The Florentine (1999)

Synopsis
The regulars at a shot-and-a-beer bar in a decaying working-class town are the focus of Nick Stagliano's drama The Florentine. Michael Madsen plays Whitey, who owns a bar called The Florentine where most of the guys he knows hang out. His sister Molly (Virginia Madsen, Michael's real life sister) is soon to be married, and Whitey has been saving up for a nice reception. But when her old boyfriend Teddy (Tom Sizemore) comes back into town, bets for the wedding would seem to be off, which may be just as well -- Whitey's buddy Frankie (Luke Perry) got hold of the wedding cash and lost it to Billy Munucci (James Belushi), a con artist with a far quicker turn of mind. Whitey has other money problems; the bar has been mortgaged to a low-level gangster named Joe (Burt Young), who has been leaning on Whitey's friend Bobbie (Chris Penn) to pay off his mounting gambling debts. Bobbie is trying to stay one step ahead of Joe, which doesn't leave him much time to patch up his ailing marriage to Vicki (Mary Stuart Masterson). The screenplay by Damien Gray and Tom Benson was adapted from the Off-Broadway drama penned by Gray. ~ Mark Deming, All Movie Guide