About the song
When exploring the vast tapestry of American music, few collaborations stand as tall—both in legend and in sound—as **The Highwaymen**. Comprised of four of country music’s most iconic voices—**Johnny Cash**, **Willie Nelson**, **Waylon Jennings**, and **Kris Kristofferson**—this supergroup brought together not only individual greatness but also a shared reverence for storytelling, grit, and the American spirit. Their 1985 debut single, **“Highwayman,”** does more than simply introduce a band; it offers a mythic meditation on identity, mortality, and the enduring soul.
Originally penned by **Jimmy Webb**, **“Highwayman”** is a sweeping, poetic ballad that travels across time and space, told through the reincarnated memories of a soul inhabiting different lives: a highwayman, a sailor, a dam builder, and a starship pilot. Each verse is sung by a different member of **The Highwaymen**, whose distinct vocal textures bring an almost sacred weight to their respective characters. **Nelson**’s nasal warmth sets the tone with the reckless yet romantic highwayman. **Jennings** follows as the mariner, somber and defiant. **Kristofferson** delivers the dam builder’s tale with a worn, earthy sorrow, and finally, **Cash**’s deep baritone takes us into the cosmos—a voice that feels eternal in itself.
The song’s structure and concept are as audacious as they are moving. At heart, **“Highwayman”** is about resilience and transcendence—the idea that a spirit can’t be pinned down by death, that the human drive to explore, build, and defy limits is a kind of immortality. It’s a fitting anthem not just for the characters within the song, but for the artists singing it. Each member of **The Highwaymen** had already lived the lives of outlaws, poets, and wanderers; this song simply gave them mythic masks to wear.
Musically, the track balances traditional country instrumentation with atmospheric flourishes—synths and reverb that elevate its final frontier vision. The production never overwhelms the vocals; rather, it amplifies the quiet grandeur of the lyrics. And in doing so, **“Highwayman”** becomes more than a country song. It becomes a fable—one told by four men who had seen more than most, and still had stories left to sing.
For older listeners, especially, this song resonates deeply. It reminds us that life is a journey not of one form, but of many. We build, we lose, we move on. And if we’re lucky, as **The Highwaymen** suggest, we live on—not just in memory, but in the songs we leave behind.
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 life blood 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 to furl 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 gray 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’ll fly a star ship 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
