This was inspired by Townes Vans Zandt's song "Pancho and Lefty," which he recorded for his 1972 album, The Late Great Townes Van Zandt. LaMontagne explained during a Reddit AMA: "I saw Townes in Minnesota when I was about 20-years-old and was just floored by his songs, floored by his performance. As a budding songwriter I was trying to write a song like that."
"Without copying him or imitating him, but trying to capture that essence of a very cinematic story that leaves enough holes within the narrative to engage the imagination of the listener and allow the listener to fill in the blanks," he continued. "I think the best songs are like that. They leave room for your imagination."