In the heart of suburbia, a hit man with heart has just moved in.
Nick is a struggling dentist in Canada. A new neighbor moves in, and he discovers that it is Jimmy "The Tulip" Teduski. His wife convinces him to go to Chicago and inform the mob boss who wants Jimmy dead.
Witness Protection, Fish Out of Water, Unlikely Criminals, Hired Killers, Suburban Dysfunction
Silly, Quirky, Madcap, Goofy, Light, Raunchy, Paranoid
Nicholas "Oz" Oseransky (Matthew Perry) is a depressed, slightly neurotic dentist working and living in Montreal. His wife Sophie (Rosanna Arquette) and mother-in-law (Carmen Ferland) hate him, and his deceased father-in-law has saddled him with a lot of debt. At work, Oz has made friends with his receptionist, Jill (Amanda Peet), who urges him to get away from his wife who she believes is "not a good person". Oz admits that due to his life insurance, he's worth more dead than alive to her, but that he currently cannot afford to divorce her.
Jimmy "The Tulip" Tudeski (Bruce Willis), a hitman, moves in next door under the assumed name of "Jimmy Jones". Having testified against the Gogolak gang, a very dangerous crime family in Chicago, Jimmy is hiding out in Canada. He immediately befriends Oz, who realizes who he is and becomes very nervous around him, but subsequently bonds with him after Jimmy invites him to show him around Montreal.
Sophie presses Oz to travel to Chicago, where he is to meet up with Janni Gogolak (Kevin Pollak), let him know where Jimmy is, and collect a finder's fee. Oz travels to Chicago against his better judgment, but does not go to see Janni. Oz goes to his hotel room and finds another notorious hitman, Franklin Figueroa, a.k.a. "Frankie Figgs" (Michael Clarke Duncan), in his room. Frankie beats up Oz and takes him to meet Janni. It is at this meeting that he first encounters Jimmy's wife, Cynthia (Natasha Henstridge), for whom Oz immediately harbors an attraction.
At the meeting, Janni explains that he intends to find out where Jimmy is, which Oz is coerced into admitting that he knows. Then Janni releases Oz, with the understanding that Frankie will go with him to assassinate Jimmy. Oz returns to his room, and immediately calls Jimmy and confesses everything, apologizing to Jimmy about revealing his whereabouts and imploring him to save himself. Jimmy, sounding unruffled, tells Oz to calm down and says that not only does he already know what happened, but that he also reassures Oz that it's all according to plan. Oz hangs up, and Cynthia arrives at the room. She reveals that some time ago, she, Jimmy, and Janni set up a joint account containing $10 million. There is, however, a special stipulation - the money can only be withdrawn in person by all three principals - or two principals and the death certificate of the third, or one principal with two death certificates. Oz realizes this is Jimmy's plan - to kill Janni and Cynthia to get all the money. Oz and Cynthia then have sex before Oz returns home with Frankie the next day.
Back home, Oz meets with Jimmy, and it is revealed that he and Frankie are friends who are working to betray Janni, whom Frankie has told to come up to Canada himself, simultaneously intending to kill Cynthia. An increasingly paranoid Oz reveals what is happening to Jill, who becomes excited and insists that Oz introduce her to Jimmy.
To Oz's shock, Jill reveals she is an aspiring "hit woman" who idolizes Jimmy. She was hired by Oz's wife to kill him, but after going to work for him (to get a feel for his movements and work out the best time to kill him), she ended up liking him too much to go through with it. Jimmy takes a quick liking to Jill and incorporates her into his plan. Jimmy plans to set a trap for Janni and kill him and Cynthia, which Oz objects to.
On the night of the plan, Jimmy's trap succeeds and he, a naked Jill, and Frankie kill Janni and his men. Oz flees the scene with Cynthia. A short time later, a second hit man, hired by Sophie to kill Oz, is on the front lawn of the house, and Jimmy shoots him dead, causing Sophie to flee the neighborhood in terror. A badge found in the dead hit man's pocket reveals him to be an undercover police officer.
When Jimmy discovers that Oz slept with Cynthia, he becomes enraged, but Oz tells Jimmy he loves Cynthia, and ha