The movie opens with Charlie Barret (Christopher Walken) walking to his private table in a restaurant, only to see three young men sitting at his table - Avery (Henry Thomas), Max (Sean Patrick Flanery) and Brett (Jay Mohr). Charlie happens to know Avery's father, and after an initial reluctance, is willing to go with the boys for a 'night on the town'. As the scene progresses, it shifts back and forth to the planning of what they're going to do to Charlie - they plan to kidnap him by strapping him to his seat and use some chloroform to knock him out. Naturally, things don't go as smoothly as they wanted, and Charlie tries fighting back - but eventually succumbs and passes out.
When Charlie wakes up, he sees himself surrounded by the three men, and a fourth friend, T. K. (Jeremy Sisto), dressed in a doctor's uniform, checking his vital signs. It's soon revealed that Charlie 'used' to be Carlo Bartolucci, a mob figure. The boys then explain that Avery's sister, Elise (Laura Harris), has been kidnapped, and that the kidnappers (Frank Medrano and Brad Garrett) are demanding $2 million ransom for her release.
They figure that Charlie still has connections to get that kind of money to the gangsters, and they want his cooperation. To ensure that Charlie knows how serious they are, Charlie is shown his pinkie finger, complete with a signet ring, cut off and floating in a bowl of ice - since the same was allegedly done to Avery's sister. Part of the incentive that Charlie help them immediately is that there is a small window of time available where a hospital could successfully sew the finger back on and the clock was running out. Charlie flies into a rage, stating "I'm looking at dead men. " However, he eventually agrees to help them. Part of the reason Charlie decides to help is that it becomes apparent towards the middle of the film that due to lifelong heavy drinking, Charlie has a major deficiency of Vitamin K, a major component needed for the body to form blood clots: Basically meaning that while a normal healthy person would have minimal bleeding after having his pinkie amputated (Especially considering that T. K.
has medical training and bandaged up the wound correctly), Charlie, on the other hand, would continue to bleed to death without proper medical treatment. Charlie then contacts his lawyer, who in turn contacts Lono (Denis Leary), Charlie's bodyguard, asking him to track Charlie down. Lono goes about his own investigation, asking for (and in some cases beating out) information from people, including the hostess, Jennifer (Nina Siemaszko) who usually waits on Charlie, and a friend of Charlie's, Lydia (Laura San Giacomo). During the course of these conversations, an added backstory is shown about both Lono and Charlie, including how Charlie got his signet ring.
Charlie, meanwhile, tries to take the boys' na´vete to his advantage. A fifth friend, Ira (Johnny Galecki) shows up they are in his father's house, and Ira didn't know anything about what they had planned. Charlie starts playing the boys off of each other, slowly getting information out of them, including how they got into this mess in the first place. After much cajoling and piecing information together, Charlie learns that Avery was actually the one responsible for his sister's kidnapping. The boys had, the previous summer, spent a wild weekend in Atlantic City, where they dropped tens of thousands of dollars on various bets. Avery had gotten in over his head wagering on a basketball game, and had to come up with a way to pay off his $50,000 debt.
The two mobsters approached him and told him they would kidnap his sister and take the "ransom" as payment for the debt. Lono eventually makes his way to Ira's house and has Charlie removed from his restraints, around the same time that the money is sent to the two thugs. The next day, Charlie and Lono meet up with the two gangsters who had kidnapped Avery's sister, around the same time that Avery learns that his sister is not at the hospital where she is supposed to have been. Charlie and Lono figure out that Elise had come up with a plan to fake the kidnapping and ask for a $2 million ransom; the thugs would get $1 million for playing along, while Max and Elise would walk away with the rest. Charlie and Lono track Max and Elise to a boat off a tropical island where, although Charlie understands their reasons for conning him, he has Lono kill them both. We see the screen tint orange rotoscope as it goes out of focus, and hear two shots (meaning their deaths).
They have reclaimed the rest of their money.....