About the song
“Highwayman” by The Highwaymen. Penned by the brilliant songwriter Jimmy Webb in 1977, this extraordinary tale of reincarnation and perpetual motion found its perfect interpreters when it became the title track and defining anthem of the supergroup’s 1985 debut album. Featuring the combined, colossal talents of Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson, this song wasn’t just a number one hit; it was a powerful statement of identity, instantly cementing the group’s iconic status and weaving a narrative as grand as the landscapes these men had traversed.
The lyrics of “Highwayman” are a true lyrical masterpiece, crafting a unique narrative where a single soul lives through four distinct, archetypal lives across different historical periods. Each verse introduces a new incarnation: first, a highwayman (a defiant robber who dies by the sword); then, a sailor caught in a storm (“born on the wave and died on the foam”); next, a dam builder who perishes in his grand construction; and finally, a starship commander soaring through the cosmos. The common thread is a restless spirit, an unwavering quest for freedom, and a defiant embrace of destiny. Phrases like “I was a highwayman” and “I’ll be back again, and again, and again, and again” beautifully convey the song’s central theme of reincarnation and the human spirit’s undying drive to explore, to challenge, and to exist outside the bounds. It speaks to a deep sense of purpose, a refusal to be constrained by a single lifetime, and the notion that some souls are simply meant to keep riding, no matter the form.
The Highwaymen’s vocal performance on “Highwayman” is what elevates it from a great song to an absolute legend. Each of the four titans takes a dedicated verse, their individual voices perfectly embodying the character and era of their respective “highwayman.” Johnny Cash’s deep, resonant baritone lends a chilling gravitas to the doomed outlaw; Willie Nelson’s signature mellow, contemplative phrasing brings a weary wisdom to the seafaring man; Waylon Jennings’s assertive, no-nonsense delivery captures the rugged determination of the dam builder; and Kris Kristofferson’s gravelly tone gives an almost cosmic perspective to the starship commander. Their combined gravitas, their lived experience, and their distinct personalities weave a powerful, unforgettable tapestry, making the narrative feel both epic and deeply personal. It’s a masterclass in collaborative storytelling, each legend contributing a vital thread to the grand design.
The musical arrangement of “Highwayman” is atmospheric, folk-country, and perfectly suited to the song’s sweeping narrative. It features a driving yet contemplative acoustic guitar rhythm that provides a consistent, almost hypnotic pulse, suggesting the relentless passage of time and lives. Subtle orchestration, including a gentle fiddle and ethereal synths (especially in the space-faring verse), adds layers of texture and emotion without ever overwhelming the core instrumentation or the powerful vocals. The production is clean and expansive, allowing the intricate lyrical journey and the distinct voices of each artist to take center stage.
“Highwayman” resonated deeply with audiences worldwide, becoming an instant classic and a defining anthem for The Highwaymen. Its unique blend of storytelling, philosophy, and the sheer star power of its performers earned it a Grammy Award for Best Country Vocal Performance by a Duo or Group. It remains one of country music’s most unique and powerful songs, a timeless ode to destiny, defiance, and the enduring quest of the human spirit that will undoubtedly be back again, and again, and again.
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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…
