Nicholas "Oz" Oseransky (MATTHEW PERRY) is a mild-mannered dentist living in suburban Montreal. Although he's not particularly happy about his failing practice - courtesy of his former father-in-law partner racking up a huge debt - or his failed marriage to Sophie (ROASANNA ARQUETTE), a spoiled French Canadian who'd like him dead, things could get worse. After all, a former hit man could move in next door.
That's exactly what happens when Oz goes over to greet his new neighbor only to quickly identify him as Jimmy "The Tulip" Tudeski (BRUCE WILLIS), a hit man who testified against a dangerous Chicago crime family fronted by Janni Gogolak (KEVIN POLLAK). When Sophie gets wind of this, she commands that Oz travel to Chicago, inform the Gogolaks of Jimmy's whereabouts, and collect a finder's fee for their efforts.
Willing to do anything to get away from his obnoxious and demanding wife, Oz then travels to the windy city, but is intercepted by the hulking Frankie Figs (MICHAEL CLARKE DUNCAN), who then takes him to see Janni. There, Oz not only meets Jimmy's estranged wife, Cynthia (NATASHA HENSTRIDGE), but also learns of a former three-way deal between her, Janni and Jimmy where the survivors, or survivor, of the trio will collect ten million dollars.
Oz, who's actually grown to partially like Jimmy - and vice-versa - reluctantly returns to Canada knowing that Janni and Jimmy will try to kill each other and then Cynthia. The only problem is, Oz has fallen for Cynthia. As the various participants' plans are set into motion, Oz must contend with surprising revelations about Jill (AMANDA PEET), his dental receptionist, and agent Hanson (HARLAND WILLIAMS), a local cop, while worrying about what Janni and Jimmy, not to mention his wife, might have in store for him.