Published On: Wed, Dec 20th, 2017

Classic Album: The Highwaymen – Highwayman

With four true legends collaborating, 1985’s Highwayman album is a true country classic. But at the time, as Country Music reports, it was cut amid faltering careers and brought together four men forced to face their own mortality.


Picture the ideal birthplace for country music’s greatest supergroup and Switzerland is unlikely to figure highly. Yet it was there, in Montreux, that Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson first convened in November 1984. Cash was in town to film a Christmas TV special for CBS and saw it as a perfect excuse to invite some famous pals along.

“It’s more than a one-shot,” Cash had told Nelson beforehand. In his autobiography, My Life, Nelson recalled that Cash added:
“I want the four of us to cut a record together in Nashville before the show airs, so we have something to sell during the holiday season…Hell, Willie, you’ve recorded with everyone in the world except me. Don’t you think it’s time?”

After filming was over in Montreux, the entire cast retired to Cash’s hotel suite, where they jammed and tossed songs back and forth into the small hours. Among the troupe of players was producer Chips Moman, who was keen to oversee a duet recording between Cash and Nelson, his regular charge, once everyone had returned home. But the session in Nashville didn’t quite click. It was only when Jennings and Kristofferson stopped by that the gears began falling into place.

The number that the four chose to perform was an old Jimmy Webb song, Highwayman. Webb had first cut it for a solo album in
1977, after which longtime ally Glen Campbell recorded his own version. Jennings had already been offered the tune some years prior, but “just couldn’t see it then”.

In the studio in Nashville, however, it seemed the perfect vehicle for the assembled quartet. There were four verses and four voices. Fittingly too, Webb’s song essayed the tale of an outlaw from another century who is reincarnated in four distinct phases throughout time – highwayman, sailor, a construction worker and space traveller, the latter flying into the future on “a starship across the universe divide.”

“There were four verses, one for each of us,” Nelson explained. “All I had to do was read the first one to know that the song would work perfectly… You wouldn’t think that our four uneven voices would blend. But they did. They fit together like a jigsaw puzzle.”
Cash immediately called dibs on the astronaut character. “Talk about predestination,” Webb observed to Performing Songwriter in 2012. “I don’t know how they decided who would take which verse, but having Johnny last was like having God singing your song.”

A Union Of Lost Souls
On an existential level, Highwayman tapped into the almost mythic nature of this new union of souls. Cash, Nelson, Jennings and Kristofferson were living legends of country, a bunch of outliers who, in their own different ways, had fashioned successful careers without kowtowing to the establishment. None of them had had it easy, struggling with hardships, addictions and commercial failures along the way.

But, through sheer force of conviction, each had prevailed. The song’s closing lines, delivered with stoic authority by Cash, seemed to capture this indomitable spirit: “Perhaps I may become a highwayman again/ Or I may simply be a single drop of rain/ But I will remain/ And I’ll be back again and again and again…”

“I tell the story that we all got together to try to revive Waylon’s career,” Nelson has said. “And as long as it gets a laugh, I’ll keep telling it.” Despite the jocular tone, there was a degree of truth behind his remarks. Jennings’ cocaine habit had been out of control in the early-80s and the quality of his records suffered as a result. By the time he finally decided to get clean, in the spring of 1984, he’d released a series of mostly lacklustre albums with dwindling sales figures.

But the man most in need of a career boost was Cash. As he would admit in his 1997 autobiography, “I was invisible on the charts” in the 80s. Cash’s record label, Columbia, had grown indifferent to him. And while he remained in the public eye, appearing on
The Muppet Show and Saturday Night Live (spoofing Elton John, dressed in a technicolour cape, pink feather boa and out-sized glasses), Cash’s studio work left much to be applauded.

The lowest point came in 1984, when, probably for reasons best known to himself, he teamed up with producer Billy Sherrill to record Chicken In Black. Its lyrics involved Cash receiving a brain transplant from a criminal, while his old brain is given to a chicken, which is then handed a 10-year recording contract. The song was as baffling as it was embarrassing. Cash even hammed it up in the video as ‘The Manhattan Flash’, complete with superhero outfit. Other recordings made with Sherrill around that time were shelved, only surfacing 30 years later as Out Among The Stars. Cash was still doing well on the road, but he was now reduced to playing ski lodges and casinos.

In short, he appeared lost.Forming The Highwaymen (the name was bestowed up on them) offered Cash a shot at some form of redemption. The quartet’s Jimmy Webb cover proved that, rather than being a redundant force, Cash’s creative talents had hitherto been merely misdirected. The combination of the four voices worked beautifully, the grain of collective experience running through its narrative groove. Cash noted later that “we had so much fun, we decided to make a habit of it.”

The resulting album, simply titled Highwayman, offered a selection of covers (save for a pair of Cash originals) that showcased each of their unmistakable voices, trading verses and gathering together for harmonies. “There’s the four of us standing there, grouped around microphones,” Jennings wrote in his memoir, Waylon: An Autobiography. “I don’t think there are any other four people like us.

John says that we came together because we all have a life commitment to the music. We know the same songs, but we sing them from different perspectives. We can blend the early country of The Carter Family with Texas swing, Southern gospel and rockabilly, and each of us feels comfortable singing real slices of life. 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.”

Of the two Cash tunes, Big River was the better known. He and the Tennessee Two had scored a big hit with the song for Sun Records in 1958, replete with Cash’s trademark boom-chicka-boom sound. The Highwaymen didn’t fiddle with the formula too much, retaining its toe-tapping chug, though they did restore a verse that had been left out of the original.

The intro itself is perfectly weighted. Nelson’s dry tones (“I taught the weepin’ willow how to cry, cry, cry”) give way to Kristofferson’s huskier ones (“And I showed the clouds how to cover up a clear blue sky”), before Jennings steps in (“And the tears I cried for that woman, are gonna flood you, big river”) and Cash brings it to a swift resolution (“And I’m gonna sit right here until I die”).

To hear these four ageing campaigners swap lines with such effortless authority is terrific. Behind them, a crack band of players – among them Marty Stuart [see page 40], guitarist Reggie Young and harmonica wizard Mickey Raphael – keep everything moving with twangy aplomb. The other Cash retread is more muted. Committed To Parkview, inspired by his friend Porter Wagoner’s spell in the Nashville psychiatric hospital of the same name some years earlier, had first cropped up on Cash’s 1976 solo effort, One Piece At A Time.

The Highwaymen made it a double-hander between Cash and Nelson, sensitively portraying a world of lost, broken and forgotten souls. “There’s a man across the hall who sits starin’ at the floor,” sings Cash with a grave omnipotence. “He thinks he’s Hank Williams, hear him singin’ through the door/ There’s a girl in 203 who stops by to visit me/ And she talks about her songs and the star that she should be.”

A similar sense of despondency informs their version of Woody Guthrie’s Deportee (Plane Wreck At Los Gatos). Its lyrics address the real-life air crash near Los Gatos Canyon in California in 1948 that claimed 32 lives, most of them migrant farm workers being deported to Mexico. Guthrie had been stung into action by contemporary radio and newspaper reports of the tragedy, which often neglected to mention the names of those killed, referring to them only as deportees. The song’s central thrust – a call for dignity and respect for those painted as ‘inferior’ – echoes the sentiment of Committed To Parkview.

Lamenting America’s Past
If there’s an overriding theme to Highwayman, it’s one of reflection. Songs like Ed Bruce’s The Last Cowboy Song, Cindy Walker’s Jim, I Wore A Tie Today and the Steve Goodman/John Prine co-write, The Twentieth Century Is Almost Over, lament the loss of a pioneering American past where myths and heroes thrived in equal measure. “Pannin’ for gold on the cuff/ We did everything in the books, I guess/ And a lot that they never thought of,” Cash and Nelson harmonise on the requiem for a departed friend that is Jim, I Wore A Tie Today. They could easily be singing about themselves.

Elsewhere, on Bob Seger’s Against The Wind, Nelson gets wistful about the surety of times gone by, seeking shelter from a present loaded with uncertainties: “The years rolled slowly past/ I found myself alone/ Surrounded by strangers I thought were my friends/ I found myself further and further from my home.”

The foursome truly excel on Guy Clark’s Desperados Waiting For A Train. A hymn to the peculiar bonds of friendship in the face of advancing years, its characters like players in “some old western movie”, it could’ve been written for The Highwaymen.

Their respective voices move through the song with an air of resignation that sounds both weary and contented, as if there’s not much more to be done. The implication being that the protagonists’ best days are behind them. In each of their cases – but particularly when it came to Cash, still nearly a decade away from the start of his association with Rick Rubin – this proved to be plainly untrue.

Released in 1985, the album – credited to Waylon Jennings, Willie Nelson, Johnny Cash, Kris Kristofferson as opposed to The Highwaymen – was an artistic and commercial hit. It made the top spot on the US Country charts and went platinum, propelled by the iconic title track, which came with an evocative black-and-white video. The tune also earned Jimmy Webb a Grammy for Best Country Song.

It was the beginning of a decade-long run that yielded two more studio albums and a succession of lucrative tours, a situation that far exceeded Cash’s original vision.
“The Highwaymen turned out to be much more than a one-shot deal,” Nelson wrote in My Life. “We saw it as one non-stop transcontinental party. Our wives, our kids, our friends – everyone got along. In spite of the size of the entourage, we travelled the world as one big happy family. I don’t mean that we didn’t get a little cranky from time to time. Hell, we were getting up there in age. Old pickers tend to get a little cranky. For the most part, though, it was smooth sailing.”

Only the onset of ill health, regarding Jennings and Cash, brought things to a close in the late-90s. They died within a short space of one another – in 2002 [Jennings] and 2003 [Cash] respectively.

When I interviewed Kristofferson in 2004, he was still mourning the absence of his old friends. “When we all got together as The Highwaymen, it was incredible,” he said. “I loved it, but I wish now that I’d realised how short it was going to be. It’s like life in that respect. It was such a blessing because every guy up there was my hero. And standing up on stage with them, all singing together and acting like equals, was pretty heady stuff. Now Willie and I are the only ones left. I wish I’d appreciated it more.”



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