For all of her failings, Jill is very sincere about her love for Jack and his family. She longs to be connected to them, and she expresses a desire to have her own family just like their family. When young Gary asks his aunt why she doesn't have children, Jill explains that she never married and that that's a prerequisite for having kids and a happy family.
Indeed, Jack has a loving relationship with his wife, Erin, and their kids. But he balks at Erin's suggestion that he open up more to his sister. Eventually, though, (with Pacino's help) Jack comes to an understanding of his special relationship with Jill. And he goes to great lengths to demonstrate his love for her.
The Sadelsteins' gardener, Felipe, invites Jill to his family picnic and publicly praises the members of his huge Mexican family. In recorded segments at the beginning and the end of the movie, real-life twins express their bond and love.
It's stated that Jack's wife converted to Judaism. After his assistant repeats one of Jack's self-deprecating statements about Jews, Jack rebuffs him, pointing out that he can't say those kinds of "insider" things since he's not Jewish. The assistant replies, "But I'm close. I'm an atheist!" There's a gag about Pacino (disguised in a full beard) looking like a rabbi.
At a party, Jack tells Jill that his assistant doesn't believe in God, and she and John McEnroe start yelling at him. Pacino tells Jill, "Oh ye of little faith." She asks, "Is that Shakespeare?" He replies, "No, Jesus." While on the phone with his assistant, Jack snorts, "God told me your feet were on my desk. Get 'em off!"
Women on a cruise ship wear skimpy bikinis. Elsewhere we see very low-cut dresses and other revealing tops. A woman at a New Year's Eve party reports, "I'm not wearing any underwear." Another woman announces that she works at Hooters, as she grabs her clothed chest. Jill makes comments about two "hookers" at a party. And at Felipe's picnic, she dances and shakes her clothed breasts. An old man in the crowd grabs her backside. Another guy manages to look up her skirt, reporting to his friend, "It's not a guy."
When thinking about a good user name for a dating site, Jill says, "How about Manilow? 'Cause he can use me anytime." Later, after Jill fails to receive any responses on the site, Jack secretly posts a sexual innuendo-laden ad on Craigslist to stir up lots of responses for her. But Jill balks at Jack's suggestion that she date Al Pacino, saying, "All he wants to do is play Twister with your sister!" Pacino smirks over the phone, "I can smell horny across an ocean!"
In desperation, Jack scrambles into a public bathroom and dresses up as his sister to have a date with Pacino. He fills her bra with two cantaloupes, and when he steps out of the stall, the bathroom attendant motions him over and adjusts his melons so they look right. Later, Jill is standing in the hallway and the bathroom attendant spots her and mistakenly gives her another adjustment.
Jill immediately punches the attendant back through the bathroom door. An inebriated Jack punches Pacino in the face, and Pacino returns the favor, breaking a chair across Jack's back. A drunken woman puts Erin in a headlock and starts swinging her around. Jill steps in, throwing the woman into a wall and punching her in the face.
While staying with Jack's family, Jill wants to go with them to a number of fun activities—and the results are almost always disastrous. For instance, when the kids ride on ponies, Jill insists that she's not too heavy to join them … and crushes the pony flat. Then they visit The Price Is Right and Jill knocks herself out with the big prize wheel. She rides the family's Sea-Doo in the pool and flies up out of the water, crashing down on the lawn furniture.
At Thanksgiving dinner, talk turns to the sometimes physical connection between twins. Jill starts slapping herself in the face to see if Jack can feel it. He says he can't, so Gary slugs her on the jaw and knocks her backward off her chair. "Did you feel that, Daddy?" the kid gleefully asks. At the picnic, Felipe's bug-eyed grandma gets pummeled repeatedly as Jill's shoe flies off and conks her, and a swinging broom handle knocks her out cold.
Drug and Alcohol Content
People (and the cockatoo) are seen drinking bottled beer, mixed drinks and/or Jack Daniel's on a cruise ship. Wine and spirits show up at a party and several dinners. Jack (pretending to be Jill) slugs back quite a lot of the hard stuff on his "date" with Al.
Other Negative Elements
Where to begin. Where to begin. Racial stereotypes make the joke list. Toilet humor involves Jill's sweat-stained sheets, her abundant flatulence, her body hair, her body mass, her ear wax, etc. An example: When Jill returns from Felipe's party after eating Mexican food for the first time, she scampers out of the car yelling, "It's the chimichangas! They're making a run for the border." We then hear a cacophony of gassy explosions from the other side of the bathroom door (and witness the odorous aftereffects).
Jill talks about her period to her niece and nephew. She tells Jack's office friends about his bedwetting tendencies as a child. We see her and Jack doing synchronized crotch scratching and wind breaking.
After Gary watches his dad upload the sexually themed ad on Craigslist, and listens as Jack reports that Jill is wondering what she'll wear for her date, the boy blurts, "What are you gonna wear, Daddy … in hell?"
To say Jack and Jill is ridiculous and obnoxiously lowball gives it too much credit. This is just a lazy mess of a movie that targets cross-dressing, bodily functions, Mexicans, Jews, hookers, fat women and anything else it can focus its snickeringly meanspirited gaze on—all while pretending to shoehorn itself into a holiday setting.
Forget about Adam Sandler's intentionally stupid shtick. Even Al Pacino's self-mocking antics feel forced and foolish here. Add in a motley cadre of celebrity cameos—from Johnny Depp to Regis Philbin to David Spade—and you've got a flick that looks like it could have been tossed together over several long weekends. Long weekends packed with lots of "Oh, this'll be funny" improvs and a couple of coolers full of adult beverages.
Truth is, the funniest and most endearing parts of the movie are the opening and closing snippets of actual twins talking about their experiences together and their feelings of loving connection. Those short "candid" moments hint at how good this twins idea could have been. But unless you're a diehard Sandler-in-drag fan who likes your humor gassy and your jabs racist, well … do I really even need to finish that sentence?