THE LAST OUTLAW AT THE EDGE OF THE HORIZON: Willie Nelson — “Highwayman”
On September 28, 2024, the world dimmed just a little as the news spread: Kris Kristofferson, the Rhodes Scholar poet who reshaped the heart of Nashville, had passed away at eighty-eight. With his departure, a heavy and historic mantle fell upon the shoulders of Willie Nelson. Suddenly, the “Red Headed Stranger” stood as the final living member of The Highwaymen, the Mount Rushmore of country music that once featured Johnny Cash, Waylon Jennings, and Kristofferson. When they first gathered in 1985 to record their debut album, they weren’t just a supergroup; they were a brotherhood of outlaws who had survived the Nashville machine, addiction, and the changing tides of time, coming together to prove that the spirit of rebellion was immortal.
Background
The title track, “Highwayman,” written by Jimmy Webb, became the haunting manifesto of this quartet. Each verse allowed one of these titans to tell the story of a soul that refuses to die—a bandit, a sailor, a dam builder, and a pilot of a starship. Listening to it now, the song feels less like a folk tale and more like a prophecy. There is a profound, aching weight in hearing Willie’s voice today, knowing that the “around and around” he sings of is a journey he now navigates as the sole guardian of their shared memory. It is a meditation on the cyclical nature of life and the stubborn persistence of the human spirit.
Introduction
There is a deep, quiet sadness in seeing the campfire of the Outlaw era burn down to its final, flickering ember. For decades, these four men represented a brand of rugged truth that couldn’t be manufactured in a corporate office. They sang for the broken, the wandering, and the defiant. Now, as Willie continues to tour and record into his nineties, he carries not just his own legacy, but the ghosts of his three brothers. Every time he strikes a chord on his battered guitar, “Trigger,” he is playing for Johnny’s gravity, Waylon’s drive, and Kris’s poetic soul.
As the final, shimmering notes of the pedal steel guitar drift into the stillness of the night, we are left with a sense of immense gratitude. The Highwaymen taught us that while the flesh may fail and the road may end, the stories we tell and the songs we leave behind possess a life of their own. The highway goes on forever, and though the lineup has changed, the spirit of the ride remains unbroken.
Video
Lyrics
🎵 Let’s sing along with the 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