The Best Movie Ever | Best Adam Sandler Movies

Adam Sandler is beloved many, hated by some, and probably one of the most controversial figures in contemporary cinema. His broad comedies are offensive and smug, arguably mean-spirited. But they reach audiences of millions who genuinely enjoy them, and who remain impervious to increasingly impassioned criticism lobbed at Sandler by film critics the world over. 

And although many of his movies are despised, including by the critics at Crave, he has made some good ones. The Wedding Singer remains his biggest breakout hit, and combined his brand of 1980s nostalgia and easy target humor with a genuinely sweet romantic comedy narrative. Happy Gilmore still makes a lot of people laugh, and they don’t even seem to feel guilty about it. But what, dear readers, is The Best Adam Sandler Movie Ever? (Hint: It’s not Pixels.)

Related: ‘Pixels’ Review: Now You’re Playing With Pedestrianism

We asked Crave’s film critics – William Bibbiani, Witney Seibold and Brian Formo – to present their picks for the best Adam Sandler movies, and for only the second time in the history of this long-running column, they have all agreed on a single film. (It may be the only thing that Adam Sandler has in common with Dame Judi Dench.) Find out what they picked, and their reasons why, and come back next week for an all-new, all-debatable installment of The Best Movie Ever!

Best Adam Sandler Movies Ever

Witney Seibold’s Pick: Punch-Drunk Love (2002)

Adam Sandler is dreaded by critics. After the pile-up of Big Daddy, The Waterboy, Little Nicky, Mr. Deeds, The Animal, Anger Management, Eight Crazy Nights, 50 First Dates, Click, You Don’t Mess with the Zohan, I Now Pronounce You Chuck & Larry, Grown Ups, Jack & Jill, That’s My Boy (perhaps the most loathsome of the bunch), Grown-Ups 2, and Blended, critics have come to expect very little from the man. I have met a few people who half-heartedly defend a few of his comedies – most are willing to give Happy Gilmore a pass, and The Wedding Singer is mercifully charming – but I have met no one who is completely enthusiastic about Adam Sandler. 

And it’s easy to see why. Sandler’s oft-repeated on-screen comedic persona is an abrasive and obnoxious human being. He berates the women he meets, abuses others, and actively looks down on minorities, old people, and anyone else who isn’t immediately within his social circles. He is also fixated on the pop iconography of the 1980s in an unhealthy way. But rather than view his characters as bitter sociopaths, we’re meant to see them as aw-shucks good-old-boys who just require a little understanding. 

One film managed to bring out Sandler’s psychopathic persona, but actually view it as a pathology. Paul Thomas Anderson’s 2002 film Punch-Drunk Love takes the Sandler myhtos and exposes all the hate, rage, and horror that is right under the surface. Sandler plays a quiet, socially awkward nerd named Barry, who has been picked on and pecked by a gaggle of sisters his whole life, and who is given to occasional bouts of destructive rage; he trashes bathrooms and smashes windows when he can no longer remain calm. He has two notes; quietly awkward and full-bore volcano. And yet, he finds someone who understands him in the form of an equally strange (and just as secretly wrathful) Emily Watson. 

It’s a dissection of all comedy, and how much comedy can be based in anger. It’s the only film to underline what Adam Sandler is really about.  

William Bibbiani’s Pick: Punch-Drunk Love (2002)

Whatever you do, don’t feel bad for Adam Sandler. His movies might, by and large, be hated by “serious” moviegoers the world over, but he makes a lot of other people happy and he makes millions of dollars doing it. But I do sometimes wonder if Sandler really wanted to confine himself to mainstream poop joke movies or if he just settled into it after Punch-Drunk Love didn’t take off. Paul Thomas Anderson’s film was praised by some, confused most others and failed to attract the crossover audience that, clearly, it needed.

I consider Punch-Drunk Love to be the best film of the last decade (2000-2009), and I stand by that assessment. Anderson’s film is a unique entity: mystical, realist, funny and sad, inventive with purpose and meaningful beyond expectation. Even the plot is a bafflement: Sandler plays a novelty toilet plunger salesman with serious emotional problems, beset since childhood by overbearing sisters, who finally finds love just as he also becomes the target of a dangerous mattress salesman/phone sex entrepreneur. Oh, and our hero also plans to take advantage of an enormous loophole in a chocolate pudding sweepstakes.

It’s a confluence of strange situations that Anderson films with all the fine-tuned chaos of a nervous breakdown. There is reasoning to Punch-Drunk love but it must emerge from nonsense, and sometimes it even whispers from the pudding cups. Much has been made of Sandler’s expert dissection of his own abrasive persona, but more should be made of the film’s whirligig kaleidoscope of anxious energy. This film is about a boring life brought to the brink, and that’s a universal quality Anderson exposes with distinction. There’s nothing like Punch-Drunk Love, but everyone and everything can relate to its events.

And I wonder: if the film had made more money, or if it had just won a small handful of awards, if we’d seen more of this kind of experimentation from Adam Sandler, and if the word might have been spared from the horror of Jack & Jill.

Brian Formo’s Pick: Punch-Drunk Love (2002)

Let’s talk about people who love Adam Sandler. No, not the unwashed masses (and not me)—our greatest living American directors! Martin Scorsese, Quentin Tarantino, and Paul Thomas Anderson have all attempted to make Adam Sandler a serious thespian. Scorsese in a Rat Pack biopic that never got made, and Tarantino originally cast Sandler as “The Bear Jew” in Inglourious Basterds, but Eli Roth pinch-hit at the last minute and picked up the Nazi-bashing bat that had long been reserved for Sandler. With Punch-Drunk Love, Anderson is the only great American auteur who has gotten into the Sandler sandbox and called “action!”

At the time, following Boogie Nights and Magnolia, many thought that Sandler’s casting was an attempt by Anderson to pound a square into a peg and see if he could get himself a larger audience via the bankable Sandler—but Anderson maintained that he was a fan, and routinely watched Billy Madison, The Wedding Singer and Happy Gilmore. And with Punch-Drunk Love, Sandler seemed to scratch his art-house itch and decided to hit it and quit it, because his fans didn’t follow him away from the 25-screen megaplexes to screens filled with Jeremy Blake painting scene segues. It’s too bad, because with Love, Anderson does show the appeal of Sandler. As Barry Egan, Sandler is immensely rootable. 

Punch-Drunk Love takes the anger that the 90s Sandler persona had and redirects it inward. Egan beats himself up. But he is a good guy. And when he allows himself to pursue love, his goodness comes out in tap dances, pillow talk, and violent protection. Punch-Drunk Love adeptly captures the goofy feeling of initial infatuation and the need to keep seeing someone. I even fell for Sandler. That side of the bed didn’t stay warm for long, but as far as one-night stands go, Punch-Drunk Love is still amazing to revisit and gives you that giddy feeling, “he needs me, he needs me, he needs me!”

Let us know what you consider to be the best Adam Sandler Movies ever in the comment section below!

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