How Punch Drunk Love Changed Adam Sandler Forever

Alongside David Spade, Rob Schneider, Chris Rock, and Chris Farley, Adam Sandler became a household name during the so-called "bad boys" era of "Saturday Night Live" in the early 1990s. His mumbly antics (like a "Weekend Update" segment highlighting low-effort Halloween costumes such as "Crazy Newspaper Face") stood in sharp contrast to the more studied approach of cast members like Phil Hartman and Dana Carvey. As much as Sandler flummoxed older viewers, he was a hit with Gen-Xers and their millennial younger siblings. His first two outings on film as a comic leading man, 1995's "Billy Madison" and "Happy Gilmore" the following year, were modestly successful, setting the stage for a string of critically-reviled yet massively popular hits like "The Wedding Singer," "The Waterboy," and "Big Daddy" in the back half of the decade. 

Meanwhile, filmmaker Paul Thomas Anderson was also making a name for himself. A few years younger than Sandler, Anderson made waves with the indie gambling drama "Hard Eight" in 1996. However, his next two films, 1997's adult film saga "Boogie Nights" and 1999's everything-is-connected odyssey "Magnolia," put him on the map as one of the best directors of his generation. Few would have expected the rising star of independent cinema and the king of mainstream comedy to work together, but that's what happened with 2002's "Punch-Drunk Love." Let's look back at that most unusual romantic comedy and how it changed the trajectory of Sandler's career.

Paul Thomas Anderson was a fan of Adam Sandler for years and was particularly fascinated by his performance in a recurring "Saturday Night Live" sketch. "The Denise Show" features Sandler as a lovelorn teen hosting a talk show dedicated to his ex-girlfriend. His performance veers from mopey heartbreak to white-hot rage whenever his character's father (Phil Hartman) berates him for embarrassing the family. "Honest to God, I saw this moment where it appears the whites of his eyes turn black, and they roll back in his head," Anderson told Roger Ebert in 2002. "I would play [the sketch] back over and over again."

In a "Magnolia"-like coincidence, actress Nicole Kidman appeared in an installment of "The Denise Show" when she hosted "SNL" in 1993. Her then-husband, Tom Cruise, hung around the studio that week and became friendly with the cast, including Sandler. Years later, while filming "Magnolia," Cruise played matchmaker by calling up Sandler and putting Anderson on the phone. The young director expressed his desire to write a role for Sandler, and Sandler, not knowing Anderson or his work at that point, gave his blessing without much thought. "I said, 'You can do whatever you want, man,'" he recalled on a podcast in 2020 (via IndieWire). But when "Magnolia" came out, the prospect of doing a movie with Anderson was slightly more intimidating. "I was going, 'Oh, this guy is f**king better than me. I don't want to f**king be in this. I'm going to ruin his movie!'"

"Magnolia" is a sprawling epic about a group of disparate Angelenos and the mysterious ties that bind them. Narrated by the late actor and magician Ricky Jay and featuring an impromptu musical number set to Aimee Mann's "Save Me," the Oscar-nominated film is about as far from what Adam Sandler's Happy Madison production company was putting out at the turn of the millennium as possible. The thought of working with writer-director Paul Thomas Anderson was understandably daunting. "I was f**king scared," he told the SmartLess podcast in 2020 (via IndieWire). "I always said I could do this, but this was too much."

Anderson delivered the script for "Punch-Drunk Love" to Sandler and talked him through his hesitations. The film is much smaller in scope than "Magnolia." (No frogs are raining from the sky, for example.) And while the plot takes several unexpected turns involving an abandoned harmonium, a grocery store pudding promotion, and a phone sex scam, Sandler's character Barry Egan is in many ways a close relative to Happy Gilmore or "The Waterboy's" Bobby Boucher. With his quiet loneliness interrupted by bursts of violent rage, Barry isn't so much a departure from Sandler's comic persona as a refinement. It's as if one of those Happy Madison characters wandered off the multiplex screen and ended up in the indie drama next door. When Roger Ebert asked Anderson if he had made an Adam Sandler film or a P.T. Anderson film, he replied, "It's an arthouse Adam Sandler movie."

By 2002, Adam Sandler had built a familiar company of artists under the Happy Madison banner. He clearly liked working with the same people over and over, which quickly calcified into a Happy Madison house style. But on "Punch-Drunk Love," Sandler was in a different world with different collaborators (though Robert Smigel has a small role). Paul Thomas Anderson had his own repertory players on camera and behind the scenes, including cinematographer Robert Elswit and actors Luis Guzmán and Philip Seymour Hoffman.

Oscar-nominated actress Emily Watson was a new collaborator for Anderson and Sandler, and even 20 years later, the idea of her and Sandler working together (one a serious actor, the other decidedly not) still seems incongruous. In a SAG-AFTRA Foundation career retrospective with Watson in 2022, she gets a knowing laugh from the crowd just by saying that she prepared to work with Sandler by watching his films for the first time. However silly his screen persona was at that point, on set, he impressed Watson with his work ethic and commitment: "He is the most amazing, generous, hard-working, turns up every day, just ... really wonderful to work with." Anderson concurred, telling Roger Ebert in 2002 that he was attracted not just to Sandler's screen persona but the professional underneath. "We have a really similar work ethic. Kinda obsessed and consumed by it. And also, I wanted to learn from him about his attack on stuff. How does he make his movies? What are his concerns?"

Philip Seymour Hoffman had been a P.T. Anderson company player from the very beginning, starting as "Young Craps Player" in Anderson's debut feature, "Hard Eight." In "Punch-Drunk Love," he plays Dean, a mattress store manager in Utah, who also operates a phone sex line with a side hustle in credit card theft and extortion. Dean's intensity stands in sharp contrast to Barry's meekness; He seems to live his entire life in the kind of anger that Barry can only allow himself in extreme moments. Hoffman and Adam Sandler do not share much screen time due to their characters mostly communicating by phone, but Anderson had them on set together when filming those scenes. "I was always hearing him, and he was hearing me," Sandler said during a live Q&A for the Happy Sad Confused podcast in 2022.

The two actors had met years earlier when Hoffman auditioned for a role in "Billy Madison" — only to turn down the role after Sandler offered it to him. They became friends during the "Punch-Drunk Love" rehearsal process. "I got close with Hoff," Sandler said. "He was a really funny guy, great, strong." Hoffman's energy reminded Sandler of another close friend — His "SNL" castmate Chris Farley, who died in 1997 of a drug overdose at age 33. Unfortunately, Hoffman's similarities with Farley didn't end with a fearless intensity on stage and screen or their friendship with Sandler. Hoffman died in 2014 at age 46, also of a drug overdose.

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"Punch-Drunk Love" premiered to acclaim at the Cannes Film Festival in May 2002; Paul Thomas Anderson won best director. When the film was released in the U.S. five months later, Sandler received a Golden Globe nomination and, by far, the best reviews of his career — often begrudgingly. Veteran critic Andrew Sarris, writing in the Observer, admits in his rave review that "I have never considered myself one of Adam Sandler's greatest admirers." He goes on to praise Sandler's performance and the innate bravery of his comic persona in contrast to, oddly enough, the "tediously cowardly" persona of Bob Hope. (Take that, Bob Hope!) David Ansen affectionately dubbed the film "Unhappy Gilmore" in Newsweek, and Owen Gleiberman for Entertainment Weekly found Sandler "utterly winning" after "remov[ing] the quote marks from his famous personality."

Not every critic was wowed by the film or its central performance; Rex Reed was and remains an inveterate Sandler hater. Overall, the critical consensus was that after nearly a decade of stardom, Sandler not only had artistic ambitions but the chops to pull them off. This did not turn him into an indie darling overnight, however. After a brief, passionate affair, Sandler and the critics went back to their normal lives — he with his Happy Madison vacation-flavored comedies, they with their relentless drubbing of the same. Of Sandler's next five starring roles, four were Happy Madison productions with an average Rotten Tomatoes score in the low 40s and a combined box office gross of nearly $600 million. 

Adam Sandler's performance was a revelation — not just to critics and audiences but to other directors. In the last two decades, he has trusted his few dramatic turns to filmmakers like James L. Brooks, Jason Reitman, and Noah Baumbach. But the directors he hasn't worked with are arguably more intriguing. Writer-director Quentin Tarantino had a cameo in Sandler's 2000 Satanic comedy, "Little Nicky," and pitched the star a World War II revenge fantasy where he would play a Jewish-American soldier killing Nazis with a baseball bat. Tarantino's pitch became the 2009 film "Inglourious Basterds." The part he wrote for Sandler was Donny "The Bear Jew" Donowitz. Sadly, Sandler was committed to Judd Apatow's "Funny People," and Tarantino cast fellow director Eli Roth instead.

It's a testament to the power of Sandler's "Punch-Drunk Love" performance that it still inspires admiration from filmmakers decades later. While on the promotional tour for his 2022 classical music drama/satire (dratire?), "Tár," filmmaker Todd Field took a moment on the Happy Sad Confused podcast (via IndieWire) to gush about Sandler's turn in the 20-year-old film. "It floored me," he said. "It really is one of the great screen performances — for me — of all time." He also teased a possible collaboration at some point. "I hope we end up working together; I really do," Field said, adding, "We've been talking about some things; It's too early [to say]."

One of the most striking things about Adam Sandler's filmography post-"Punch-Drunk Love" is how few dramatic roles he has taken — only half dozen or so in two decades. It makes a certain kind of sense, though. While his comedies are reliably popular with audiences and hated by critics, his attempts at drama have been far more hit or miss over the years. Sandler's performances in James L. Brooks' family dramedy, "Spanglish," and Mike Binder's post-9/11 drama, "Reign Over Me," were well-received, but the films were stymied by sitcom plotting and unearned sentimentality, respectively. Judd Apatow's "Funny People," which cast Sandler as a movie star reevaluating his life and career after a cancer diagnosis, is at its best when exploring the world of up-and-coming comedians but, otherwise, sags under its own weight.

Despite those issues, Sandler's dramatic roles in the first decade after "Punch-Drunk Love" were largely well-received. The same cannot be said for a pair of outright disasters that hit in 2014. Jason Reitman's "Men, Women & Children" strives to be a cautionary tale about the pernicious influence of the internet and social media but winds up disjointed and borderline hysterical. However, later that year, Sandler outdid himself with "The Cobbler," Tom McCarthy's would-be fable about a shoemaker who can step into the lives of other people. Deeply misguided in nearly every way, the film becomes even more bizarre when you consider that McCarthy wrote and directed the Oscar-winning "Spotlight" just a year later.

None of Adam Sandler's dramatic roles in the 2000s through the mid-2010s earned him the same kind of acclaim he received from "Punch-Drunk Love." In 2017, he received strong notices for his role in Noah Baumbach's ensemble piece "The Meyerowitz Stories (New and Selected)," but his fortunes changed two years later with Josh and Benny Safdie's frantic character study "Uncut Gems." Sandler dominates the screen as Howard Ratner, a diamond merchant and gambler whose constant search for the next big score — symbolized by a rare and priceless opal — has alienated everyone in his life, from his wife (Idina Menzel) to his mistress (Julia Fox) and even NBA superstar Kevin Garnett (as himself). The role is an extreme departure for Sandler but also feels like a culmination of his work to that point.

Like Paul Thomas Anderson in the late 1990s, the Safdie brothers were fans of Sandler's work and wrote their script with him in mind. Sandler's manager initially rejected the script in the late 2000s, but after several years of changing hands (Jonah Hill was set to star at one point), Sandler came on board in 2018. The film was a critical success, and with $50 million at the box office, was Sandler's highest-grossing dramatic work since "Funny People." Sandler won the 2020 Film Independent Spirit Award for best male lead and, perhaps more importantly, jump-started the gold-plated Furby market.

While Adam Sandler seemed hesitant to follow up his "Punch-Drunk Love" success with more dramatic work in the early 2000s, he is wasting no time in the 2020s. He and Idina Menzel have already reunited as onscreen husband and wife in the well-received 2023 Netflix comedy "You Are So Not Invited to My Bat Mitzvah," and a new collaboration with the Safdies is already in development. Still, that begs the question: Will Sandler and Paul Thomas Anderson ever team up again?

To an extent, they already have. Sandler's 2018 stand-up special "100% Fresh" (currently 90% fresh on Rotten Tomatoes) was helmed by longtime Happy Madison director Steve Brill ("Mr. Deeds," "Hubie Halloween"), but eagle-eyed fans caught Anderson manning a camera outside the theater where the special was filmed. Anderson received a "Special Thanks" in the end credits for his efforts, though it's unclear how much of his work is in the special. Fans hoping for a more official collaboration remain disappointed. Since "100% Fresh," Sandler has kept up his breakneck pace for Netflix, churning out two "Murder Mystery" films, co-starring Jennifer Aniston, and earning strong reviews for the 2022 basketball drama "Hustle." Anderson, meanwhile, wrote and directed the '70s nostalgia piece "Licorice Pizza," starring Cooper Hoffman and musician Alana Haim in 2021, and has directed several music videos.

For an indie film that made less than $30 million at the box office, "Punch-Drunk Love" has had a remarkably long life. Looking back, Adam Sandler seems, above all, grateful for the opportunity to have made it. "It felt like a free gift from a guy who called me up and said, 'I wrote you a movie,'" Sandler told Yahoo News while promoting "Hustle" in 2022. "When that happens, it's incredible." He credits the film with breaking him out of his comfort zone and forcing him to try something new. "In my brain, I always thought, 'Yeah, maybe one day I'll do a different style of movie,'" he said in a 2022 Cinemablend interview. "And luckily, Paul wrote that movie, called me up, [and] said, 'Let's go.'"

If Sandler and Anderson never officially collaborate again, maybe that's okay. It's a well-worn internet joke that the real meaning of any given thing was "the friends we made along the way," but, in Sandler's case, that seems to be true. He is famously a gracious and generous friend, whether that means bankrolling starring vehicles for pals Kevin James and Rob Schneider or penning a poignant song about the late Chris Farley for his "100% Fresh" special. "Punch-Drunk Love" might have been an artistic breakthrough, but it was also the beginning of a decades-long friendship between Sandler and Anderson. "Paul's one of my best buddies. I love him," Sandler told Cinemablend. "So that's the greatest thing that happened with that movie."