Adam Sandler made his film debut in 1989, playing an aspiring comedian who takes a gig aboard a cruise ship filled with beauty queens in the little-seen Going Overboard. "All of a sudden I was in a movie! I was playing a comedian, and I didn't care about too much else in the world," Sandler recalled to Entertainment Tonight now more than 30 years later. "I was just excited about going after it."
That film wouldn't make him a movie star, but the Brooklyn-born comedian was simultaneously performing stand-up in New York City and the following year, landed his big break on Saturday Night Live. Cut to today, and his movies have grossed more than $3 billion worldwide.
Sandler has had a hand in crafting his career from the beginning: He is a writer, albeit often uncredited, on many of his projects, and nearly always an executive producer. He hand picks his directors and often casts his closest friends (Rob Schneider, David Spade and Steve Buscemi) to star alongside him. Over the years, he's gone from being one of a defining voices in comedy to one of the most fascinating dramatic actors working today, while still making time to star in the sort of broad comedies that made him famous.
"I've done both for a long time. When I went to NYU, I did a lot of scenes that were just dramatic, not funny," Sandler recently told AARP. "I like giving myself over to a new challenge. Sometimes I feel like I'm tapped out with new thoughts, and then all of a sudden, something new comes up. And I go, 'OK, how can I make this happen?' It was cool as hell pushing myself in new ways like I did on Uncut Gems... and not worrying about laughs as much as what each character is going through and pulling for. But I do love comedy more than anything."
This year, Sandler received the Mark Twain Prize for American Humor, sharing in his acceptance speech how his older brother originally inspired him to pursue acting by telling him, "'You're as funny as Rodney Dangerfield and Eddie Murphy.' I never thought that, but he made me feel like I was." His latest projects highlight his duality as a performer: Murder Mystery 2 sees him starring alongside Jennifer Aniston in another madcap comedic mystery, while he will soon reunite with Josh and Benny Safdie for a drama set in the world of sports memorabilia co-starring Megan Thee Stallion.
Below, A.frame looks back on the highlights of Sandler's decades-long career.
Sandler had already made a name for himself as a funnyman on SNL when director Michael Lehmann cast him alongside Steve Buscemi and future Oscar winner Brendan Fraser in this cult classic comedy about a rock band, The Lone Rangers, so desperate to have their music played on the radio that they hijack a radio station. Following a scene-stealing turn in 1993's Coneheads, it was Airheads that cemented Sandler's movie star potential, with Peter Travers of Rolling Stone calling him "a red-hot screen find."
Billy Madison marked Sandler's first post-SNL starring vehicle and effectively established his signature role: The Gen X man-child with a heart of gold if a juvenile sense of humor. Sandler, who also co-wrote the comedy, stars as a spoiled hotel heir whose father won't let him inherit the company unless he can prove himself by passing grades K through 12. The movie was critically panned upon its release — forever putting Sandler off reading his reviews — but is now considered a beloved entry in Sandler's oeuvre, and perhaps his most quotable movie. "Chlorophyll? More like bore-ophyll!"
Sandler and writing partner Tim Herlihy followed Billy Madison with this comedic riff on a sports movies, which casts the former as a down-and-out hockey player who discovers his skillset translates to the fairway. Carl Weather stars as Happy's mentor, Julie Bowen as his romantic interest and Christopher McDonald as a rival golfer, but it's game show host Bob Barker who runs away with the movie, making a cameo as himself and fistfighting Happy during a tournament. "The price is wrong, bitch!"
Happy Gilmore marks Sandler's first collaboration with the director Dennis Dugan, going on to make eight movies together including Big Daddy, You Don't Mess with the Zohan, Grown Ups, and 2011's Adam Sandler-in-drag-comedy Jack and Jill.
The first of Sandler's three team-ups with Drew Barrymore, The Wedding Singer casts him as a wedding singer mending a broken heart after being left at the alter and her as the waitress he falls for. The '80s-set rom-com remains the best of their collaborations, which continued with 2004's amnesia rom-com 50 First Dates and 2014's family comedy Blended. (Frank Coraci is the director behind The Wedding Singer and Blended, as well as Sandler-starrers like The Waterboy and Click.)
Paul Thomas Anderson was one of the first auteur filmmakers to capitalize on Sandler's full range in a more dramatic role — even if Sandler himself wasn't initially convinced of his own casting. PTA wrote the role of socially awkward inventor Barry Egan specifically for Sandler, tailoring the unconventional rom-com around his raw comedic energy and chemistry with Emily Watson, who plays his unlikely love interest in the film. Punch-Drunk Love earned Sandler the best reviews of his career and would foreshadow increasingly dramatic turns by the comedian.
Three-time Oscar winner James L. Brooks (Terms of Endearment) saw Sandler's performance in Punch-Drunk Love and cast him in Spanglish, which pushed him further into serio-comedic territory in a rom-com of clashing cultures. Here, he plays an unhappily married chef who strikes up a relationship with his family's maid (Paz Vega), an immigrant from Mexico hoping to give her daughter a better life.
A bit of film trivia: Sandler passed on playing Max in Michael Mann's 2004 action thriller Collateral to instead shoot Spanglish. The role of Max ultimately went to Jamie Foxx, who received an Oscar nomination for his performance in the film.
Funny People is a particularly meta entry in Sandler's filmography: Writer, director and Sandler's one-time roommate, Judd Apatow, wrote the character of George Simmons for him: A middle-aged movie star who, following a terminal diagnosis, returns to his roots of stand-up comedy. At rue Apatowian comedy, Funny People is equal parts cringey and cathartic, with Seth Rogen co-starring as an aspiring comedian that George takes under his wing and Leslie Mann as the ex-fiancée he wants to win back.
Sandler personally wrote to Noah Baumbach asking to be considered for one of the filmmaker's projects, and in turn, Baumbach wrote The Meyerowitz Stories, a dramedy about dysfunctional adult siblings played by Sandler, Ben Stiller and Elizabeth Marvel. Sandler plays the unemployed and soon-to-be divorced eldest brother, Danny Meyerowitz, as he navigates his relationship with his father (two-time Oscar winner Dustin Hoffman) and as a father (to onscreen daughter Grace Van Patten). The film marked Sandler's first to premiere at the Cannes Film Festival.
There's an alternate timeline in which Sandler never starred in Uncut Gems. As it goes, the Safdie brothers first approached Sandler to star in their drama in 2009, but Sandler's manager promptly rejected the project. Jonah Hill was instead attached to star. Thankfully, the universe righted itself and Sandler eventually signed on to play Howard Ratner, a Diamond District jeweler and gambling addict on a downward spiral of mounting debts, an estranged wife, a secret girlfriend, and the 2012 NBA playoffs. With Uncut Gems, Sandler delivered a career-best performance.
Hustle is a Sandler passion project and a tribute to one of his longtime loves: Basketball. In one of his most naturalistic and understated performances to date, Sandler stars as NBA scout Stanley Sugarman, who attempts to reboot his career after discovering a new prospect from Spain (real-life NBA player Juancho Hernangomez). Oscar nominee Queen Latifah plays Stanley's wife, with Oscar winner Robert Duvall as the owner of the 76ers. Sandler personally tapped indie filmmaker Jeremiah Zagar (We the Animals) to direct, while Lebron James served as one of the producers.