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Nicholas Oseransky (Matthew Perry), Oz to his friends is a very nice guy... a dentist in a quiet practice in Montreal, with a wife from hell and a mother-in-law to match. Oz's world turns upside-down when he meets his new next-door-neighbour, Jimmy Jones, or, as he is affectionately known in his old Chicago gangster circle, Jimmy the Tulip (Bruce Willis).

Jimmy the Tulip was a hit man for the Gogo Gang. He ratted out mob boss Charlie Gogolack and is now hoping for a quiet life in suburban Montreal. However, Oz's scheming wife (Rosanna Arquette) puts an end to that by making Oz fly to Chicago to turn Jimmy into the mob and collect a finder's fee. Oz agrees to her plan, hoping that perhaps the money will allow him to pay off her debts and be rid of her.

In Chicago, Oz is surprised to find Frankie Figs (Michael Clarke Duncan) waiting for him at his hotel. Frankie works for Jojo Gogolck, who has put out a contract for Jimmy. Jojo is holding Jimmy's wife, Cynthia as a sort of hostage hoping she will lead them to Jimmy. One look at Oz and Cynthia forgets all about Jimmy... it's love at first sight! Meanwhile back in Montreal, Oz's dear wife Sophie has not only told Jimmy the Tulip where Oz has gone and why, she has also hired a hit man to get Oz when he returns to Montreal.

In a hysterical finale, guy shoots guy, a new identity and a new girlfriend is obtained, but does everyone live happily ever after?

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