“Scroll down to the end of the article to listen to music.”
Introduction
There’s something almost mystical about watching Thomas Gabriel and Whey Jennings perform “Highwayman.” It’s not just that they’re the grandsons of Johnny Cash and Waylon Jennings—though that lineage certainly commands attention. It’s the way their voices seem to channel something deeper than mere genetics, something that speaks to the enduring power of outlaw country’s most iconic supergroup collaboration.
When these two men stand side by side, acoustic guitars in hand at the Rebel Ranch in Ashland City, Tennessee, you can almost feel the ghosts of their grandfathers nodding in approval. Their performance isn’t just a cover—it’s a communion with country music royalty.
The original “Highwayman” was already a song about souls traveling through time, about spirits that never truly die but transform and continue their journey. How fitting, then, that through Thomas and Whey, we witness another kind of reincarnation—the musical DNA of Cash and Jennings finding new expression in their descendants.
Thomas Gabriel carries himself with that same gravitas that made his grandfather the “Man in Black”—his voice has that familiar deep, weathered quality that seems to have lived a thousand lives. Meanwhile, Whey brings that unmistakable Jennings edge—that outlaw grit that defined his grandfather’s revolutionary sound.
What makes their rendition special isn’t just the family connection, though. It’s the reverence with which they approach the material, balanced with their own authentic interpretations. They’re not trying to be carbon copies—they’re honoring a legacy while adding their own chapter to the story.
When they trade verses on this tale of souls moving through time—from highwayman to sailor, dam builder to starship pilot—there’s an almost eerie sense of continuity. The song itself speaks of immortality, and through their performance, Gabriel and Jennings demonstrate how music achieves exactly that—outliving its creators, finding new breath in new voices.
For fans of classic country, watching these two perform feels like witnessing a torch being passed. In an era when traditional country sounds are often sidelined in mainstream music, Thomas Gabriel and Whey Jennings stand as proud custodians of their grandfathers’ rebellious spirit and authentic storytelling.
Their “Highwayman” isn’t just a tribute—it’s a promise that some musical traditions never die. They just find new highways to travel.
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