“Desperados Waiting for a Train" 1973 written by Guy Clark and first recorded by Jerry Jeff Walker, tells a story of a deep friendship between the narrator and an older man. The song uses the metaphor of desperados waiting for a train to represent the passage of time and the anticipation of life's journey. The older man serves as a mentor figure, imparting wisdom and memories. | Kris Kristofferson Fans

“Desperados Waiting for a Train” 2000 by Highwaymen tells the story of a young man’s bond with an older mentor figure—a grandfatherly type who becomes a friend, a teacher, and eventually a reminder of mortality. The narrator recalls moments spent with this man, admiring his wisdom and resilience, even though he’s clearly worn down by age and hardship. Through the lens of their relationship, the song captures the universal truth that time passes relentlessly, and the people we look up to eventual