Leadbelly (film) and a drunken friend are playing around with a gun, and Leadbelly accidentally shoots him. He is thrown in prison where he is forced to work in a chain gang. When he tries to escape, he is caught and put in a box. His father arrives and tries to bail Leadbelly out, but fails. Before leaving, he manages to convince the warden to get Leadbelly a twelve-string acoustic guitar. After getting the new guitar, he plays a song for Governor Pat Neff who reassures Leadbelly he will be set free. After he leaves prison, he returns to Fannin Street, sees
When I Was Your Man / And held your hand / Shoulda gave you all my hours / When I had the chance". Its title phrase re-emerges in the final chorus, juxtaposed by Bruno from all the things he "shoulda" done, into things he hopes his ex’s new man will do; concluding: "Do all of the things I should have done / When I was your man". In an interview to "Rolling Stone", Mars revealed, while reluctant, that he wrote the song for his girlfriend, model Jessica Caban, when he was worried about losing her. In contrast with the song, Mars and Caban stayed together;