About the song
Desperados Waiting for a Train by The Highwaymen is more than just a song—it’s a heartfelt tribute to friendship, memory, and the unyielding passage of time. Performed by the legendary supergroup The Highwaymen, which brought together four of country music’s most iconic voices—Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson—this song captures the rugged soul of Americana storytelling.
Originally written by Guy Clark in 1973, the song found new life in the hands of The Highwaymen on their 1985 debut album. It’s a raw and poignant ballad that pays homage to the relationship between a young man and an old drifter who becomes both a mentor and a surrogate grandfather. The lyrics weave together vivid snapshots of shared experiences, capturing the essence of how memories can linger like dust trails behind an old train.
What makes Desperados Waiting for a Train so captivating is how it perfectly balances melancholy with a sense of reverence. The instrumentation is simple but impactful, with the twang of acoustic guitars and the steady rhythm of percussion complementing the gravelly, worn voices of these seasoned legends. Each of the four singers takes a turn with the verses, their distinct styles blending into a powerful, harmonious reflection on aging and loss.
The song’s lyrics carry a weight that resonates deeply—lines like “He was an old school man of the world / With his heart set on a stone” speak to the grit and resilience of those who’ve lived a life of hardship but never lost their spirit. There’s an undeniable tenderness in how the narrator looks back at his time with the old drifter, recalling moments filled with both laughter and bittersweet lessons. It’s storytelling at its finest, delivered with a sincerity that only these four legends could muster.
Listening to Desperados Waiting for a Train feels like sitting around a campfire, hearing tales of a bygone era from voices etched with history. It’s not just a song—it’s a moment of reflection on how people leave their mark on us, even when the world keeps moving forward. The power of this track lies in its authenticity—how it doesn’t shy away from the inevitable truth that time waits for no one. Through every note and every line, the listener is reminded of the beauty and pain that come with remembering those who shaped our lives.
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Lyrics
I played the Red River Valley
And he’d sit out in the kitchen and cry
An’ run his fingers through 70 years of livin’
An’ wonder Lord, as ever, will that drill run dry?
We were friends, me an this old man[All]
Like desperados waiting for a train
Like desperados waiting for a train[Jennings]
He’s a drifter, and a driller of oil wells
And an old-school man of the world
He’d let me drive his car when he’s too drunk to
And he’d wink, and give me money for the girls
And our lives were like some old western movie[All]
Like desperados waiting for a train
Like desperados waiting for a train[Nelson]
From the time that I could walk, he’d take me with him
To a bar, called the Green Frog Cafe
And there were old men, with beer-guts and dominoes
Lying about their lives while they play
And I was just a kid, they called his sidekick[All]
Like desperados waiting for a train
Like desperados waiting for a train[Cash]
One day I looked up, and he’s pushing 80
And there’s brown tobacco stains all down his chin
To me he’s one of the heroes of this country
So why is he all dressed up like them old men?
Drinkin’ beer and playing Moon in 42[All]
Like desperados waiting for a train
Like desperados waiting for a train[Nelson]
The day before he died, I went to see him
I was grown, and he was almost gone
[Cash]
So we just closed our eyes and dreamed of supper kitchens
And sang another verse to that old song
[Jennings spoken]
Come on Jack, that son-of-a-gun’s a-comin’.[All]
Like desperados waiting for a train
Like desperados waiting for a train
Like desperados waiting for a train
Like desperados waiting for a train
