When I’m in the mood to hear a well-written song, I go to either John Prine, Townes Van Zandt, Bob Dylan, Steve Earle, or Guy Clark. They always hit the spot, and this song is one of those story songs that just stuck with me. I look at some of these songwriters not as normal songwriters but mini movie writers.
Guy Clark wrote this song in the early ’70s, drawing from his own childhood in Texas. The old drifter in the song, the surrogate grandfather who taught him about cards, women, and hard living, wasn’t made up. Jack Prigg, a wildcatter and oilfield worker, had lived in Clark’s grandmother’s boarding house, and a young Guy Clark soaked up every curse word and story. By the time Clark wrote the song, the memories meant something more universal, a man who refused to fade quietly.
The song was on Clark’s 1975 album, Old No. 1, and it quickly became one of his signature songs. But it didn’t stop there; it was picked up and recorded by Jerry Jeff Walker (first recording of the song), Tom Rush, Rita Coolidge, and, eventually, The Highwaymen (Waylon, Willie, Kris, and Johnny), covering it in 1985. It’s been covered 32 times. Walker, Coolidge, David Allan Coe, and Tom Rush covered it before Guy released his version.
This is wonderful Americana storytelling is as rich as anything you have heard or watched. He writes these story songs so well that you can see them in your head being acted out like a movie.

Jack Prigg was an old oil wildcatter and oilfield worker who lived for a time in Clark’s grandmother’s boarding house in Monahans, Texas, during the 1940s. Clark’s parents had split up when he was young, and he spent a big part of his boyhood around his grandmother’s place. That’s where he met Prigg, who was already an old man by then, tough and weathered from a lifetime in the oilfields. Clark mentioned that he didn’t romanticize the lyrics, he wrote them straight. That’s why this song works, everything is left intact. Clark said, “He was my hero. He was a tough old bird who drank hard, swore a lot, and lived a big life.”
Desperados Waiting For The Train
I’d play the Red River ValleyAnd he’d sit in the kitchen and cryAnd run his fingers through 70 years of livin’And wonder, “Lord, has ever, well, I’ve drilled gone dry?”We was friends, me and this old man
We was like desperados waiting for a trainLike desperados waiting for a train
Well, he’s a drifter and a driller of oil wellsAnd an old-school man of the worldHe taught me how to drive his carWhen he’s too drunk toAnd he’d wink and give me money for the girlsAnd our lives was like some old western movie
Like desperados waiting for a trainLike desperados waiting for a train
From the time that I could walk, he’d take me with himTo a bar called the Green Frog CafeAnd there was old men with beer guts and dominoesLying ’bout their lives while they playedAnd I was just a kid that they all called his sidekick
We was like desperados waiting for a trainLike desperados waiting for a train
One day I looked up and he’s pushin’ 80And there’s brown tobacco stains all down his chinWell, to me he’s one of the heroes of this countrySo why’s he all dressed up like them old men?Drinkin’ beer and playin’ Moon and 42
Just like a desperado waiting for a trainLike a desperado waiting for a train
And then the day before he died, I went to see himI was grown and he was almost goneSo we just closed our eyes and dreamed us up a kitchenAnd sang another verse to that old song“Come on, Jack, that son of a bitch is coming”
And we’re desperados waiting for a trainLike desperados waiting for a trainLike desperados waiting for a trainLike desperados waiting for a train
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