Nicholas "Oz" Oseransky (Matthew Perry) is a Quebec dentist from Chicago, who happens to be genuinely likable to almost everyone who knows him. However, he is trapped in a miserable marriage to the daughter of his late ex-partner. 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. He can't divorce his wife because her father embezzled from the dental practice, and he has nothing but debt if they separate. As the movie opens, Sophie tells Oz she needs $5000, but won't say what for.At the office, we are introduced to his assistant, Jill (Amanda Peet). Jill and Oz have lunch and she tells him that his wife isn't a good person. They joke about the fact that, due to his insurance, he's worth more dead than alive, and discuss having her taken out of the picture, and Jill playfully tells him to name a price. When Oz gets home, a new neighbor is moving in next door. Oz thinks that "Jimmy Jones" looks familiar, and after recognizing a tattoo on Jimmy's forearm, realizes that he's Jimmy "the Tulip" Tudeski (Bruce Willis). Tudeski is an infamous contract killer from Chicago who was given amnesty after ratting out Lazlo Gogolak and other members of the Gogolak gang.Oz runs home in a panic and tells Sophie they're moving. But Sophie insists that Oz return to Chicago to collect a finder's fee by giving up Jimmy's whereabouts to Lazlo's son, Janni (Kevin Pollak). Oz is picked up by Jimmy in a sudden trip to the city, where he reveals his predicament to Jimmy: his wife's father got involved with an underage boy who blackmailed the father, who embezzled money to pay off his blackmailer, and then committed suicide, saddling Oz with the debt. Jimmy sympathizes with Oz, and tells him he honestly likes Oz. Even though Oz has warmed to Jimmy, he still goes through with the trip to Chicago to pacify his wife. Upon arriving in Chicago, Oz has lunch with an old friend and confesses that he has no intention of meeting with Janni or giving up Jimmy; unfortunately, when Oz returns to his hotel room, he is greeted by Frankie Figs (Michael Clarke Duncan) who turns out to be one of Janni's enforcers. Frankie roughs Oz up to get the truth out of him and then takes him to Janni.At Janni's estate, Oz meets Cynthia (Natasha Henstridge), Jimmy's estranged wife. Janni instructs Frankie to accompany Oz back to Canada and keep an eye on Jimmy until Janni and his men arrive to take him out. Back at the hotel, Oz calls Jimmy in a panic, warning him to run, but Jimmy casually reassures him everything is okay. He is then visited by Cynthia, who asks Oz if he really knows where to find Jimmy, explaining that Janni and Jimmy both want her (as well as each other) dead in order to collect on $10 million, which is being held in trust in their names (the "whole nine yards" of the title). Oz and Cynthia share a bottle of scotch and end up sleeping together. Afterwards, Oz vows to find a way to protect Cynthia from Jimmy.Back in Canada, Frankie and a very nervous Oz enter another hotel room and see Jimmy waiting inside. It turns out that Frankie and Jimmy are old friends and together, are planning to take out Janni and Cynthia; they both praise Oz's genuine personality, his unwillingness to give up Jimmy, and his faithfulness, even to a wife that hates him. Oz returns to work and tells Jill about the events in Chicago. Jill is extremely excited when she finds out Jimmy the Tulip is Oz's neighbor and makes Oz take her to meet him. Jill tells Jimmy that he's her hero and the reason she wants to be a contract killer. She also tells him that Sophie tried to use the $5000 to have Jill kill Oz, but Jill ended up liking Oz after getting to know him (like nearly everyone else does) and refused to follow through on the contract. Jimmy reveals that Sophie visited him while Oz was in Chicago and tried to seduce him into killing Oz, and offers to kill Sophie as a favor to Oz.As Jimmy and Jill discuss the upcoming ambush, Oz gets angry and says that he won't stand by and let them kill Cynthia. Oz is back at home and tries to call and warn Cynthia about Jimmy's plan, but she is already on the way with Janni. When they arrive at Oz's house, Oz gets a chance to warn Cynthia, while she warns him that Janni will kill him after killing Jimmy. The two watch from Oz's garage as Janni's gang walks into the trap.Down the street, Sophie and her new hitter (Harland Williams) are in his car. She is discussing the payment and promises that her mother will pay the remainder of his fee after the job is done; she notes scornfully that she hates and doesn't understand why everyone else who meets Oz seems to like him. The hitter is distracted when he recognized Janni Gogolak heading toward Jimmy's house. When Sophie tells him whose house it is, he realizes what's about to happen, pulls out a gun and exits the car, taking the car keys with him.When Janni enters the house, he is distracted by a naked Jill, and she, Jimmy and Frankie are easily able to kill Janni and his men. Oz and Cynthia make a break for it. Sophie's hitter is in the yard when he hears Oz's car peel out behind him. This draws Jimmy's attention to the window. He has Jill get the mystery hitter's attention and then shoots him. Sophie sees this and runs, screaming, down the street. When they get the body inside, they realize he is an undercover cop.As they start to get a plan together to dispose of the bodies, Oz calls. While they are on the phone, Jill reveals that Oz slept with Cynthia in Chicagoâwhich she thinks is greatâbut it infuriates Jimmy, who feels that friends shouldn't sleep with each other's wives. Oz makes a deal with them that will benefit everyone. Back at his office, he alters the cop's teeth to exactly match Jimmy's. They then put the cop's body and Janni's into Oz's car and set it on fire, rendering the bodies unidentifiable, except by dental records. The next day, two investigators think that Janni and Jimmy are both dead. This allows Cynthia to collect the $10 million, which as a part of the deal, she has agreed to transfer to Jimmy in exchange for her and Oz's lives. The investigators also find the undercover cop's car when they go to check out Jimmy's house. Inside the car is a tape recorder with Sophie and the cop's conversation to kill Oz, the contents of which are more than enough to put Sophie and her mother in prison, even though Sophie tearfully claims that Jill is the killer that she hired to kill the undercover cop, but the cop does not believe her story. Oz, who is observing behind one-way glass, asks if the detectives know a good divorce lawyer, and is reassured .Some time later, after the death certificates have been processed, the key players meet up in the city. While Cynthia and Jill go to the bank to transfer the money, Oz heads to an art museum with Jimmy, where they will be around people and Oz thinks he'll be safe. Jimmy has other plans though and takes Oz (along with Frankie Figs) out on a private yacht. Back at the bank, Jill asks Cynthia to split the money with her and run, leaving Jimmy to kill Oz if he is double-crossed. Cynthia decides that she loves Oz and can't leave him to be killed by Jimmy. Jill tells Cynthia that it was a test, and that Jimmy wants her and Oz to have $1 million as a wedding gift, and the two women make the transfers.On the boat, Jimmy gets the call that the money has been received. He pulls out a gun and points it at Oz. Frankie grins knowingly before Jimmy turns and shoots him instead; Jimmy explains that he had to kill Frankie or Frankie would kill Oz and then potentially come after Jimmy himself or send others after him in the belief that Jimmy had gone soft. Oz is floored, but happy to be alive. He tells Jimmy that it's obvious he's in love with "her." Jimmy acts confused, thinking Oz is referring to Cynthia. In the next shot, Jill runs on the boat and jumps into Jimmy's arms. Oz leaves to meet Cynthia. As soon as he sees her, he asks her to marry him. She looks disappointed and asks if Jimmy told him (about the money), but when Oz asks what she's talking about, she realizes he truly doesn't know and happily agrees to marry him, assuring him they'll be okay financially. In the closing scene, the two newlywed couples are on a hotel balcony overlooking Niagara falls, dancing to a bluesy version of Ira Gershwin's "They All Laughed" as the credits roll.
Output: Question: Who did Oz sleep with in Chicago?, Answer: Cynthia