In an Italian neighborhood of Greenwich Village, Charlie Moran, Mickey Rourke, a maître d'hôtel with aspirations of someday owning his own restaurant, and Paulie Gibonni, Eric Roberts, a bungling schemer who works as a waiter, live with expensive tastes but not much money. Paulie gets caught skimming checks, and both men are fired. Now out of work and in debt, Charlie must find another way to pay his alimony, support his pregnant girlfriend, Diane, Daryl Hannah, and try to buy a restaurant.
Paulie comes to Charlie with a seemingly foolproof robbery idea involving a large amount of cash in the safe of a local business. Charlie reluctantly agrees to participate, and they manage to recruit Barney, Kenneth McMillan, a clock repairman and locksmith, to help crack the safe. The plan gathers momentum as the trio pulls off the break, but it soon spirals into trouble, drawing in more dangerous players and setting off a chain of consequences that neither Charlie nor Paulie anticipated.
The operation goes sour when a police officer, Walter "Bunky" Ritter, is accidentally killed, and it turns out he had been secretly taping Bed Bug Eddie Grant. Charlie learns that the money they stole belongs to Eddie, a figure entrenched in the local mob world, and the realization pulls the friends deeper into a dangerous game. Eddie’s crew moves quickly, and Paulie finds himself stuck between loyalty to family and the brutal demands of the mob. The consequences are immediate: Eddie’s henchmen cut off Paulie’s left thumb as punishment, underscoring just how quickly missteps can become life-changing losses.
Diane makes a painful decision, leaving Charlie with his money and a future that suddenly looks uncertain, while Paulie is forced to work as a waiter for Eddie. He eventually names Barney to the mob, but at first refuses to identify Charlie as the third man involved. Under mounting pressure, Paulie does reveal the truth, Barney flees town, and Charlie mails him his share of the loot, clinging to a fragile thread of hope. As Charlie finally turns a small profit, making about $20,000 on a horse, the dream of stability flickers back into view.
With a tentative sense of control, Charlie prepares for a final confrontation, armed with a copy of the police tape that could expose Eddie. Yet in a twist of calculated desperation, Paulie adds a last-minute twist—lye in Eddie’s coffee—before both men walk away from Greenwich Village, leaving behind the wreckage of misjudged loyalties and a neighborhood forever haunted by what nearly happened. The film ends on a cautiously resilient note, as Charlie contemplates what it takes to chase a dream in a place where old ties pull just as hard as new ambitions.
