Guy Clark: 12 Essential Songs

From iconic gunfighter anthems to vulnerable proclamations of love

"Desperados Waiting for a Train"

That the Highwaymen — country music's most super-sized supergroup — would release this song as their second single speaks volumes about "Desperadoes Waiting on a Train," which Clark wrote about a Gulf Oil employee who used to rent a room at his grandmother's hotel. The verses read like vignettes, each one shining a light on an unlikely friendship between a boy and an aging, larger-than-life Texan. By the end, the boy is all grown up and the man is dead, having caught a ride on that train bound for somewhere else.