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The Highwaymen: The Fights and Friendship of Country’s Great Supergroup

A new box set captures the electrifying live show of Waylon Jennings, Johnny Cash, Willie Nelson and Kris Kristofferson

The HighwaymenThe Highwaymen

A new live box set captures the Highwaymen onstage in 1990.

Jim McGuire

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.

“They came together as friends, and that’s the unifying power of the Highwaymen”

Darius Rucker is a passionate fan of that first Highwayman album (they’d follow it up with Highwaymen II in 1990 and 1995’s The Road Goes on Forever) and says the four stars uniting for such a high-profile project was actually a creative risk. “They showed people that four really big superstars can get together and make something great. That record could have been awful, but it wasn’t,” he says. “They worked together and left their ego at the door and said, ‘Let’s make some country music.’ And we’re still talking about them today.”

The new American Outlaws set was painstakingly produced and curated by Nelson’s long-time harmonica sideman Mickey Raphael, who also toured with the Highwaymen band, an all-star collective that included steel guitarist Robby Turner, now with Chris Stapleton. Onstage, the Highwaymen’s live shows were a veritable legends jukebox, with each member taking a turn in the spotlight to play their hits. “You had Cash doing ‘Big River’ and then Willie doing ‘Always on My Mind.’ It blew people’s minds,” says Jennings.

Both of those songs appear here, along with some lesser-known gems that rise to the surface. The ensemble “The Last Cowboy Song” is a hypnotic elegy, Cash’s spoken-word “Ragged Old Flag” unfurls with grace and subtle patriotism, and Nelson’s take on Kristofferson’s “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” is dazzling.

Along with American Outlaws, and a new greatest-hits disc, The Very Best of the Highwaymen, also out May 20th, the band is the focus of PBS’s American Masters. Titled The Highwaymen: Friends Till the End, the installment premieres Friday, May 27th, on PBS, and tells the group’s origin story, while delving into the relationships of its members. At times, it could be a contentious union, especially when it came to the conflicting ideologies of Kristofferson and Jennings.

“Kris was very much into politics. Waylon never believed that you should use that platform of entertainment [for that], so that really chafed him, but he understood Kris, and Kris understood him,” says Jessi Colter, Jennings’ widow. “Kris was always crazy about Waylon. Waylon was knocked to his knees when he first heard Kris’s songs. They were hanging out in L.A. . . . and then Kris comes to Nashville, and we’re all hanging out on 19th Avenue, driving up and down the streets at night, playing pinball at Bobby Bare’s. It was a loving thing when Kris and Waylon got together, but onstage, when Kris would talk politics, Waylon wouldn’t agree.”

Jennings remembers the disagreements as squabbles among kids. “My dad and Cash would get in a fight and not talk, or they’d get mad at Willie cause Willie had one more song than everybody else,” he says. “They were like brothers up there, bickering with each other.”

Tension often results in great art, however, and on American Outlaws, the performances crackle. Jennings sings with a devilish swagger; Kristofferson, never the most pristine of vocalists, commands with steely determination; Nelson delivers his unconventional quaver; and Cash holds it all together with an imposing gravitas. Somehow, it all gels, on Jennings’ “Are You Sure Hank Done It This Way,” on the Highwayman II cut “Silver Stallion” (Cat Power would later record a version) and even on the George Jones novelty song “The King Is Gone (So Are You).”

“What I’ve always respected about all of those guys was the honesty and the integrity of the songs. Not being scared to say what is on your mind and buck up to the establishment, even if you might not make some people happy or ruffle feathers,” says Ryan Bingham, one of today’s artists who best encapsulates the rebel spirit of the Highwaymen. “But those songs last. Through decades and generations, young kids will be listening to those songs 20 to 30 years from now and will find something to relate to within the message of the tune. It’s something that had a big impact on me, listening to their music.”

Cash seconds Bingham’s assessment, marveling at the longevity of the Highwaymen catalog. “This is something that 200 years from now, it’ll have a greater import than even it does right now. It’ll be more clear, wherefore our tree came from. We’re looking back over the history of our modern recorded music,” he says.

To Harris, the Highwaymen thrived as a unit because of each artist’s refusal to ever be boxed in. The very existence of their “supergroup” was itself a proclamation of their independence: they recorded the songs they liked, whether it was a Guy Clark composition or Bob Seger’s “Against the Wind.”

“Country music does have a tendency to be too constricted or afraid of anything that colors outside the lines,” says Harris. “When you break free of those parameters you really have something to say. And that’s what they did. They just blew it out of the water.”

“All those guys were lone-wolf solo artists, rebels who did what the fuck they wanted to do,” says Rucker. “They said, ‘We’re going to be rebels, but we’re going to rebel together.'”

And, as in Clark’s heartrending “Desperados Waiting for a Train,” they also faced mortality together. “Highwayman” was the band’s theme, says John Carter Cash, but “Desperados” was the group’s heart and soul.

“They had a way of putting themselves in a place of the person singing the song. And that is the magic of ‘Desperados,'” Cash says. “They took it on as being their own story.”

Jennings himself believed that to be true. A quote from his 1996 autobiography appears in the liner notes to American Outlaws. “There’s not one of us who hasn’t come face to face with his own mortality, and many’s the time we’ve gone through our struggles and survivals together,” Jennings wrote. “There’s a blues song that talks about the ‘key to the highway.’ That’s our friendship, unlocking any door that stands between us, and it keeps four very different individuals together.”


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