Released in 1985, “Highwayman” is a single from the Highwaymen, a country supergroup made up of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Written by Jimmy Webb, “Highwayman” is built around the idea of one soul living multiple lives across time. Each verse takes on a new identity, from an outlaw to a sailor to a laborer and finally a space traveler.
Below is an interpretation of the lyrics in “Highwayman,” breaking down each part of the story.
- Song: Highwayman
- Artist: The Highwaymen
- Songwriter: Jimmy Webb
- Released: 1985
- Album: Highwayman
- Genre: Country
What is “Highwayman” About?
Verse 1: Outlaw Life and Violent Ends
I was a highwayman
Along the coach roads I did ride
A highwayman was a robber who traveled on horseback and attacked people along roads, especially in the 18th and 19th centuries.
In this first life, he’s living fast and dangerously, roaming from place to place looking for his next target.
With sword and pistol by my side
Many a young maid lost her baubles to my trade
He’s armed and ready for violence, using fear and weapons to steal.
“Baubles” refers to jewelry or valuables.
He isn’t just robbing the rich or powerful. He’s taking whatever he can, even from innocent women.
Many a soldier shed his lifeblood on my blade
The bastards hung me in the spring of ’25
He killed people, including soldiers, during these robberies. But his actions caught up to him.
He was executed in 1825 by hanging, which was a common punishment for highwaymen at the time.
But I am still alive
Even though his body was killed, he claims he lives on.
This starts the song’s recurring idea: death doesn’t end everything. The soul keeps moving.
Verse 2: A Life at Sea
I was a sailor
I was born upon the tide
In this life, he’s a sailor, someone who’s lived on the ocean since birth.
It’s a full shift from life on land to life on the water.
And with the sea I did abide
I sailed a schooner around the Horn to Mexico
Sailing a schooner around Cape Horn, one of the most dangerous sea routes in the world, shows both skill and courage.
He’s taking on serious risks in this life, too.
I went aloft and furled the mainsail in a blow
And when the yards broke off they said that I got killed
Climbing the ship’s rigging during a storm, he tried to pull in the sail, but the mast snapped. He fell or was crushed.
People assumed he died during the accident.
But I am living still
Again, the body dies, but something essential survives.
The idea of a soul continuing through different lifetimes repeats, showing how he can’t be fully destroyed.
Verse 3: Labor and Sacrifice
I was a dam builder
Across a river deep and wide
He’s now a worker helping build a dam.
This is a life defined by effort and labor, not crime or adventure. It’s a life about contribution and creation.
Where steel and water did collide
A place called Boulder, on the wild Colorado
This refers to the Hoover Dam (originally called Boulder Dam), built during the Great Depression.
It’s a massive structure where human force meets natural power
I slipped and fell into the wet concrete below
They buried me in that gray tomb that knows no sound
He died on the job, falling into the dam’s concrete as it set.
This isn’t just a metaphor. There are stories about workers being trapped in the structure.
His grave is silent, cold, and buried inside the dam itself.
But I am still around
I’ll always be around and around…
Even in the most permanent-seeming grave, he says he’s still here.
The repeated “around and around” pushes the idea of a cycle. This soul keeps coming back, no matter what.
Verse 4: A Future Beyond Earth
I fly a starship
Across the Universe divide
Now he’s no longer bound to Earth. He’s become a being who travels through space, moving past human limits.
It’s the most extreme jump yet, taking him out of history and into the future or something beyond time.
And when I reach the other side
I’ll find a place to rest my spirit if I can
He’s still searching, even across galaxies, for peace. Death hasn’t brought it. Rebirth hasn’t brought it.
He’s looking for rest, but it’s unclear if that’s even possible.
Perhaps I may become a highwayman again
Or I may simply be a single drop of rain
He could return to Earth in the same form as before, or as something entirely different, like a single drop of rain.
There’s no limit to how or where the soul could appear.
But I will remain
And I’ll be back again and again…
No matter what happens or how many times he dies, he insists on returning.
That’s the heart of the song: a constant presence that outlives every ending.
“Highwayman” Song Meaning: A Soul That Refuses to Disappear
“Highwayman” is about reincarnation, but not in a soft, abstract way. Each verse shows a different life with its own risks, violence, and tragedy. Whether robbing stagecoaches, braving storms, building monuments, or flying through space, there’s always danger, and always death. But what ties it all together is the soul that keeps showing up in new forms, refusing to disappear.
There’s also something very human here. It’s not just about one soul across time, but about the feeling that something inside us doesn’t die when the body does. The song hints at spiritual survival, maybe even cosmic energy. Some listeners might see it as religious, others as poetic, but either way, it’s grounded in the idea that death is never the final word.
Songs Like “Highwayman”
If you’re a fan of “Highwayman,” here are some other songs with similar themes of death, rebirth, identity, and something beyond this life:
1. “If I Had a Boat” by Lyle Lovett
“If I Had a Boat” uses dreamlike ideas and shifting metaphors to talk about freedom and escape from ordinary life. It mixes playfulness with loneliness, imagining different ways a person might leave everything behind.
2. “The Pilgrim: Chapter 33” by Kris Kristofferson
“The Pilgrim: Chapter 33” is about a man who’s been broken down, picked apart, and misunderstood. It’s someone who keeps going even when nothing makes sense.
3. “Pancho & Lefty” by Townes Van Zandt
“Pancho & Lefty” tells the story of two outlaws, one who dies and another who betrays. It’s full of questions about fate, guilt, and what happens after the violence fades.
4. “The Weight” by The Band
“The Weight” is full of mysterious characters and strange encounters, all linked by a feeling of burden and constant movement. It feels like a journey that never really ends.
Related: “The Weight” Song Meaning
Conclusion: Life After Death, Again and Again
“Highwayman” paints four different lives and four different deaths, but the same soul keeps returning. Whether it’s through violence, accident, or exploration, something essential keeps moving forward.
It’s a song about survival beyond reason. It’s a kind of persistence that can’t be buried, drowned, crushed, or even lost somewhere out in the universe.
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