The Story Behind Desperados Waiting for a Train by The Highwaymen

Released in 1985 on their debut album Highwayman, Desperados Waiting for a Train became one of the standout tracks by The Highwaymen—a supergroup composed of country legends Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. The song peaked at No. 15 on the Billboard Hot Country Singles & Tracks chart, bringing Guy Clark’s poignant lyrics to a wider audience.

Written by Clark, the song tells the story of a young boy who admires an older man, only to watch him age and become just another figure of the past. The boy’s perception of the man shifts from hero to someone who has lived a life full of unremarkable moments. The repeated metaphor of “desperados waiting for a train” suggests that while the old men live with a sense of adventure and risk, their lives ultimately become mundane and predictable.

In Clark’s own words, the song was inspired by his grandmother’s longtime boyfriend, Jack, who became a grandfather figure to him. Clark remembered Jack as a “crusty old bachelor who lived life on his own terms,” and wrote the song after Jack’s death. The song was a reflection of their real-life experiences, nearly word for word, capturing the essence of life’s cycle and the transition from youth to old age.

Before The Highwaymen’s version, Desperados Waiting for a Train was recorded by Jerry Jeff Walker in 1973, followed by versions from Rita Coolidge and Tom Rush. However, it was the collaboration of Cash, Nelson, Jennings, and Kristofferson that brought the song into the mainstream, marking a pivotal moment in Clark’s career as a songwriter.

The song became so synonymous with the Highwaymen that Clark was affectionately referred to as the “Fifth Highwayman.” His songwriting legacy, amplified by this track, led to collaborations with artists like Alan Jackson, George Strait, Brad Paisley, and more.

Lyrics

… {Kris
] I’d sing the red river valley
And he’d sit out in the kitchen and cry
And run his fingers through seventy years of living’
Wondering, lord, has every well i drilled ran dry
We were friends, me and that old man
… Like desperados waiting for the train
Like desperados waiting for the train
{Waylon
] He’s a drifter and a driller of oil wells
And an old school man of the world
Taught me how to drive his car when he’s too drunk to
And he’d wink and give me money for the girls
And our lives was like some old western movie
… Like desperados waiting for the train
Like desperados waiting for the train
From the time that i could walk he’d take me with him
To a place called the green frog cafe
And there was old men with beer guts and dominoes
Lying’ about their lives while they played
And i was called his sidekick[willie
… Like desperados waiting for the train
Like desperados waiting for the train
[John
] I looked up and he was pushing eighty
And there was brown tobacco stains all down his chin
To me he’s one of the heroes of this country
So why’s he all dressed up like some old man
Drinking’ beer and playing’ moon in forty-two
… Like desperados waiting for the train
Like desperados waiting for the train
[Willie
] The day before he died i went to see him
I was grown and he was almost gone
So we just closed our eyes and dreamt us up a kitchen
And sang another verse to that old song[john
[Waylon
]”come on, jack, that son of a guns a coming”
… Like desperados waiting for the train
Like desperados waiting for the train
Like desperados waiting for the train

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