About the song
Good day, everyone. It’s a real pleasure to talk about a song that is more than just a collaboration; it’s a summit of legends, a moment in music history that brought together four of the most iconic and rebellious voices to ever grace the stage. I’m speaking, of course, about the supergroup The Highwaymen, and their haunting and timeless anthem, “Highwayman.”
When Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson joined forces in 1985, it was a seismic event in country music. These four men, the very architects of the “outlaw” movement, were no longer young rebels, but seasoned veterans with a combined legacy that was unparalleled. They chose to name their group after this particular song, and for good reason. Written by the masterful Jimmy Webb, “Highwayman” is a cinematic masterpiece, a profound story of reincarnation that perfectly captures the restless, rebellious spirit that defined each of their careers.
The genius of the song is in its structure. It’s a four-verse narrative, with each of the four men taking a turn to tell the story of a soul that lives on through different lifetimes. Willie Nelson, with his smooth and weary voice, begins as the highwayman, a horseman who “rode a horse, and I killed a man.” He’s a figure of romanticized rebellion, but one who ultimately meets a violent end. Kris Kristofferson, with his gruff, poetic delivery, then embodies a sailor who “sailed the sea of a thousand years,” a man who lives a life of adventure but is ultimately swallowed by the waves. Waylon Jennings, his voice a powerful and defiant rumble, becomes a dam builder who “died in my sleep” but whose work still stands. And finally, Johnny Cash, with that deep, prophetic baritone, takes us to the stars as a starship pilot, a man who will “fly a starship across the universe divide.”
The song’s final chorus, when all four of their voices join together, is a moment of pure magic. It’s a powerful and moving harmony that symbolizes the shared journey of the soul and the interconnectedness of all their stories. It’s not just a beautiful melody; it’s a testament to the idea that the outlaw spirit—the desire for freedom and the refusal to be bound by convention—is a timeless force that lives on forever.
“Highwayman” wasn’t just a hit song; it was the definitive statement for this supergroup. It proved that these aging legends were still as vital and relevant as ever, and that their combined talent was a force of nature. It’s a song that speaks to a bigger truth about life, death, and the enduring power of a human spirit that can never be truly killed, only reborn. It remains a high watermark for country music and a powerful tribute to four irreplaceable icons.
Video
Lyrics
I was a highwayman
Along the coach roads I did ride
With sword and pistol by my side
Many a young maid lost her baubles to my trade
Many a soldier shed his lifeblood on my blade
The bastards hung me in the spring of 25
But I am still alive
I was a sailor
I was born upon the tide
And with the sea I did abide
I sailed a schooner round the Horn to Mexico
I went aloft and furled the mainsail in a blow
And when the yards broke off they said that I got killed
But I am living still
I was a dam builder
Across the river deep and wide
Where steel and water did collide
A place called Boulder on the wild Colorado
I slipped and fell into the wet concrete below
They buried me in that great tomb that knows no sound
But I am still around
I’ll always be around, and around and around and around and around
I’ll fly a starship
Across the Universe divide
And when I reach the other side
I’ll find a place to rest my spirit if I can
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 and again and again and again and again
