The Florentine (2000)

A slice-of-life story unfolds inside The Florentine, a bar in a Pennsylvania steel town whose brightest days are behind it, leaving behind many of life's disillusioned "losers." Its owner, Whitey (Michael Madsen), is deep in debt to the town's loan shark, Joe McCollough (Burt Young), and desperate for a path forward which won't cost him the bar. His sister, Molly (Virginia Madsen), is days away from her long-awaited nuptials, and then her former fiancé, Teddy (Tom Sizemore), shows up in town for the first time since leaving her at the altar years before. Ne'er-do-well Billy Belasco (Jim Belushi) runs a con on Frankie (Luke Perry) to steal the money for the wedding caterer, while long-time regular Bobby (Chris Penn) becomes a patron-cum-inhabitant as he hides from his fast-crumbling marriage to Vikki (Mary Stuart Masterson). Every plot in this multi-layered story seems to be at its nadir just as a pair of unlikely heroes emerge out of the backdrop to turn everything around.