An affectionate eulogy for an aging hero, told through the lens of a Texas childhood.
The version of “Desperados Waiting for a Train” featuring Nanci Griffith and the song’s legendary writer, Guy Clark, is a poignant, all-star tribute, released on Griffith’s 1998 album, Other Voices Too (A Trip Back to Bountiful). This particular recording did not chart as a single in its own right, as it was a deeply personal cover on an album dedicated to classic folk and country songs, but the composition itself had already cemented its place in country music history. The most famous charting version was by the country supergroup, The Highwaymen (composed of Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson), who took their rendition to No. 15 on the Billboard Hot Country Singles & Tracks chart in 1985. The brilliance of Griffith’s take, however, is the presence of Guy Clark himself, surrounded by a veritable who’s who of Texas singer-songwriters—including Jerry Jeff Walker, Steve Earle, and Rodney Crowell—turning the track into a warm, heartfelt reunion and a defining moment of Americana music.
The story behind this profoundly moving song is one of real-life affection and bittersweet memory. Guy Clark wrote “Desperados Waiting for a Train” as a “eulogy,” an ode to a beloved man named Jack Prigg, who was the long-time boyfriend of Clark’s paternal grandmother. While Clark’s father was away serving in World War II, Prigg became the crucial male figure in his young life. He was an oil driller and a true “old school man of the world”—a drifter who taught the young Clark how to drive and took him to places like the Green Frog Cafe where old men would “lie ’bout their lives while they’d played” dominoes. This old man, with his life etched in seventy years of living, came to represent a kind of mythical, wandering hero to Clark.
The heart of the song’s meaning lies in this dual perspective: the romanticized view of childhood companionship contrasted with the harsh reality of aging and decline. The title’s powerful metaphor—“desperados waiting for a train”—evokes the shared, transient quality of their lives, like characters in an old Western movie, always on the move or waiting for the next ride. It is a striking image that captures the essential restlessness of the American spirit, though in the end, the “train” they await is not a fresh start, but the final, inevitable journey. Clark’s lyrics are deceptively simple, yet packed with emotional weight, particularly when the narrator describes his older friend crying while listening to “Red River Valley,” wondering if “ever’ well I’ve drilled gone dry.” It’s a universal moment of existential reckoning, the sudden awareness of one’s own mortality and legacy.
For those of us who grew up knowing the ache of lost time and the irreplaceable bond with an older mentor, the Nanci Griffith and Guy Clark version acts like a photograph pulled from a dusty attic. Griffith’s clear, empathetic voice provides the narrative clarity, but it is Clark’s gravel-laced counter-vocal—the voice of the man who lived the story—that lends it an almost sacred authenticity. Listening to it now, decades later, you don’t just hear a song; you feel the Texas dust, smell the cheap coffee, and remember the quiet wisdom of the old souls who shaped your own forgotten childhoods. It’s a moment of reflection that reminds us that, in the end, we’re all just desperados, waiting our turn.