Based on the 1970s film of the same name, "The Comeback Trail" follows Max Barber (Robert De Niro), a man in debt to a mob boss (played by Morgan Freeman), who creates an insurance fraud by casting washed-up, suicidal cowboy/movie star Duke Montana (Tommy Lee Jones) in a poorly written Western with the intention of killing him during the first days of filming. Duke somehow rises to the occasion, redeems his past misdeeds and brings Max and others along on the same journey.