The Florentine (1999)

The bar in an old Pennsylvania steel town, housed with many of life's losers and disillusioned men, is the main setting for this slice-of-life film. Michael Madsen is the bar owner, who is deep in debt to the town's book-maker and loan shark Burt Young. Chris Penn is one of the bar's main inhabitants as he hides from his failing marriage to Mary Stuart Masterson. The bartender's sister (Virginia Madsen) is about to be married, and her former fiancé (Tom Sizemore) shows up in town, after leaving her at the altar years before. Con man James Belushi runs a con on Perry to steal the money for the wedding caterer. As every plot in this multi-layered story seems to be at its worst, things look up because of an unlikely hero.