Adam Sandler has built up enough good will in the entertainment industry that he’s never faced a serious reckoning his lackluster material. Unlike other former Saturday Night Live stars like Bill Murray and Eddie Murphy, whose success easily translated to the big screen, Sandler never had critics on his side. Early Sandler films like Billy Madison and The Waterboy were seen as pandering, lowest-common denominator humor. They represented a type of PG-13 film that could still appeal to eight-year-olds, yet didn’t show any effort to hide their blatant product placement and derivative narrative beats. Despite the fact that he consistently raked in millions at the global box office, Sandler was still able to position himself as an “underdog” due to the scathing reviews he received from mainstream critics.
The 1990s saw many of its comedy stars take on more ambitious work. It wasn’t long after It’s Something About Mary that Ben Stiller proved to be an excellent filmmaker, as he’s now directed one of the decade’s best new shows with Severance; similarly, Jim Carrey cashed in on the massive paychecks for Dumb and Dumber and Liar Liar through collaborations with filmmakers like Milos Forman, Frank Darabont, and Michel Gondry. Sandler’s flirtation with prestige was seemingly accidental; Paul Thomas Anderson cast him as the lead in Punch-Drunk Love after he was a fan of Sandler’s Razzie-nominated 1999 comedy Big Daddy.
The irony of Sandler’s excellent performance in Punch-Drunk Love is that it’s not much different from the type of petulant, underappreciated man-children he has played in the past. The absurdism that Anderson’s style allowed for doesn’t disguise the fact that Punch-Drunk Love is a straightforward romantic comedy that maximized Sandler’s impact. Anderson realized that the nasty, loud-mouthed persona Sandler had begun to craft in Little Nicky and Anger Management would have a short shelf-life; Sandler is better at playing a sweetheart, which is why The Wedding Singer is the only one of his 1990s films that’s held up. Punch-Drunk Love is an anxiety-inducing adventure within the life of an unlucky man who has a heart of gold, and Sandler’s Barry Egan became a character worth rooting for.
Punch-Drunk Love freed Sandler from his loyalty to fellow collaborators at Happy Madison, the production company he founded in 1999. Sandler offered roles to his longtime friends Rob Schneider and David Spade in nearly all of his self-produced comedies, which made them feel like an inside joke that the audience was completely oblivious to.
Sandler’s next few years were filled with projects that fell just short of being elevated. Spanglish may have been directed by James L. Brooks, but it hardly had the same wit or whimsy as Broadcast News or Terms of Endearment. Similarly, The Longest Yard was a futile attempt to remake the 1974 sports classic that contained none of the grittiness or anti-establishment sentiments that had made Robert Aldrich’s original a defining film of the New Hollywood era.
While Sandler’s bizarre Israeli propaganda film You Don’t Mess with the Zohan is hardly a masterpiece, it at least allowed Sandler to physically transform to play a character. In one of the savviest business moves that any Hollywood A-lister has ever made, Sandler chose to sidestep disputes about the profitability of his films when he signed an overall deal with Netflix in 2014. Although the company has claimed that Sandler comedies like The Ridiculous 6, The Do-Over, Sandy Wexler, and The Week Of are among the most streamed films of all-time, there’s little evidence to suggest that they actually exist.
If Sandler’s willingness to sacrifice the theatrical market seemed to confirm accusations that he had sold out, then he immediately silenced doubters about his acting ability by giving two of the best performances of his career. Within the barrage of Sandler’s Netflix originals was The Meyerowitz Stories, a tale of a dysfunctional family of New York artists from Noah Baumbach, the writer/director behind The Squid and the Whale and Frances Ha. Although Baumbach is often seen as the modern equivalent of Woody Allen, The Meyerowitz Stories is freed from pretensions, as it showed how childhood insecurities tend to linger long into adulthood. It’s a film where Sandler could angrily shout at traffic and still be as funny, but also an opportunity for him to go toe-to-toe with Dustin Hoffman in a nakedly emotional confrontation.
If The Meyerowitz Stories was overlooked in the award conversation, Sandler proved his arthouse credentials when Uncut Gems became one of the highest-grossing films in the history of A24. Sandler hadn’t chosen to work with an established auteur, as Josh and Benny Safdie had made a series of under-the-radar independent thrillers with cynical, nasty sensibilities. In the character of Howard Ratner, Sandler created a modern anti-hero worthy of Travis Bickle from Taxi Driver or Patrick Bateman in American Psycho; Sandler’s character was impossible to look away from.
Sandler followed up Uncut Gems with another round of generic Netflix flicks, even if he worked in another solid performance in the sports drama Hustle. This year, Sandler has been floated as a potential Oscar contender for the upcoming Netflix dramedy Jay Kelly, which is a reunion with Baumbach. Whether or not it’s a success is superfluous to Sandler, as he still has Happy Gilmore 2 to line his bank account.
