So THAT Happened: Adam Sandler Dressed As His Twin Sister To Get Al Pacino To Rap In ‘Jack And Jill’

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Jack And Jill (2011)

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For the most part, the history of TV and movies has been a wondrous and larger-than-life adventure, expanding our imaginations and our emotions. But sometimes that history has gotten weird. That’s where we come in. Welcome to So THAT Happened, a corner of the internet devoted to dredging up some of the most surprising pop culture moments and reminding you how weird and vaguely disturbing your favorite shows and movies are.

You typically only hear two reactions when Adam Sandler’s name pops up — either a frustrated groan or a happy “Oh!” For the most part, critics fall firmly in the former category. There was a time long ago when Sandler’s work was regarded as genuinely funny, but now the actor and comedian is about as divisive as they come. I think the organization of cinematic criticism discovered that there was a limit to how many fart jokes they could handle, and that limit was reached five Sandler movies ago. However, there are two things that Sandler’s movies consistently have going for them: money and audiences.

All that being said, Sandler’s 2011 movie Jack and Jill reached a whole new level of bad. The movie stars Sandler (of course), who plays the fraternal twins Jack and Jill, as well as Katie Holmes and Al Pacino. Yep, that Al Pacino. This one didn’t just win a Razzie. Jack and Jill was the first movie to ever win every Razzie award for its year. Notably, Sandler won it for both worst actor and actress. There’s a lot to question about this movie, but today, we’re focusing on big picture: the entire plot.

WTF HAPPENED?

Adam Sandler’s character Jack pretended to be his twin sister Jill so that he could go on a date with Al Pacino. And why did Jack want to date Pacino, who was playing himself in this movie? So that Jack/Jill could convince Tony Montana to rap in a Dunkin’ Donuts commercial. None of this is even remotely exaggerated.

HOW IS THIS POSSIBLE?

We’re jumping into the world of Sandler mythology, becasue why not? In the movie, Jack is the responsible and high-achieving sibling who escaped the Bronx and is now a successful LA advertising shark. Jill is basically the opposite of all of that. She’s loud, rude, clueless, and just generally an unsuccessful mess of a human. Throughout the course of the movie, Jack has to learn to embrace Jill’s over-the-top quirks and, as a result, his past and — blah, blah, blah, you know where this is going. All you really need to know is that Jill is obnoxious and has stayed with her brother far past her welcome.

While navigating the annoying hurricane that is his twin sister, Jack is also balancing a big work account with Dunkin’ Donuts. The doughnut chain really wants Al Pacino in their newest campaign becasue they really love puns (they have a new product called a Dunkaccino), and all eyes are on Jack to recruit the cinematic gangster. Pacino says no, becasue his onscreen character makes better business choices than the real life Pacino. That is, he says no until he sees Jill. Pacino becomes fascinated by Jill and agrees to the commercial only if he can score a date with Jill.

That’s how Jack ended up posing as his twin sister to schmooze Michael Corleone into rapping for Dunkin’ Donuts. It doesn’t exactly work out. Pacino proposes to Jill, who turns him down, and when Pacino sees the advertisement, he immediately tells Jack to destroy all copies. But Jill found love and Jack learned more about his sister so … lesson learned?

NO, HOW WAS THIS POSSIBLY CREATED?

Because Adam Sandler. Sandler is one of those few creators who is allowed to roam Hollywood freely simply because his stuff gets results. Jack and Jill made over $149 million worldwide with a budget of $79 million. Just be happy we’ll likely never see a Jack and Jill 2.

[Where to stream Jack and Jill]

Photos: Everett Collection