Featuring Music By Bob Dylan, Bruce Springsteen and Elvis Costello
The Florentine is a neighborhood bar that serves as the touchstone for a group of friends living in the shadow of a run-down mill town. Whitey (Michael Madsen) has inherited the bar from his deceased father and struggles to keep it in business. In the meantime, he is preparing to give his sister, Molly (Virginia Madsen), the finest wedding that she rightly deserves. But Frankie (Luke Perry) "borrows" the money Whitney has set aside for the wedding to invest in a con man's (James Belushi) fly-by-night scheme and almost ruins the wedding. Teddy Finn (Tom Sizemore), the one friend who left town to travel returns home to see Molly after abandoning her at the altar several years ago. With one courageous act, Teddy saves the wedding for his former girlfriend and his long time frinds. In the meantime, Bobbie (Chris Penn), an ex-boxer turned small-time bookie, loses his girlfriend Vikkie (Mary Stuart Masterson) when he can't stop his petty numbers-running racket. Making the biggest mistake of his life, Bobbie foolishly takes on the real criminals who run the town.
Seeing their dreams and the rituals of adolescence fade, the friends pass from the world they expected to inherit to the one they are living - disappointments and all. The Florentine maps their lives as they discover the hard truths of responsible adulthood and the importance of friendships that money can't buy. As the wedding signals a new beginning for the couple, it also signals a new phase of life for each friend.