From his early days as a lovable man-child to his more recent turns as a serious, award-contending actor, Sandler has forged a unique path in Hollywood. He’s a star whose name is a genre in itself, and whose influence on comedy is undeniable.
As we celebrate his 59th birthday, we look back at 10 iconic roles that not only cemented his legacy but also charted the remarkable evolution of his career.
Billy Madison (1995)
IMDb
In this film, Sandler plays the titular Billy, a wealthy slacker and an immature heir to his father’s hotel fortune. To prove he’s worthy of inheriting the family business, Billy must go back to school and re-do all 12 grades in just 24 weeks. The film’s absurd premise, loud humor, and Sandler’s unapologetic embrace of his man-child persona became his comedic blueprint. This role was crucial as it served as his first major feature film and established the distinct comedic style that would define his wildly successful run of ’90s comedies.
Happy Gilmore (1996)
IMDb / Photos/Getty Images Courtesy
Sandler starred as Happy Gilmore, a boorish, hot-tempered hockey player who, after discovering his powerful slap shot is perfect for golf, joins the PGA tour to save his grandmother’s home from foreclosure. His unconventional methods and constant clashes with a snooty rival made for a chaotic and hilarious sports comedy. Its massive commercial success cemented him as a bankable Hollywood star who could carry a film on the strength of his comedic appeal alone.
The Wedding Singer (1998)
IMDb
In a notable shift from his previous slapstick comedies, Sandler played Robbie Hart, a wedding singer who, after being left at the altar, falls for a charming waitress named Julia (Drew Barrymore). The film is a romantic comedy that blends his signature humor with a sweet, nostalgic ’80s aesthetic. This role was a turning point for Sandler, proving his ability to be a romantic lead and showcasing a softer, more endearing side to his acting. The film was both a critical and commercial success, launching his beloved on-screen partnership with Drew Barrymore.
The Waterboy (1998)
IMDb / Getty Images
Sandler’s character, Bobby Boucher, is a socially inept and stuttering 31-year-old waterboy for a college football team. When he discovers he has a talent for tackling, he becomes a star player, all while fighting for the respect of his mother and his team. This role was a huge box office hit and a return to his brand of exaggerated, character-driven comedy.
Big Daddy (1999)
IMDb
In this heartfelt comedy, Sandler plays Sonny Koufax, a lazy law school graduate who adopts a young boy (played by Dylan and Cole Sprouse) to impress his girlfriend. As he becomes the child’s unconventional father, Sonny learns about responsibility and love in a chaotic, hilarious way. The film was a major commercial hit, grossing over $234 million worldwide. This role was a significant step in his career, as it showcased his ability to blend his signature comedy with a warmer, more emotional core, setting the stage for his later family-friendly hits.
Punch-Drunk Love (2002)
IMDb
In this independent romantic comedy-drama, Sandler delivered a stunning, against-type performance as Barry Egan, a man with social anxiety and explosive rage who falls in love while dealing with a bizarre phone-sex scam. Director Paul Thomas Anderson took a risk on Sandler, and the result was a critical triumph. The role earned Sandler his first Golden Globe nomination and proved to the world, and himself, that he was capable of profound dramatic acting.
50 First Dates (2004)
IMDb
Reuniting with Drew Barrymore, Sandler starred as Henry Roth, a veterinarian in Hawaii who falls for an art teacher named Lucy who suffers from short-term memory loss. He must find new and creative ways to make her fall in love with him all over again every single day. This romantic comedy was a massive commercial success, grossing over $198 million worldwide. The film’s success re-established his place as a romantic leading man and cemented his status as a reliable box office draw.
Reign Over Me (2007)
IMDb
In a dramatic departure from his usual roles, Sandler plays Charlie Fineman, a man suffering from post-traumatic stress disorder after losing his family in the 9/11 attacks. He reconnects with his old college roommate and begins a journey to deal with his grief. His subtle and moving performance earned him widespread critical acclaim. This role was pivotal in showcasing his versatility, as he proved he could handle a sensitive and emotionally complex subject with great depth and empathy.
Uncut Gems (2019)
IMDb
Sandler delivered a career-defining performance as Howard Ratner, a charismatic but self-destructive jeweler and gambling addict in New York’s diamond district. The film is a nerve-shredding thriller that follows Howard as he makes a series of high-stakes bets that could either make him a fortune or destroy his life. The role was a critical sensation, earning him numerous accolades from the National Board of Review and the New York Film Critics Circle.
Hustle (2022)
IMDb
In this sports drama, Sandler played Stanley Sugerman, a down-on-his-luck basketball scout who discovers a raw talent in Spain and tries to get him a spot in the NBA. This role was another major success for Sandler, earning him critical acclaim for his raw and compelling performance as a man chasing his last chance. The film, which was released on Netflix, proved that Sandler’s brand of dramatic storytelling could thrive on streaming services and connect with a massive global audience.
A Studio Built on Friendship and Family
A defining hallmark of Adam Sandler’s career is his unwavering loyalty to a core group of friends and fellow Saturday Night Live alumni. This inner circle includes frequent collaborators like Rob Schneider, David Spade, Chris Rock, Kevin James, and Steve Buscemi. By consistently casting his friends in his films, Sandler has cultivated a unique, informal, and collaborative atmosphere on set.
Adam Sandler’s loyalty extends even further, making his films a true family affair. He met his wife, Jackie Titone Sandler, on the set of Big Daddy in 1999, and they have been inseparable ever since, both personally and professionally. Jackie has since become a recurring face in almost all of his films, often appearing in small but memorable roles. Now even their daughters appear in his movies, continuing an endearing tradition for fans to spot. This trend is a powerful testament to the central role his family and friends play in both his personal life and his work.
