About the song
Released in 1985 as the title track of their debut album, “Highwayman” brought together four legends—Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson—creating a synergy that was, quite frankly, magical. The song itself, brilliantly penned by Jimmy Webb, tells the story of a single soul reincarnated across different eras and forms: first, a highwayman in the 18th century; then, a sailor on a clipper ship; next, a dam builder in the American West; and finally, an astronaut. Each verse is sung by a different member of The Highwaymen, perfectly matching the character’s voice to the singer’s distinctive timbre and persona. This unique structure allows the narrative to unfold with both grand scope and intimate detail.
What makes “Highwayman” so incredibly captivating is the genius of its concept and the flawless execution by these four titans. Each artist embodies their particular character with such conviction: Willie Nelson’s weary, world-wise tone for the highwayman; Kris Kristofferson’s thoughtful, slightly melancholic delivery for the sailor; Waylon Jennings’s raw, powerful grit for the dam builder; and Johnny Cash’s stoic, authoritative voice for the astronaut. Their individual performances are stellar, but it’s the collective power, the shared understanding of life’s fleeting nature and the persistence of the soul, that truly elevates this song. For listeners who have accumulated decades of experience and reflection, the theme of continuous journey, of a spirit moving through different lives and contributing to history, strikes a particularly deep chord. It speaks to the idea that some essence of us endures, witnessing the vast tapestry of existence.
Musically, the production of “Highwayman” is fittingly understated, allowing the narrative and the voices to remain the absolute focus. The acoustic guitar work is precise, the rhythm section provides a steady, almost marching pulse, and subtle atmospheric touches contribute to the feeling of a grand, unfolding story. It builds slowly, drawing you into its lyrical world, proving that true power lies not in bombast, but in profound storytelling and authentic delivery. “Highwayman” isn’t just a classic country song; it’s a philosophical folk epic, a timeless reflection on life, death, and reincarnation, brought to breathtaking life by The Highwaymen. It’s a testament to the enduring power of music to explore the biggest questions, reminding us that some journeys truly have no end.
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
