About the song
Willie Nelson’s Red Headed Stranger Medley is more than just a performance—it’s a journey through one of country music’s most haunting and cinematic narratives. Rooted in the legend of the drifting, lonesome cowboy, this medley distills the essence of Nelson’s groundbreaking 1975 concept album, Red Headed Stranger. With its sparse instrumentation and hushed, almost whispered vocals, the album was a revelation at the time of its release, standing in stark contrast to the overproduced, string-laden country music dominating Nashville. It was Willie’s declaration of artistic independence, and it changed the genre forever.
This medley encapsulates the album’s emotional highs and lows, bringing together its most essential moments into a single, seamless experience. At its heart is the titular song, Red Headed Stranger, a ballad of betrayal, revenge, and sorrow, centered on a preacher who kills his unfaithful wife and her lover, only to be left wandering the land, burdened by his sins. This tale of violence and redemption is stitched together with other key pieces from the album, forming a continuous narrative that feels as timeless as an old Western ballad.
What makes this medley particularly compelling is the way Nelson’s voice delivers these stories—not with the fiery bravado of a gunslinger, but with the weary, knowing restraint of a man who has lived with the consequences of his actions. There is an intimacy in his phrasing, an economy of words and notes that allows the weight of the story to settle deep into the listener’s bones. Accompanied by little more than his trusty Martin guitar, Trigger, and a handful of carefully placed instrumental flourishes, Nelson creates a vast emotional landscape with the sparsest of tools.
When Red Headed Stranger was first released, some in the industry feared it was too bare, too quiet to succeed. But that very quality—its starkness, its raw simplicity—was what made it so powerful. It forced listeners to lean in, to fill in the spaces with their own imagination, much like the great folk ballads and cowboy songs of old. The medley format, when performed live or in recorded compilations, only strengthens that effect, making it feel as though Nelson himself is sitting by the fire, spinning the tale for an audience that hangs onto every word.
Beyond its narrative and musical qualities, Red Headed Stranger Medley also serves as a reminder of Nelson’s role as both a storyteller and a rebel. The album defied expectations, and so does the medley—it’s a performance that doesn’t demand attention with flash but instead earns it through quiet command. It’s no surprise that the album, and by extension the medley, became one of Nelson’s most enduring works, inspiring generations of songwriters to embrace the power of restraint and authenticity.
For longtime fans, this medley is a welcome revisiting of a beloved classic, a chance to step back into the world of the Red Headed Stranger and feel its ghosts once more. For new listeners, it’s an invitation—to hear a story that is as old as time, yet as fresh and gripping as the day it was first sung. Willie Nelson doesn’t just sing these songs; he inhabits them. And in doing so, he invites us to do the same.
Video
Lyrics
The red headed stranger from Blue Rock, Montana
Rode into town one day
And under his knees was a ragin’ black stallion
And walkin’ behind was a bay
The red headed stranger had eyes like the thunder
And his lips, they were sad and tight
His little lost love lay asleep on the hillside
And his heart was heavy as night
Don’t cross him, don’t boss him
He’s wild in his sorrow
He’s ridin’ an’ hidin’ his pain
Don’t fight him, don’t spite him
Just wait till tomorrow
Maybe he’ll ride on again
A yellow haired lady leaned out of her window
An’ watched as he passed her way
She drew back in fear at the sight of the stallion
But cast greedy eyes on the bay
But how could she know that this dancin’ bay pony
Meant more to him than life
For this was the horse that his little lost darlin’
Had ridden when she was his wife
Don’t cross him, don’t boss him
He’s wild in his sorrow
He’s ridin’ an’ hidin’ his pain
Don’t fight him, don’t spite him
Just wait till tomorrow
Maybe he’ll ride on again
The yellow haired lady came down to the tavern
An’ looked up the stranger there
He bought her a drink, an’ he gave her some money
He just didn’t seem to care
She followed him out as he saddled his stallion
An’ laughed as she grabbed at the bay
He shot her so quick, they had no time to warn her
She never heard anyone say
Don’t cross him, don’t boss him
He’s wild in his sorrow
He’s ridin’ an’ hidin’ his pain
Don’t fight him, don’t spite him
Just wait till tomorrow
Maybe he’ll ride on again
The yellow haired lady was buried at sunset
The stranger went free, of course
For you can’t hang a man for killin’ a woman
Who’s tryin’ to steal your horse
This is the tale of the red headed stranger
And if he should pass your way
Stay out of the path of the ragin’ black stallion
And don’t lay a hand on the bay
Don’t cross him, don’t boss him
He’s wild in his sorrow
He’s ridin’ an’ hidin’ his pain
Don’t fight him, don’t spite him
Just wait till tomorrow
Maybe he’ll ride on again
