s lyrics (all four were only in their late 40s or early 50s), but, especially now, it’s impossible to think of the Highwaymen as anything but elder statesmen of country music.
“They need to be up there on the big rock with the presidents,” says Emmylou Harris, echoing a sentiment near the end of “Desperados Waiting for a Train”: “to me, he’s one of the heroes of this country,” goes the line, sung by Cash.
The group’s heroics on the concert stage are celebrated today with the release of The Highwaymen Live – American Outlaws, a new three-CD box set that captures the band onstage, chiefly during a 1990 show on Long Island, New York. There’s also a DVD/Blu-ray of that same concert. It’s a fascinating package, testament to each man’s individual output and what they were able to accomplish as a whole.
“Yes, they are the country supergroup, but it was founded by friendship. And it’s the honesty and the purity of that friendship that made the Highwaymen stand out,” says John Carter Cash, who as the son of Johnny Cash and June Carter Cash witnessed the birth of the group firsthand. “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.”
“Those guys really loved each other,” echoes Waylon’s son Shooter Jennings, who also spent some of his formative years on the road with the Highwaymen. “Because they all came from the same ilk and knew each other and made a career together, they were all close friends. That’s where the magic was. It wasn’t an awkward pairing or like working with someone they didn’t know.”
Rosanne Cash, Johnny’s daughter with first wife Vivian Liberto, reinforces the underlying bond of the band. “It came out of pure friendship,” she says. “There was no marketing guy who came and said, ‘This will be a good idea.’ My dad and Waylon were roommates in the Sixties, hiding their drugs from each other. Kris is like his little brother for decades. . . They were all buddies and they wanted to do it.”
The idea for the Highwaymen came about in 1984 when Cash wrangled Nelson, Kristofferson and Jennings to film Cash’s Christmas special in Montreux, Switzerland. Inspired by the camaraderie in the hotel, where they’d jam after long days on the set, the artists returned to the States and entered the studio with producer Chips Moman, eventually taking Webb’s “Highwayman” as both their name and the title of the album. “It was a creative formula that worked,” says John Carter Cash, who recalls Glen Campbell, Marty Stuart and Johnny Rodriguez present during those early sessions. Rodriguez, in fact, would lend his voice to the LP’s “Deportee (Plane Wreck at Los Gatos),” a Woody Guthrie song.