It is the movie that swept every single category at the Razzies. Literally all of them. When people talk about the cast of Jack and Jill movie, they usually start with a sigh or a bewildered laugh. Released in 2011, this Adam Sandler vehicle became a sort of legend for being, well, exactly what it is.
But honestly? Looking back at the lineup today is surreal. You've got an Oscar-winning legend, a Batman Begins star, and enough sports cameos to fill an entire season of ESPN. It makes you wonder how a project this panned managed to gather such a specific, high-profile group of people.
The Dual Role: Adam Sandler as Jack... and Jill
The core of the movie rests entirely on Sandler's shoulders. He plays Jack Sadelstein, a high-strung, successful ad executive in Los Angeles. Then, he puts on a wig and some spanx to play Jill, Jack’s "passive-aggressive" twin sister from the Bronx.
Sandler has always liked playing multiple characters, but this was different. Usually, there's a bit of a wink to the audience. Here, the humor mostly comes from Jill being loud, sweaty, and physically destructive. According to director Dennis Dugan, they didn't want to go the "Mrs. Doubtfire" route with heavy prosthetics. They wanted Jill to basically look like Adam Sandler in a dress. It’s a choice that definitely defined the movie's vibe.
The Al Pacino Question
If you search for the cast of Jack and Jill movie, the biggest "wait, what?" moment is always Al Pacino. He doesn't just have a cameo. He is a lead. He plays a fictionalized, slightly unhinged version of himself who becomes obsessed with Jill.
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For years, people asked: Why? Why would the man from The Godfather and Scarface do this?
We finally got the answer recently. In his memoir Sonny Boy (and a 2024 interview with The New York Times), Pacino admitted he was essentially broke at the time. His accountant had been involved in a Ponzi scheme and ended up in prison, leaving Pacino with zero dollars. He needed a paycheck, and he needed it fast. Sandler called, offered him a lot of money, and Pacino took it.
He actually seems to have had a good time, too. He famously performs the "Dunkaccino" rap for a Dunkin' Donuts commercial within the movie. It’s a scene so bizarre it has become a massive meme. Pacino even said he loves Sandler and considers him a great friend now.
Katie Holmes and the Family Dynamic
Katie Holmes plays Erin Sadelstein, Jack’s wife. Coming off a string of indie films and her role as Rachel Dawes in Batman Begins, this was a return to big studio comedies for her. Her role is mostly to be the "straight man"—the calm, patient center of a household that is rapidly falling apart because of Jill's antics.
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The kids in the family were played by:
- Rohan Chand as Gary, the adopted son who likes to tape things to his body.
- Elodie Tougne as Sofia, the biological daughter.
It’s a classic Sandler movie setup: a beautiful home, a patient wife, and a whirlwind of chaos entering through the front door.
A Who's Who of Cameos and Side Characters
The cast of Jack and Jill movie is essentially a graveyard of 2011 pop culture. Seriously, look at this list. You have:
- Eugenio Derbez: He plays Felipe, the gardener who eventually becomes Jill's love interest. He also plays Felipe's grandmother, Juangelina.
- Nick Swardson: A Happy Madison regular, playing Todd.
- David Spade: He appears in drag as Monica, a former schoolmate who gets into a fight with Jill.
- Norm Macdonald: In a truly strange role, he plays "Funbucket," a guy Jill goes on a blind date with. He spends most of his screen time hiding on a bathroom ceiling to escape her.
- Tim Meadows: Plays Ted, one of Jack's office colleagues.
Then there are the "blink and you'll miss them" appearances. You've got Johnny Depp sitting courtside at a Lakers game wearing a Justin Bieber shirt. You’ve got Regis Philbin in his final film role. Shaquille O’Neal, Drew Carey, and John McEnroe all pop up. Even Caitlyn Jenner (appearing as Bruce at the time) has a moment.
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Why This Cast Still Gets Talked About
Most bad movies are forgotten. Jack and Jill isn't. People still look up the cast of Jack and Jill movie because it represents a specific era of Hollywood where Adam Sandler’s influence was so massive he could get Al Pacino to rap about hazelnut lattes.
It was a box office success in a weird way, too. It cost about $79 million to make and brought in over $150 million worldwide. Despite the 3% score on Rotten Tomatoes, people watched it. They watched it because the cast was fascinatingly eclectic.
If you’re planning a rewatch—or a first watch out of morbid curiosity—pay attention to the background actors. You’ll see Allen Covert as a homeless man named Otto (a nod to his Happy Gilmore character) and various members of Sandler’s real-life family, like his wife Jackie and daughters Sadie and Sunny.
To get the most out of the experience, don't take it seriously. It’s a time capsule. Watch for the Dunkaccino scene, look for the weird cameos, and appreciate Al Pacino’s commitment to a role he took just to pay the bills.
Check out the full credits on IMDb if you want to see the literal dozens of other athletes and TV personalities who snuck into the background. It’s a deeper rabbit hole than you’d expect.