Introduction
Legends in Harmony: A Journey Through Time with The Highwaymen – Highwayman (American Outlaws: Live at Nassau Coliseum, 1990)
There are moments in music history when time seems to pause — when voices, stories, and melodies transcend the stage and take us somewhere deeper. One such moment unfolds in The Highwaymen – Highwayman (American Outlaws: Live at Nassau Coliseum, 1990), a live performance that doesn’t just entertain, but carries the weight of Americana, the grit of history, and the quiet wisdom of four artists who had long since stopped needing to prove themselves.
The Highwaymen — a supergroup composed of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson — were more than just country legends. They were storytellers, rebels, and poets whose paths, though distinct, converged in a shared belief in authenticity. Their rendition of “Highwayman” during this 1990 performance is nothing short of haunting. Each verse, sung by a different member, unfolds like a chapter in a timeless book — a series of lives lived and lost, told with a weary reverence that only age and experience can lend.
What makes The Highwaymen – Highwayman (American Outlaws: Live at Nassau Coliseum, 1990) so moving is not just the song itself, but how it is delivered. The live setting brings a raw, unvarnished quality to the performance — you can hear the cracks in Cash’s voice, the steady resonance of Nelson’s phrasing, the contemplative tone of Kristofferson, and the weathered soul in Jennings’ delivery. Together, they breathe new life into a song that is, at its core, about rebirth and the eternal nature of the spirit.
This performance isn’t just for fans of country music. It speaks to anyone who has reflected on life’s winding road, its losses, its second chances, and the quiet hope that we carry something forward. Whether you’re revisiting this song after many years or discovering it anew, this version offers a glimpse into a rare musical alchemy — where legends didn’t just sing a song, they became it.
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
[Kris Kristofferson:]
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
[Waylon Jennings:]
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…
[Johnny Cash:]
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…