Jack and Jill is a 2011 American comedy film directed by Dennis Dugan from a script by Steve Koren and Adam Sandler. The film was released on November 11, 2011, by Columbia Pictures and grossed $149 million against its $79 million budget.
Jack and Jill stars Sandler in a dual role as twin siblings Jack and Jill Sadelstein, the former a Los Angeles advertising executive being visited for Thanksgiving by the latter from the Bronx. Jack is constantly annoyed by his sister, and is horrified to learn that Jill plans to stay after Hanukkah due to an open-ended plane ticket. However, when Jack is demanded by an agency for Dunkin’ Donuts to get Al Pacino (as himself) for a commercial, Pacino becomes affectionate for Jill, making Jack trying to convince her to date the actor despite her disinterest in him. Other stars include Katie Holmes as Jack’s wife and Eugenio Derbez as another love interest for Jill.
Jack and Jill was panned by critics and audiences, and is widely considered to be one of the worst films ever made. At the 32nd Golden Raspberry Awards, the film was nominated for a record of 12 Razzies in all ten categories. It became the first film to sweep the Razzies, winning in each category including Worst Picture, Worst Actor and Worst Actress.
The film features the final film performance of the late Regis Philbin.
In Los Angeles, Jack Sadelstein is a successful advertising executive who lives with his wife Erin and their two kids Sofia and Gary, an adopted Hindu boy. His unemployed twin sister, Jill, lives in her working-class home neighborhood, and has been living alone since the death of their mother. She visits Jack for Thanksgiving and plans to stay until after Hanukkah with an open-ended plane ticket, to Jack’s horror. She annoys her brother at the Thanksgiving dinner, also embarrassing a homeless guest and Erin’s parents, and at a party by staff of his advertising company celebrating the twin siblings. Jill does various activities around the town, such as being a game show contestant on The Price is Right, going horseback riding, and touring a studio. Thinking what Jill needs is a partner, Jack and the kids teach Jill how to use an online dating site. However, her attempts to find a partner render futile.
Jack’s agency client, meanwhile, wants him to get actor Al Pacino to appear in a Dunkin’ Donuts commercial to promote a new coffee called the “Dunkaccino.” Jack takes Jill to a Lakers game with Pacino in attendance. Pacino ignores Jack but is infatuated with Jill, as he and Jill grew up on the same street, and gives her his phone number. Pacino brings Jill to his home, though she is uninterested in him and soon leaves. Jack’s Mexican gardener Felipe, also smitten with Jill, takes her to meet his family at their annual fiesta, where she hits it off with everybody.
Pacino refuses to do the commercial unless Jack gets him another date with Jill, forcing Jack to invite Jill on a cruise he initially planned only for the family. However, she still refuses to see Pacino again, so Jack disguises himself as his sister and goes on a date with the actor. Jill (hearing Pacino’s voice in the background of a phone call with her brother) learns she was invited just so Pacino would do the commercial, and goes back home to the Bronx out of dejection. Feeling guilty, Jack, as well as Erin and the kids, follow her.
On New Year’s Eve, Jill encounters a group of former classmates and bullies, led by Monica, at a restaurant. Jack, Erin and their kids show up, the twin siblings reconciling by conversing in their made-up twin language. When Monica attacks Erin, she is cold cocked by Jill. Pacino arrives and tells Jill that while he has feelings for her, there is another man more worthy of her than himself. She goes home to find Felipe and his children, where they begin a relationship. The television commercial is made, with Pacino starring and singing a rap song, and he disapproves of it.