Revisiting the Reviled — ‘Jack and Jill’ is Definitive Proof That Adam Sandler Hates You

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Every week with Revisiting the Reviled, Sean looks at a film that was meant to appeal to geeks and failed, often miserably.

Over the past few years, more so than ever before, the films of Adam Sandler and his Happy Madison Productions have become an object of scorn. Sandler’s work isn’t just the target of criticisms because of their regressive humor, rampant product placement, low stakes, and meandering stories – though those are all reprehensible characteristics of a Happy Madison Production – it’s that there’s a feeling of overwhelming laziness that appears on screen, as if it’s a minor miracle that Sandler and company have departed the nestled comfort of apathy to at least present an image in focus. But there was one Sandler film that seemed to be a bridge too far for most movie fans. By playing twin brother and sister in Jack and Jill, Adam Sandler had somehow crafted a movie that insulted the intelligence of movie fans that refused to see the movie, viewing only the asinine trailer, or the George C. Scott parody of it.

The trailer for Jack and Jill was a rare case of truth in advertising. The film is, shockingly, just as you’d expect. However, through all the painstaking moments of a shrill Adam Sandler in drag, there remains a bafflingly committed performance by Al Pacino as himself. Even that committed performance by Pacino can’t salvage the film from being just another painful Adam Sandler movie full of celebrity cameos, product placement, poorly worded innuendo, and a generally regressive attitude towards lower classes and immigrants. In other words, par for the course for Sandler.

After opening with a brief montage of various twins recounting their bond – you see, had this three-minute sequence been cut, Jack and Jill would’ve fallen short of the 90-minute mark to contractually be considered a movie, I guess. After that, Sandler and director Dennis Dugan recycle the grainy 8mm footage that opened their Happy Gilmore years prior, showing us the eponymous Jack and Jill in their youth. After opening with a fair chunk of filler, the film then takes us to the present day. Jack Sadelstein (Sandler) is an advertising exec whose company is running into hard times unless they secure a new Dunkin’ Donuts ad. The corporate overlords at Dunkin’ Donuts want Al Pacino to star in their new ad which features a cappuccino-like name – I sincerely wonder how long Sandler had been saving the cappuccino/Al Pacino joke, probably since the early ‘90s (there’s a similar Mad Magazine gag from the ‘90s that I was unable to track down). Before Jack can worry about recruiting Al Pacino, he has to worry about his twin sister Jill (also Sandler) coming in for Thanksgiving dinner.


The entire setup for the comedy of errors is so clumsily handled that it takes the viewer a little while to figure out just what in the hell is going on. There’s Jack’s wife Erin (Katie Holmes in her most degrading role since marrying Tom Cruise) and their two kids Sofia (Elodie Tougne) and Gary (Rohan Chand), the latter being their adopted Indian son who likes to tape things to his body. COMEDY! Anyway, Jill is her loud self, embarrassing Jack at the dinner table – there’s also an older couple with a homeless man because making fun of the poors is just a laugh riot! Before Jack can rush Jill out to the airport, his twin sister decides to stay in Los Angeles to live it up and fulfill certain bucket list opportunities. While Jill is appearing on The Price is Right and inadvertently crippling ponies, Jack is trying to secure Al Pacino for the Dunkin’ Donuts ad in order to save his company, never mind that he probably could sell his 20-room mansion and stay afloat.

So Jack takes Jill to a Lakers game because he knows that Al Pacino will be there. At the game, Pacino finds himself stricken with Jill. But Jill is uninterested in Pacino. So this sets up a conundrum for Jack who needs Pacino in a commercial and wants Jill to be anywhere but near him. This leads to a hilarious situation where Jack has to dress in drag to meet Pacino. If we’re operating under the assumption that Adam Sandler in drag is funny, then placing him in drag for a second time is twice as funny.


Jack and Jill isn’t merely a wretched movie because of its lowbrow humor. It’s a wretched movie because it’s so lazy and haphazard in its lowbrow that there’s little in the way of anything resembling a joke. For example, two Adam Sandlers performing jump rope next to each other isn’t either amusing or inventive. The same, however, could be said about the sheer number of montages and celebrity cameos. Not only does Sandler make sure to give bit parts to about half of the SNL alums ever, he even makes sure to cram in cameos by his Grown Ups co-star Shaquille O’Neal and his Little Nicky co-star Regis Philbin, among many others. There’s even an extended conversation between Jill and Jared Fogle where the two discuss the many wonders of a Subway sandwich.

For reasons that I’ll never be able to wrap my head around, Jack and Jill had an estimated budget of a whopping $79 million. If you’re able to view what in this film would’ve cost around $80 million dollars, perhaps a career in charter accountancy is for you. Maybe they had the world’s best craft services on set. Regardless of its wildly excessive budget, Jack and Jill will only survive as the definitive proof that Adam Sandler stopped giving a shit a while back. There’s nothing within the film, the eighth collaboration between Sandler and director Dennis Dugan, which warrants viewing. It’s not even so bad it’s good. It’s just bad. This is a film of lazy cynicism. “I’ll just wear drag and the rubes will show up,” I imagine Sandler saying during the scripting process. It’s hard to differentiate the attitude behind Jack and Jill and Sandler’s upcoming The Ridiculous Six. In Jack and Jill, Sandler’s Jill says, “He wants to play Twister with your sister.” In a joke from the script for The Ridiculous Six a character says, “I put my peepee in your teepee?” It’s one thing to recycle jokes; it’s something entirely more insidious to recycle a joke of rhyming innuendo that wasn’t funny in the first place. Then again, that pretty much defines Happy Madison Productions.

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