In a November 2000 piece about Adam Sandler, Los Angeles Times reporter Paul Brownfield speculated about the future of the former Saturday Night Live funnyman. He’d made the jump to the big screen, starring in a series of hits in the mid-to-late 1990s — Happy Gilmore, The Waterboy, Big Daddy — but he was about to release Little Nicky, a rare bomb in the midst of that winning streak. What was next for Sandler? Brownfield mentioned one potential project, which seemed so utterly bizarre as to possibly be a joke: “The most interesting prospect has Sandler teaming with director Paul Thomas Anderson (Boogie Nights, Magnolia) in a romantic comedy that Anderson has written with Sandler and actress Emily Watson in mind. … On its face, the teaming of Sandler and Anderson is fascinating, if improbable. … The film would marry a writer-director who traffics in emotional risk, whose last movie had Tom Cruise moaning his guts out in grief, with a comedian who hides behind any number of adolescent masks. Would Sandler put down the water pail and emote?”

Two years later, the improbable came true: On October 11, 2002, Punch-Drunk Love hit theaters, proving for the first time that Sandler could be a deft dramatic performer. The film tanked, some critics were confused, but on its 20th anniversary, it’s clear that Punch-Drunk Love remains a career high point for both its star and its maker. Most know that Anderson had long championed Sandler — way before it became fashionable to do so — but the exact aha moment that led to Punch-Drunk Love is not as well-documented. It all goes back to the fall of 1993 and a SNL sketch called “The Denise Show.”

When Sandler was hired on the show in 1990, it was as a writer. But he wanted to be in front of the camera, his goofy persona belying an ambitious streak. “I was very driven, man. … I wanted the Eddie Murphy. I wanted that,” he said in 2020, meaning that he aspired to be a breakthrough talent. The following year, Sandler started appearing on SNL on a regular basis, becoming an official cast member on the season that started September 25, 1993. It was during that season’s second episode, hosted by Shannen Doherty, where he premiered “The Denise Show.”

The premise was simple enough: Brian (Sandler) is a typically brokenhearted young dude smarting over the fact that his true love Denise (Doherty) has dumped him, and so he’s hosting a show in which he works through his sorrow and rage. He takes calls from friends who have seen Denise around town, asks the audience Denise trivia questions and occasionally calls Denise just so he can hang up on her when she picks up. He’s spiteful but basically harmless — what’s obvious is that the joke is on this stilted manchild, who can’t let go of this woman who doesn’t want anything to do with him. As part of the sketch, Brian’s dad (Phil Hartman) phones in, berating his kid to stop embarrassing himself. Brian, in typical Sandler fashion at that stage of his career, goes ballistic. 

“The Denise Show” was very indicative of the pre-Hollywood Adam Sandler, this explosive id exuding boyish energy that could be endearing or disturbing. With characters like Opera Man, Sandler seemed concerned only with getting big laughs by being as silly as possible. It was juvenile, but it could also be really funny. And when he started starring in his own movies, he carried that spirit into Billy Madison, Happy Gilmore and The Waterboy, playing big kids who never grew up. Sandler could carry a broad comedy, but there wasn’t much evidence that he could evolve beyond that.

Paul Thomas Anderson thought differently. Making his name with auteur-driven indie movies such as Boogie Nights, he announced himself as a serious, era-defining filmmaker, indebted to previous American masters like Martin Scorsese and Robert Altman. His films could certainly be funny, but it was clear he aspired to craft bold, brash masterpieces — he was after art. And yet, the guy loved Sandler. In a 2002 interview with Roger Ebert, Anderson tried to sell the venerable critic (and longtime Sandler skeptic) on The Wedding Singer, Big Daddy and Happy Gilmore. “I could watch them over and over and over again,” Anderson declared, “just from the pure joy that you can feel them putting into making the movie, which is just as much joy as you can feel Robert Altman putting into making Nashville.” 

He was taken to making such sweeping statements at the time, although his Sandler fandom was real. (“If I’ve ever been kinda sad or down or whatever,” Anderson said in that same interview, “I just wanna pop in an Adam Sandler movie.”) But it wasn’t until he started working on 1999’s Magnolia that he decided that he needed to write something specifically for the comic. Befriending Cruise while working on that film, Anderson learned that his star had Sandler’s telephone number. Years later, Sandler would relate what happened next: “Tom called me up, and he says, ‘I’m doing a movie with my friend Paul, and he’s a great director and he’s interested in doing a movie with you. Can I put him on the phone?’ Paul was very nice, and he’s going, ‘Hey, I loved Billy Madison.’ And I was like, ‘Okay, thanks,’ but I didn’t know who he was. He goes, ‘I just love your movies and your albums. Is it okay if I write you a movie?’ I said, ‘You can do whatever you want, man.’ He was sweet. I could tell he was funny.”

But what kind of movie could Anderson do with Sandler? What kind of character should he play? The filmmaker got an idea after watching a DVD best-of compiling Sandler’s most memorable SNL sketches, which included “The Denise Show.” Anderson was enraptured by that moment when Brian’s dad calls to berate him. “Adam goes into this fit of rage, screaming at his father,” Anderson told Ebert, “and honest to God I saw this moment where it appears as if the whites of his eyes turn black and they roll back in his head. It was like he just lost his mind. I would play it back, over and over again, and you can see him kinda snap back to reality. The audience is laughing and it’s almost like he finally started to hear them laughing a few seconds later.”

“The Denise Show” wasn’t exactly Sandler’s most beloved bit — the skit only appeared three times during his SNL stint — but Brian’s unfiltered rage and shame informed Barry Egan, the melancholy novelty-gift proprietor who’s the unlikely protagonist of Punch-Drunk Love. Early on in the film, Barry meets Lena (Emily Watson), who like Barry operates on her own strange wavelength. Both of them a bit shy, they fall for one another, but his emotional issues — not to mention some menacing toughs trying to extort him — threaten their love affair. Bullied by his sisters, awkward around his colleagues, Barry is what Sandler’s SNL characters would be like if they existed in the real world — albeit, one in which random car crashes occur and everybody (and everything) seems slightly off. Instead of played for laughs, a Sandler character’s demons and fragility were, for once, the anxious fuel of a grownup tale about someone ill-equipped for the cruelty and senselessness of modern life. 

Anderson saw Sandler’s potential, but at times he seemed alone in that assessment. His producer JoAnne Sellar had her doubts. “I just didn’t get the whole Adam Sandler thing at that stage,” she admitted. “I mean, the Saturday Night Live stuff, yes, but the movies that Adam had done weren’t for me. As a British person I didn’t really get the humor.” Even Sandler was unsure, remembering being worried after reading the Punch-Drunk Love script. “I always said I could do this, but this was too much,” he said. “But he talked me through it, and he made me comfortable.” 

Truth is, that wariness seems baked into the performance, with Barry gingerly navigating his life as if he’s waiting for a piano to fall on his head — or, more appropriately, a harmonium, which is the instrument that finds its way into his orbit in surreal fashion early on in the film. Whether by design or because of nerves, Sandler infused Barry with a tenderness and vulnerability that was rare for him onscreen. Anderson figured out how to bring dimensions to Sandler’s onscreen persona, fleshing out the humanity without losing its endearing, inherent oddity. Ebert asked Anderson if Punch-Drunk Love was “an Adam Sandler movie or a Paul Thomas Anderson movie.” Anderson thought about it and replied, “It’s like an art-house Adam Sandler movie.” Bingo.

Perhaps not surprisingly, not many filmgoers were excited about the prospect of an art-house Adam Sandler movie. The actor’s fans wanted the supremely silly, and Anderson’s fans weren’t the kind to think that highly of Sandler’s antics. And although Punch-Drunk Love was a love story, it was an intentionally weird one — highly stylized and impressionistic, featuring an off-kilter score that seemed to replicate Barry’s shifting moods, angry flare-ups and inner anguish. It was a film that was as peculiar as Barry himself. No wonder it scared off so many people.

Today, though, Punch-Drunk Love is rightly celebrated, in part because it set the groundwork for what both men would do next. From here, Anderson would move on to other fascinatingly insular portraits of driven, troubled men, such as There Will Be Blood. As for Sandler, Punch-Drunk Love suggested what he was capable of as an actor, paving the way for his acclaimed work in Uncut Gems and Hustle. Whereas in his early career he was considered something of a lightweight — funny but maybe a bit one-note comedically — now he enjoys a cool cachet. Sure, he still makes dopey comedies, but we know at any moment he can also deliver something like Punch-Drunk Love. And Anderson recognized the possibilities before anyone else. 

Earlier this year, Sandler was asked about that film’s legacy in terms of his career growth. “I view it as something that I had an amazing time doing,” he said. “And it might have opened up other thoughts about me. I’m sure that happened. In my brain, I always thought, ‘Yeah, maybe one day, I’ll do a different style of movie.’ And luckily Paul wrote that movie, called me up said, ‘Let’s go.’”

It was all our good fortune that Sandler rose to the challenge. In Punch-Drunk Love, timid Barry has to find the courage to prove his love to Lena. Similarly, Sandler had to push himself out of his comfort zone. Both of them got their happy ending.

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