The Actors (movie, 2003)

During the run of a particularly awful interpretation of Richard III, the star, Anthony O'Malley, begins to frequent a rough pub to develop his character. He meets Barreller who he discovers owes someone he's never met a considerable sum of money. Seeing an opportunity to make some fast money, O'Malley convinces hapless extra, Tom, to meet Barreller as the debt collector.