If you’ve ever wondered what it would sound like if four legends told one story, “Highwayman” is the answer. This song isn’t just a country classic—it’s a journey through time, spirit, and the unbreakable will to keep moving forward, no matter what life throws your way.
“Highwayman” brings together Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson—each a giant in his own right. But when they join forces as The Highwaymen, something magical happens. Each verse is sung from the perspective of a different soul, living and dying across centuries: a highwayman, a sailor, a dam builder, and a starship pilot. It’s like a tapestry of lives woven together by the same thread of resilience and adventure.
What makes this song so special to me is how it captures the idea that our stories never really end—they just change shape. There’s a haunting beauty in the way each Highwayman faces fate with courage, knowing that, in one way or another, he’ll ride again. The harmonies are rich, the lyrics are poetic, and the sense of camaraderie between these legends is palpable. You can feel the weight of their journeys, both in music and in life.
Whenever I hear “Highwayman,” I’m reminded that we’re all part of something bigger—that our struggles, dreams, and even our endings are just chapters in a much grander story. It’s a song for anyone who’s ever felt restless, hopeful, or in search of meaning on the open road.
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Lyrics
[Verse 1: Willie Nelson]
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 ’25
But I am still alive
[Verse 2: Kris Kristofferson]
I was a sailor
I was born upon the tide
And with the sea I did abide
I sailed a schooner around 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
[Verse 3: Waylon Jennings & All]
I was a dam builder
Across a 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, and around…
[Verse 4: Johnny Cash & All]
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
And I’ll be back again
And again, and again, and again
And again, and again…