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Introduction
There’s something undeniably magnetic about “Highwayman”. It’s not just a song—it’s a journey through time, a narrative that weaves together four distinct lives, each voiced by one of country music’s greatest legends. When you listen to it, it’s like hearing the spirit of adventure itself speaking through Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Each verse tells a different story, but they’re all bound together by a common thread: resilience and a defiant embrace of fate.
The song opens with Willie Nelson’s unmistakable voice embodying a 19th-century highwayman—a bold and audacious outlaw who lived by his own rules, riding fast and free. His tale feels like a whisper from the past, as vivid as an old western painting come to life. But the highwayman’s story ends abruptly, and the music shifts, seamlessly transporting us to another time and another place.
In the second verse, Waylon Jennings steps in as a sailor. His life is a world away from the dusty roads of the first verse, and yet, there’s a similar sense of daring. He braves the high seas, facing dangers that would scare lesser men. Listening to Waylon’s deep, steady voice, you can almost feel the salty breeze and the sway of the ship beneath your feet. But, just like the highwayman, his story, too, ends in tragedy—swept away in the unforgiving waves.
Kris Kristofferson’s verse takes us to the early days of modern industry. His character, a dam builder, is no less fearless than the others. With lines that capture both the pride and the peril of his work, he’s a man who shapes the landscape itself. Yet, the danger that follows the Highwayman and the Sailor is still there—this time, in the form of a tragic fall. And then, the verse fades, leaving a poignant silence in its wake.
Finally, Johnny Cash’s voice emerges like a force of nature. He’s a starship pilot, a man who’s left the Earth altogether. His verse is laced with a sense of timelessness and immortality. Through him, the song becomes something greater than just a tale of past lives—it’s a meditation on the eternal human spirit, on how we keep coming back, time and again, driven by the same passions and fears, no matter where—or when—we find ourselves.
“Highwayman” is haunting, hopeful, and humbling. Each verse, each character, is distinct, yet they all belong to the same soul—a soul that cannot be broken or erased, even by death. It’s this unbreakable spirit that has made the song a classic, one that resonates deeply with anyone who’s ever faced loss, change, or the relentless march of time. In the hands of The Highwaymen, it’s more than a song—it’s a legend.
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 twenty-five
But I am still alive
I was a sailor
I was borne 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 and around
I 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
I’ll be back again and again and again and again and again and again