“Highwayman” isn’t just a song; it’s a full-blooded journey through lives and eras, the kind that grabs you by the soul and takes you on a ride through history. Sung by the unforgettable quartet of Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings—better known as The Highwaymen—this song tells four gripping stories, each with its own life and death, all anchored in the shared spirit of adventure and resilience.
Each verse feels like a chapter in a larger-than-life novel, with each singer embodying a different character who meets their fate but somehow carries on. Willie’s haunting portrayal of a reckless highwayman, Waylon’s steadfast sailor lost at sea, Kris’s brave worker on a damned dam, and Johnny’s astronaut venturing into the unknown—these characters aren’t just symbols. They’re people you could imagine meeting across different times and places, all driven by a kind of timeless grit. There’s an unbreakable spirit in each voice, a reminder that life’s essence endures, no matter the path or peril.
What makes “Highwayman” truly special, though, isn’t just the iconic voices or the powerful storytelling; it’s that deep sense of immortality, that feeling of “I’ll be back again.” There’s something soul-stirring about hearing these legends sing not just of life and death, but of continuation, rebirth, and purpose. The song taps into that unspoken understanding that even as we move through life’s trials, part of us remains—echoing, living on, leaving a legacy.
Every time you listen to “Highwayman,” it’s like catching up with an old friend who’s come back from some far-off journey, with tales that’ll make your heart ache and soar at once. It’s a song that resonates on a level most can’t touch, timeless and forever relevant. And maybe that’s what makes it so unforgettable: the feeling that, no matter where we go or what we face, the essence of who we are will live on, just like the Highwaymen
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