Adam Sandler is a unique Hollywood star. Starting as a standout writer and performer on Saturday Night Live, he quickly transitioned into a box office juggernaut who dominated the comedy landscape of the 1990s and early 2000s. His early work established a specific brand of humor rooted in surreal outbursts and an unapologetic embrace of the absurd. While critics often dismissed these initial efforts as lowbrow, audiences responded to the genuine heart that beat beneath the silly voices and slapstick violence. Over the decades, Sandler’s production company, Happy Madison, became a factory for hits that allowed him to work alongside his closest friends while consistently delivering entertainment that resonated with the masses.
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However, reducing Sandler to just his comedic output ignores the incredible dramatic range he has displayed throughout his career. Every few years, he steps away from the comfortable formula of his comedies to deliver a performance that leaves audiences and critics stunned by his depth and vulnerability. Furthermore, Sandler worked with some of the most respected auteurs in cinema, proving that the guy who sang about a red hooded sweatshirt is also capable of anchoring character studies. This duality makes his filmography one of the most interesting to explore, as it oscillates between comfort-food cinema and high-anxiety drama.
10) The Waterboy
Sports comedies were a staple of the late 1990s, and The Waterboy stands as one of the most commercially successful examples of the genre. The film stars Sandler as Bobby Boucher, a socially stunted water boy who discovers he has a unique talent for tackling people with devastating force. He joins the South Central Louisiana State University Mud Dogs, a team led by the eccentric Coach Klein (Henry Winkler), and attempts to lead them to the Bourbon Bowl. While the plot is standard underdog fare, the movie succeeds because of the committed performance from the lead and the hilarious supporting turn by Kathy Bates as his overprotective Mama. It features some of the most quotable lines in the Sandler canon and embraces a cartoonish energy that makes the bone-crunching football hits feel genuinely funny rather than violent. The Waterboy captures Sandler at the height of his slapstick powers, delivering a character that is impossible to take seriously yet easy to root for.
9) 50 First Dates
Reuniting with a co-star often yields diminishing returns, but 50 First Dates proved that the chemistry between Sandler and Drew Barrymore was no fluke. In the movie, Sandler plays Henry Roth, a veterinarian in Hawaii who falls for Lucy Whitmore (Drew Barrymore), only to discover she suffers from Goldfield’s Syndrome, a fictional form of anterograde amnesia that resets her memory every morning. Instead of giving up, Henry decides to win her over every single day, leading to a series of creative and touching romantic gestures. The film balances the humor of Henry’s predicament with the genuine tragedy of Lucy’s condition, creating a rom-com that feels emotionally grounded despite its high-concept premise. In addition, Sandler steps back from his usual manic energy to play a charming lead, allowing the romance to take center stage. The ending also avoids a magical cure in favor of a realistic resolution, making it one of the most mature stories in the Happy Madison library.
8) Big Daddy
Transitioning from college humor to stories about responsibility was a necessary step for Sandler, and Big Daddy served as the perfect bridge between those two eras. He plays Sonny Koufax, a slacker law school graduate who adopts a five-year-old boy named Julian (Dylan and Cole Sprouse) to impress his girlfriend. When the girlfriend dumps him, Sonny is stuck raising the kid, eventually learning that there is more to life than delivering food and rollerblading. The movie strikes a chord because it allows Sandler to retain his rebellious edge while interacting with a child who mimics his bad behavior. It creates a dynamic that is both hilarious and surprisingly sweet, especially as Sonny fights the legal system to keep custody of the boy. Big Daddy showed audiences that the comedian could handle emotional beats without losing the juvenile charm that made him famous, which is why it’s one of Sandler’s best movies.
7) Hustle
Netflix has served as the home for many of Sandler’s lower-effort comedies, but Hustle stands out as a genuine sports drama that respects the game of basketball. This time around, Sandler stars as Stanley Sugarman, a weary scout for the Philadelphia 76ers who discovers an incredible talent named Bo Cruz (Juancho Hernangómez) playing in a street game in Spain. Stanley risks his career to bring Bo to the United States, training him for the NBA draft while battling the skepticism of the team’s owner (Ben Foster). The film avoids the cynicism of the industry to focus on the love of the sport, featuring cameos from countless real-life NBA stars that lend the project authenticity. Sandler disappears into the role of Stanley, portraying a man who is exhausted but driven by a pure passion for the game, turning Hustle into an inspirational story that charmed audiences and critics alike.
6) The Meyerowitz Stories (New and Selected)
Director Noah Baumbach is known for his sharp dialogue and dysfunctional family dynamics, and he found a perfect muse in Sandler for The Meyerowitz Stories (New and Selected). The film revolves around the children of Harold Meyerowitz (Dustin Hoffman), an artistic patriarch who casts a long shadow over his offspring. Sandler plays Danny, the eldest son who has always felt neglected in favor of his more successful half-brother Matthew (Ben Stiller). Sandler’s acting is understated and raw, capturing the specific pain of a man who desperately wants approval from a father incapable of giving it. Plus, the actor holds his own against dramatic heavyweights like Hoffman and Emma Thompson, delivering a performance that conveys a lifetime of insecurity. The Meyerowitz Stories is a film that highlights Sandler’s ability to play broken men with a level of nuance that his comedies rarely allow.
5) Billy Madison
Every legend has a beginning, and Billy Madison is the film that solidified the Sandler persona for an entire generation. In the movie, he plays the titular character, the heir to a hotel fortune who must repeat grades 1 through 12 in 24 weeks to prove he is competent enough to run the company. The premise is completely absurd, providing a blank canvas for surreal gags involving a giant penguin, a menacing bus driver (Chris Farley), and a musical number about passing the third grade. Critics at the time were baffled by the film’s lack of logic, but it became a cult classic because of its anarchic spirit. Billy Madison is pure id, featuring a lead performance that is equal parts charming and obnoxious. It established the template for the man-child character that Sandler would refine over the next decade.
4) Happy Gilmore
Building on the success of his previous hit, Happy Gilmore took the aggressive persona of Billy Madison and gave it a clear target: the snobbish world of professional golf. Sandler stars as a failed hockey player who discovers he can drive a golf ball 400 yards, a skill he uses to join the PGA tour to save his grandmother’s house. The movie works because it pits the blue-collar, rage-filled Happy against the ultimate villain, Shooter McGavin (Christopher McDonald). The conflict between Happy’s rough demeanor and the etiquette of the golf course provides endless comedic momentum. Furthermore, the film features one of the greatest cameos in cinema history when Happy gets into a fistfight with game show host Bob Barker. Happy Gilmore remains one of the best of Sandler’s comedies, balancing aggression and heart in a way he has never quite replicated.
3) The Wedding Singer
Set against the neon backdrop of the 1980s, The Wedding Singer is the film that proved Adam Sandler could be a legitimate romantic lead. The movie revolves around Robbie Hart (Sandler), a nice-guy wedding singer who gets left at the altar and spirals into a depression that ruins his gigs. He eventually finds solace with Julia Sullivan (Drew Barrymore), a waitress engaged to a cheating businessman. The film relies heavily on 80s nostalgia, but the emotional core is timeless. In addition, Sandler uses his musical talents to great effect, performing original songs like “Grow Old With You” that are genuinely touching. The Wedding Singer is a sweet, sincere movie that toned down the aggression of Sandler’s previous characters to reveal a vulnerability that audiences instantly fell in love with.
2) Punch-Drunk Love
Director Paul Thomas Anderson saw something in Adam Sandler that no one else did, and the result was the anxiety-inducing masterpiece Punch-Drunk Love. The story follows Sandler as Barry Egan, a lonely novelty toilet plunger salesman who is constantly berated by his seven overbearing sisters. When he meets a woman named Lena Leonard (Emily Watson), he finds a reason to stand up for himself, even as he gets entangled in an extortion plot run by a mattress salesman (Philip Seymour Hoffman). Anderson utilizes Sandler’s pent-up rage to depict a man on the verge of a psychological breakdown. The performance is terrifying and tragic, stripping away the safety net of comedy to show the real-world consequences of repressed anger. Punch-Drunk Love recontextualized Sandler’s entire career, proving that his specific set of skills could be used to create high art.
1) Uncut Gems
Decades into his career, Adam Sandler delivered the best performance of his life in the Safdie brothers’ nerve-shredding thriller Uncut Gems. He stars as Howard Ratner, a chaotic New York City jeweler with a gambling addiction who bets everything on the sale of a rare black opal. The film is a relentless assault on the senses, trapping the viewer in Howard’s frantic world as he juggles loan sharks, a mistress, and angry basketball stars. Sandler is magnetic in the role, playing a character who is objectively unlikable yet undeniably compelling. He infuses Howard with a desperate optimism, a belief that the big win is always just around the corner, offering a kinetic energy that anchors one of the most stressful movies ever made. Uncut Gems stands at the top of this list because it utilizes every aspect of Sandler’s talent to create a tragic figure for the ages.
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