Four of the toughest men in country music walk into a studio, and what do they sing about? Not drink, not trucks, not women who did them wrong. They sing about a soul that can’t be killed. That’s the odd and rather wonderful business of “Highwayman”, the 1985 hit that gave Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson their group name. People searching for the meaning of the song “Highwayman” often assume it’s a ballad about a bandit on a lonely road. It begins there, but it doesn’t stay put. Written by Jimmy Webb, it’s really about reincarnation, and it asks what becomes of a man after the rope, the wave and the concrete have all done their worst.
Not Really About a Highwayman
Let’s clear something up first. This is not the famous poem by Alfred Noyes about the landlord’s daughter and her doomed lover, nor anything inspired by it, though the title would have you think so. Jimmy Webb’s song borrows the romance of the mounted outlaw only to use it as a doorway. The highwayman of the first verse is simply the first of four lives lived by the same restless spirit, and the song is far more interested in where that spirit goes next than in any coach he ever stopped.
It belongs, if it belongs anywhere, to a small tradition of mystical pop songs about souls and cycles, the sort of thing nobody expected to find on a country radio playlist in the mid-1980s. I find that rather encouraging. It suggests that country music, whatever its reputation, has always had a few strange rooms at the back of the house.
A Dream in an English Hotel
Webb has told the story of its creation more than once. Back in the 1970s he was in England, finishing his album El Mirage with the Beatles’ old producer George Martin, and there was a piano in his hotel suite. One night, after a vivid dream, he stumbled out of bed and over to the piano and began to play, and within a couple of hours he had the first verse.
Then he hit a snag. He didn’t know where the song was going. The answer, he decided, was that the highwayman doesn’t die at all. He is born again, and the next three verses grew out of that single idea, one life after another. Webb recorded it himself in 1977, and very little happened. For years the song sat in a drawer, waiting for the right voices, like an umbrella waiting for rain.
Four Lives, One Soul
Here’s the shape of it. In the first verse our hero is a highwayman, robbing travellers on the old coach roads, and he ends up hanged. In the second he’s a sailor, lost overboard in a storm after a fall from the rigging. In the third he’s a labourer building an enormous dam across the Colorado River, the Hoover Dam by another name, and he slips and is lost in the wet concrete. In the fourth, set in the future, he’s the captain of a starship, crossing the universe and wondering where he might finally rest.
Each of the first three lives ends with a death and then, immediately, a kind of shrug of defiance: whatever has happened, the speaker is still around. It’s gloriously stubborn. There is no wailing here and no self-pity, only a calm insistence that the story isn’t over, which is a very different thing from the usual country song about a man who has lost everything and wants you to know about it.
Why Those Four Lives?
The choice of jobs is neat. A bandit from the age of horses, a sailor from the age of sail, a labourer from the age of steel and concrete, and a captain from an age that hasn’t happened yet: it’s a rough history of human ambition, and every stage of it costs a life. The dam verse has a particular ring of truth, since enormous construction projects have always been paid for, in part, with the bodies of ordinary workers.
The soul that survives each ending isn’t a hero, exactly. He’s more like a witness who keeps being handed a new uniform. The last verse leaves things open, with the traveller free to come back as anything at all, even something small and ordinary. Death, in this song, is less a final whistle than a changing room. You go in as one thing and come out as another, and the match carries on.
How It Found the Right Four Men
Webb’s song lay about for years. Glen Campbell recorded his own version in 1978, which came out in 1979 on an album called Highwayman, but it didn’t take the world by storm either. Then, in 1984, Nelson, Jennings, Cash and Kristofferson were working together on a project with no title, no concept and no group name. Campbell played the song for Cash, and the musician Marty Stuart pointed out that it had four verses, four souls and four of them. It’s the sort of observation that sounds obvious only after somebody has said it.
Each man took one life. Nelson sang the highwayman, Kristofferson the sailor, Jennings the dam builder, and Cash the starship captain, which has the wonderful side effect of giving the deepest voice of the four the last word on eternity. It couldn’t have been better cast if you’d held auditions, and nobody did.
One Song, Four Voices
Listen to the way the verses pass from singer to singer and you can almost hear the lives changing. Nelson’s relaxed, conversational drawl suits a gentleman bandit. Kristofferson’s gravel has salt in it. Jennings brings the swagger of a man who’d happily argue with a concrete mixer. And Cash, last of all, sounds like someone who has seen the far side and come back to report. It’s a bit of theatre, really, four actors in one play, and the song’s whole structure depends on the change of voice.
The Group Takes Its Name
The record came out in 1985 and went to number one on the American country chart. It earned Webb a Grammy for Best Country Song, which must have been satisfying for a man whose song had spent years gathering dust. The four took their name from it, although their first two albums were credited simply to their surnames, and the Highwaymen name wasn’t formally used until the third, in 1995.
There’s a pleasing circularity in that. A song about a soul that keeps returning under different names ended up giving four famous men a shared identity, an outlaw’s badge they could wear together. They’d each been called outlaws for years. Now they had a song that explained why the label never quite fit: outlaws die, but the highwayman, it turns out, just changes his coat.
What It Means
So what does it mean? On the plainest reading, it’s a story about reincarnation: the idea that a spirit travels through many lives, none of which can finally contain it. But I think it’s also a song about stubbornness, about the refusal to be finished. All four singers had been counted out by somebody at one time or another, and here they were, singing about a man who can’t be counted out at all.
It also works as a quiet comfort. Whatever you lose, the song seems to say, something of you carries on. Whether you take that literally or merely as poetry is up to you. I’ve known people who swear by the first reading and people who prefer the second, and the song is generous enough to hold them both.
Conclusion
In the end, the meaning of “Highwayman” is a bit like the song itself: it keeps turning up in new clothes. It’s a ghost story, a history lesson, a piece of science fiction and a gentle argument against the idea that death gets the last word. Four men with plenty of miles behind them gave it voice, and a songwriter who woke in a sweat in an English hotel gave it shape. I’ve heard plenty of songs that wanted to be profound and sounded merely loud. This one only wants to tell you four short stories, and somehow ends up telling you something about forever. Not bad for a record that began with a bandit on a horse.