Remembering The Highwaymen’s Hit Song “Desperados Waiting For A Train” 

The American country music group the Highwaymen – composed of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson – released “Desperados Waiting For A Train” off their debut album Highwayman in 1985.

The supergroup’s version reached No. 15 on the Billboard Hot Country Singles & Tracks chart.

The Story Behind The Song

Written by Guy Clark, “Desperados Waiting For A Train” tells the tale of a boy who admires and looks up to an old man. However, as the little boy watched the man grow older, he found him becoming just like every other older man he knew. 

All through the song, he compared himself and the man to desperados waiting for a train – something that may seem to be exciting and treacherous, yet in the end, it’s actually pretty dull.

“From the time that I could walk, he’d take me with him to a bar called the Green Frog Café. There were 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.’ Like desperados waitin’ for a train,” the song goes.

Clark revealed that the song was inspired by the longtime boyfriend of his grandmother named Jack, who became a grandfather figure to him. He wrote the song when Jack died, of whom he described to be “a crusty old bachelor who lived life on his own terms.”

Moreover, all the things in the song happened in real life, and it was as accurate as Clark can remember it, nearly word for word. “It’s a true song about someone in my life – I mean, you couldn’t have made that up,” he said. “It’s just as true as you could make it. It was about a guy who was like my grandfather. And when I started writing songs, that was one of the songs I knew I was gonna write at some point.”

Country music singer Jerry Jeff Walker originally recorded the song for his album Viva Terlingua released in 1973. A year later, Rita Coolidge and Tom Rush recorded a version of “Desperados Waiting For A Train” for their albums Fall Into Spring and Ladies Love Outlaws, respectively.

Finally, in 1975, Clark released his version for his debut LP. But the song only became a hit when the Highwaymen recorded it, and it launched Clark’s career as a songwriter. The songs he wrote were then recorded by several country legends such as Kris Kristofferson, Alan Jackson, George Strait, Brad Paisley, Johnny Cash, and Vince Gill, just to name a few.

Clark has also grown quite close to the outlaw country group and was even often referred to as “The Fifth Highwayman.”

Anyway, make sure to watch the Highwaymen’s incredible performance of “Desperados Waiting For A Train” in the video below.