Desperados Waiting for a Train is also one of the songs that members of the Western Writers of America chose as one of the Top 100 Western songs of all time. Guy Clark wrote the song while Jerry Jeff Walker originally recorded it for his 1973 album Viva Terlingua. American country music supergroup the Highwayman – composed of four of country music’s biggest: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson – released it in September 1985 as the second single from the album Highwayman. The group’s version reached #15 on the Billboard Hot Country Singles & Tracks chart.

About the Song

The song tells the story of a boy who admires and looks up at an old man. However, as the little boy watched the man get older, he found him becoming more like every other older man he knew.

Throughout the song, he compared himself and the man to those desperados waiting for a train – something that may seem thrilling and risky, but in the end, it’s pretty unexciting. According to Clark, the song was inspired by his grandmother’s longtime boyfriend named Jack, who became a grandfather figure to him. He penned the song when Jack died.

Moreover, all of the things in the song happened in real life, and it’s as accurate as Clark remembers it, almost word for word. He said that it’s a real song about someone in his life.

Desperados Waiting for a Train Popular Recordings

A lot of artists have covered Desperados Waiting for a Train. Some of the most popular versions were recorded by:

• Guy Clark
• Jerry Jeff Walker
• Rita Coolidge
• David Allan Coe
• Tom Rush
• Slim Pickens
• The Highwaymen
• Nanci Griffith
• Steve Earle
• Rodney Crowell
• Jimmie Dale Gilmore
• Eric Taylor
• Jason Isbell

In Albums

The song has been released in the tracklist of many albums including:

• Viva Terlingua
• Fall into Spring
• The Mysterious Rhinestone Cowboy
• Ladies Love Outlaws
• Highwayman
• Other Voices Too (A Trip Back to Bountiful)
• Old No.1

Listen (Guy Clark Version)

Desperados Waiting for a Train Lyrics

I'd play the Red River Valley
And he'd sit out in the kitchen and cry
And run his fingers through seventy years of livin'
Wonder, "Lord, has ever' well I've drilled run dry?"

We were friends, me and this old man
Like desperados waitin' for a train
Like desperados waitin' for a train

He's a drifter and a driller of oil wells
And an old school man of the world
He 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 were like some old western movie
Like desperados waitin' for a train
Like desperados waitin' for a train

From the time that I could walk he'd take me with him
To a bar called the Green Frog Cafe
There was old men with beer guts and dominos
Lying 'bout their lives while they'd played

And I was just a kid
They all called his "Sidekick"
It's like desperados waitin' for a train
It's like desperados waitin' for a train

One day I looked up and he's pushin' eighty
And there's brown tobacco stains all down his chin
Well to me he's one of the heroes of this country
So why's he all dressed up like them old men?

Drinkin' beer and playin' Moon and Forty-two
It's like desperados waitin' for a train
Like desperados waitin' for a train

A day before he died, I went to see him
And I was grown and he was almost gone
So we just closed our eyes and dreamed us up a kitchen
And sang another verse to that old song
"Come on, Jack, that son of a guns are comin'"

We're desperados waitin' for a train
Like desperados waitin' for a train
We're like desperados waitin' for a train
Like desperados waitin' for a train