- Family guy, Jack Sadelstein, prepares for the annual event he always dreads--the Thanksgiving visit of his fraternal twin sister, the needy, and passive-aggressive Jill, who then refuses to leave.
- Jack Sadelstein is a successful advertising executive in Los Angeles, with a beautiful wife and kids, who dreads one event each year--the Thanksgiving visit of his fraternal twin sister, Jill. Jill's neediness and passive-aggressiveness is maddening to Jack, turning his normally tranquil life upside down.—Columbia Pictures
- Jack Sadelstein is a successful ad exec with a loving wife and beautiful kids. For all this, there is one event that Jack absolutely dreads: the annual thanksgiving visit of his deranged, needy, passive-aggressive fraternal twin sister Jill, turning her brothers tranquil life on its head.—Tom Daly
- The film opens with homemade videos of Jack and Jill growing up. As the videos progress, it seems that Jack is the more gifted twin, with Jill constantly trying to get his attention by hitting him, hurting girls around him, etc. The film then goes to an adult Jack (Adam Sandler), a successful advertising executive in Los Angeles with a beautiful wife (Katie Holmes) and two kids, Sofie and Gary.
Jack is incredibly irritated about the holiday visit of his "identical" twin sister Jill (also Adam Sandler), as he has to pick her up at 4:00am. Following a series of problems from the airport to the house, Jack's patience is soon stretched increasingly thin. Jill's neediness and passive-aggressiveness is maddening to Jack, turning his normally tranquil life upside down. Jill starts ruining Thanksgiving dinner by talking loudly, calling one of the guests homeless, and then runs away into the woods near the house with her pet Cockatoo. Jack's wife makes him apologize to Jill & to beg her to come back into the house. Jill says she has a list of things she wants to do before she leaves; she wants to be on a game show, go horseback riding, and do a studio tour. She tells them she has an open-ended ticket and Jill decides to stay until the end of Hanukkah. Meanwhile, Jack's client wants him to get Al Pacino to appear in a Dunkin Donuts commercial.
Jill tries online dating but doesn't get much of a response until Jack poses as Jill and alters her profile, leading her to get over 100 responses. When her date, "Funbucket" (Norm Macdonald), meets her, however, he runs away and hides in the bathroom.
Feeling guilty, Jack takes her to the Lakers game where Al Pacino is supposed to be, in an attempt to talk to Pacino about signing up for the Dunkin Doughnuts commercial. Pacino develops a crush on Jill as he gives her his phone number on a hot dog, written in mustard and ketchup. Jack hopes Jill would leave by New Year's Eve since Jack and his family are going on a cruise.
All of Jack's friends throw him a birthday party and extend it to Jill as well, having never known that he even had a sister. Later, Pacino takes Jill to his home and lets her pick out a cake. The next day, Jill is leaving, until Jack's gardener, Felipe, takes her to the park where he has organized an entire family picnic to have fun. Jill meets Felipe's kids who are without a mom since Felipe's wife died 4 yrs ago. Pacino makes a deal with Jack that he will do the donuts commercial if Jack gets Jill for him. So, to ensure Jill stays, Jack asks her to accompany them for a cruise on New Years. Pacino and Jack strike a deal in which Pacino will do the commercial if he gets a date with Jill.
Jack disguises himself as Jill and goes on the date with Pacino, as he still hasn't told Jill about the deal with Pacino & moreover Jill hasn't shown any real interest in Pacino every time Jack brought his name up. Pacino picks "Jill"from the ship using a helicopter and takes her to a castle. As Jack learns how much Pacino cares about Jill, he realizes that he loves his sister, and races back to the ship. Once there, however, he learns that Jill has gone back home to the Bronx, because she figures out that the only reason Jack asked her to stay and come on the cruise was so that he could pimp her out to Pacino for his commercial deal.
Jill goes to a restaurant with a picture of the twins' deceased mother. Jack and the family show up and celebrate with her. At the restaurant they see an old high school classmate, Monica (David Spade) who attacks Jack's wife, but is stopped by Jill. Afterwards, they go to Jill's house, which Felipe has decorated to declare his love for Jill. She is overjoyed that someone loves her and embraces him. Pacino also shows up at the party - in costume after a performance of Man of La Mancha - to declare his love, but steps aside once he sees that Jill is happy with someone else. The film ends with the commercial that Pacino stars in, promoting a new coffee Dunkaccino as a rap song. Pacino hates the commercial and tells Jack to destroy every copy and threaten everyone who has seen it.
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