As if they weren’t iconic enough as individuals, Johnny Cash, Waylon Jennings, Kris Kristofferson, and Willie Nelson formed a group in 1985. It was almost like a myth come to life, these four country music legends combining their talents and setting aside their egos.
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Highwayman, the first album to arrive from that partnership, proved this “supergroup” wasn’t just doing it for the publicity or the money. They were doing it out of friendship, and to put a spotlight on the kind of music that meant the world to them.
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It’s not like the four men who comprised what would eventually be known as The Highwaymen were complete strangers when they decided to record together. Their careers were intertwined due to their similar qualities: inimitable voices, stellar songwriting, a commitment to authenticity in the music they made, and the occasionally tumultuous nature of their personal lives. They were friendly long before the Highwayman album.
They unofficially united in Switzerland, of all places, in late 1984 for Cash’s yearly Christmas television special. When they were hanging out and playing songs together, they found the power of their vocal blend was something they couldn’t have quite predicted. The seeds for a collaboration were planted.
It was during that get-together that Marty Stuart, himself a country legend, reminded the quartet about the song “Highwayman.” Jimmy Webb had written it in the ’70s, and up to that point it was mostly known from a cover by Glen Campbell.
Realizing the song’s four verses, each coming from the perspective of a separate persona attached to the narrator’s past lives, were a perfect fit for what they were considering, the four were off and running. Chips Moman, who had worked on a few of Nelson’s ’80s records, was tabbed as the producer, and song ideas were soon being bandied about.
The 1985 debut album Highwayman was credited to all four men. (They wouldn’t officially take on the name The Highwaymen till years later.) In no time at all, the title track surged to No. 1 on the country charts, and the album soared as well. Considering that only Nelson had been enjoying much recent commercial success in his solo career coming into the project, the timing was ideal, both for the performers and for the country music audience longing for more substance than what they were hearing on the radio at the time.
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It’s kind of eerie that Jimmy Webb didn’t write the song “Highwayman” for these guys, so ideally did it fit their artistic approach and performing personalities. With that as the kickoff, Highwayman the album could have been filled with easygoing filler and it would have done just fine. But these four guys dug deep to find songs of similar quality and impact.
They did so by going off the beaten path a bit. “Desperados Waiting for a Train” was a cult outlaw country track from the Guy Clark catalog, but these guys turned it into a standard. Their touching take on Woody Guthrie’s “Deportee (Plane Wreck at Los Gatos),” which gets an assist on vocals from Johnny Rodriguez, showed off their empathetic tendencies.
The theme the album hits pretty hard is that these guys were the last of a figuratively dying breed, both of performers and men. That approach can get a tad overbearing on tracks like “The Last Cowboy Song” or “Against the Wind.” What works better is when the stories are lived-in and specific (Cindy Walker’s “Jim, I Wore a Tie Today,” which Cash and Nelson milk for every last tear) or slyly humorous (John Prine and Steve Goodman’s “The Twentieth Century is Almost Over”).
Highwayman begat two more albums from the group and many live shows over the years. Sadly, only Willie Nelson remains with us out of the four. But the music they made together, especially on the striking debut that almost immediately forced its way into the country music firmament, managed to burnish their already towering legacies.
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Photo by Rob Verhorst/Redferns
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