High school junior high school student, Joel Goodsen (Goodman) is thrilled when his parents take off for a vacation for some days. Shortly after an attempt at getting a cheap prostitute going goes a little awry, Joel gets out with his new girlfriend, fifteen year old Alexa (Jennifer Aniston). However, shocked by the large amount of money handed over to him by his parents, Joel decides to hire a pimp to work for him. Worried about leaving his own daughter alone, Joel’s pimp, Cash (James Russo) crashes the wedding of his friend’s daughter, Lexie (Daphne Guinness). Forced to return home, the guilt-ridden Cash flees through town, but is captured and taken back to his ‘home’ by vicious dogs.
When the police find the bodies of both girls, Joel, desperate to get his hands on Cash, is given thirty million dollars by his friend, Johnnie (Philip Seymour Hoffman). Although this amount may seem peanuts compared to the $500 million pocketed by the mob in The Godfather II, Joel’s greed soon gains him the attention (and sometimes the ear) of the boss, Mob boss Leo (John Turturro), who is tired of getting ripped off. Now, in order to get some of the billions he owns, he’s willing to sell ninety percent of his stake of the company to a firm run by his friend, Carl (David Strathairn). But in order to secure his share, Joel must put up a risky business with a conscience and a thirst for adventure…
Meanwhile, back at home in New York, a call girl named Rebecca de Mornay (Sandra Oh), whose past experiences with a serial killer remind her of what she’s experienced in her own life, gets an invitation from the mob boss to an inheritance she is supposed to receive. Before she can attend, however, she is kidnapped by two men, Brickman (Philip Seymour Hoffman) and Bob Seger ( emitting a dreadful whistle that scares away the women). In exchange for the money she holds, they agree to help her escape.
Once at the safe-keep of the ‘royalty family’, the fortune which awaits Rebecca de Mornay is quickly squandered when the head of the family dies of a heart attack caused by a bullet meant for Joanne. Now, in order to recover the money which has been left for Joanne, Brickman hires his son, Bob, to kill her rival, Bob Seger. Having no other choice, Bob shoots Joanne in the head and kills herself trying to save Brickman. With this opportunity for revenge, Brickman enlists the help of his old friend, Paulie (James Belushi), whom he has had a romantic affair with since grade school and wants to get back together with. Meanwhile, his son Charlie ( Daniel Grudich ), who is obsessed with killing the boss, uses a machine to shoot dead the heads of Joanne’s bodyguards.
When Joanne’s bodyguards open fire on the two men, they are confused because they thought it was simply a set-up for another robbery which will go as planned. As the tension builds between the two, the call girl begs her mother not to leave and asks them to protect her. She then tells them about a man called Brickman who owns a hardware store where she once worked and frequented. Joanne realizes that the two men are after her money and decides to make a run for it.
A number of different things happen to take place throughout the film, the main theme is jealousy. The women are constantly trying to get Joanna and Brickman’s attention while at the same time making sure that Joanna gets the attention she deserves. The fact that they are running a risk of getting thrown into jail and having their reputations damaged further pushes them to take extreme measures. However, when the two finally corner the owner of the brothel and his wife, they realize they have more in common than what they were expecting.