Adam Sandler has been making beloved movies for decades, and some stand out as his best work. After being a cast member on Saturday Night Live in the early 1990s, Sandler’s movie career took off with titles like Billy Madison, Happy Gilmore, and The Waterboy, establishing a slapstick humor that’s been profitable in Hollywood ever since. His films have grossed over $2 billion, from comedies to family-friendly animation to an occasional drama where Sandler reminds everyone he can seriously act.
Adam Sandler has had various hits and misses, known as one of the actors with the most Raspberry Award nominations. Still, the 57-year-old actor is a marketable figure in the industry, having recently signed a four-film deal with Netflix for $250 million in 2021. He’s earned widespread acclaim for serious, dramatic roles after starring in the Safdie Brothers’ acclaimed thriller Uncut Gems, increasing his appeal in the 2020s. He is continuously known for his humble personality off-screen despite his great success. Sandler has been in dozens of films, and while everyone has a different favorite, some are widely considered his best.
10 Big Daddy
Directed by Dennis Dugan (1999)
One of Sandler’s earliest classics is Big Daddy, where he plays the character Sonny Koufax. To prove to his ex-girlfriend that he’s capable of being responsible, Sonny adopts a 5-year-old boy, played by the Sprouse brothers, who take turns in the role due to their age. It’s a classic Sandler comedy, mixing juvenile and adult humor and ultimately having heartwarming moments. Big Daddy’s plot is relatively simple and cliché, but it is still one of his more charming, endearing earlier works.
9 Billy Madison
Directed by Tamra Davis (1995)
Billy Madison is another classic Sandler comedy, where he plays his usual man-child character. It’s a similar plot to Big Daddy, though, in this case, the titular character is a lazy adult who returns to school to prove himself to his father to take over the family business. Aside from Sandler, the film includes comedy legend Norm Macdonald. Billy Madison is praised for being one of Sandler’s most absurdly comedic movies, with his performance being a clear highlight that launched his career as a movie star.
8 Reign Over Me
Directed by Mike Bender (2007)
Adam Sandler has proven he’s a capable dramatic actor, with Reign Over Me being an early example. The film tells the story of Charlie Fineman, a man who lost his family in the September 11 attack, as he runs into his former college roommate, and the two rekindle their friendship and help each other cope with their struggles. Starring alongside Don Cheadle, Sandler is excellent in the film, mixing in his signature humor on occasion with a compelling story about grief and friendship.
7 50 First Dates
Directed by Peter Segal (2004)
Adam Sandler and Drew Barrymore’s combined star power is perfect for the feel-good comedy of 50 First Dates. Sandler plays Henry Roth, a playboy who falls for Barrymore’s Lucy Whitemore, a woman with short-term memory loss who can’t remember the previous day’s events. It’s a rom-com with a unique premise, as Henry must continue to impress Lucy each day as if it’s their first date. The film’s stars have impeccable chemistry, blending humor with heartfelt moments.
6 Hustle
Directed by Jeremiah Zagar (2022)
Adam Sandler is famously a basketball fan, and he expressed his love for the game with the Netflix movie Hustle. Sandler plays Stanley Sugerman, a scout for the Philadelphia 76ers who discovers an under-the-radar international talent named Bo Cruz. Stanley vouches for Bo, hoping to turn him into a star NBA prospect. The movie is filled with NBA player cameos, including a fantastic antagonist performance from Timberwolves All-Star Anthony Edwards. It’s one of Sandler’s best dramatic performances in a classic underdog sports movie, with the modern aesthetic of the NBA and basketball culture as its backbone.
5 Happy Gilmore
Directed by Dennis Dugan (1996)
Happy Gilmore is one of Adam Sandler’s best movies and one of the best sports comedies of all time. Sandler plays the titular character, a failed hockey player who discovers his true talents lie in golf. Gilmore enters a golf tournament in hopes of helping his grandmother keep her house, but his foul mouth and demeanor make him a natural enemy of the sophisticated golfers. Christopher McDonald’s Shooter McGavin takes a particular dislike to Gilmore, becoming the antagonist and rival of the film. Happy Gilmore is an essential Adam Sandler slapstick classic.
4 The Wedding Singer
Directed by Frank Coraci (1998)
Another Adam Sandler classic and his best comedy is 1998’s The Wedding Singer, another romantic comedy starring him and Drew Barrymore. Sandler plays wedding singer Robbie Hart, a hopeless romantic who’s been left at the altar. When brought on to help plan the wedding of Barrymore’s Julia, Robbie falls in love with her, deciding he has to win her over before she marries her wealthy jerk fiancé. The ’80s period setting of The Wedding Singer gives it a unique and fun aesthetic, and Sandler and Barrymore’s chemistry is consistently enjoyable.
3 The Meyerowitz Stories
Directed by Noah Baumbach (2017)
From Noah Baumbach (Marriage Story), The Meyerowitz Stories is an ensemble film exploring the lives of the Meyerowitz family, who meet to gather for an event. Sandler plays a dramatic role as Danny Meyerowitz alongside Ben Stiller, Dustin Hoffman, Emma Thompson, and Adam Driver. The film portrays a nuanced family dynamic, exploring the complexities of each member and their separated and interconnected experiences.
2 Punch-Drunk Love
Directed by Paul Thomas Anderson (2002)
Punch-Drunk Love can be described as a romantic comedy, but unlike much of his other work, it’s an absurd, off-beat addition to the genre. Sandler plays one of his more eccentric characters in Barry Egan, a shy business owner living a mundane life before falling for one of his sister’s co-workers, Lena. His romantic interest is made more complicated when he’s entangled in a web of extortion. It’s a unique rom-com, and Sandler gives a sensitive, nuanced performance in the classic Paul Thomas Anderson film.
1 Uncut Gems
Directed by the Safdie Brothers (2019)
Uncut Gems is one of the best A24 movies, with Sandler starring in the most powerful performance in his career. Sandler plays Howard Ratner, a jeweler and gambling addict who risks his life on a bet to pay off his debts. It’s another basketball-related film, as it also stars NBA Hall of Famer Kevin Garnett, with Radner’s bet surrounding a Boston Celtics game. Adam Sandler is exceptional in Uncut Gems, complimenting the fast-paced, intense style of the Safdie Brothers with his gripping performance, making it one of the most rewatchable Adam Sandler movies.
