Adam Sandler<\/strong><\/a> is an industry icon for a reason. The comedic actor\u2019s decades-long career has seen him charm audiences in everything from Happy Gilmore<\/em> to The Wedding Singer <\/em>and was embraced by whole new generation of fans thanks to the animated Hotel Transylvania<\/em> franchise.<\/p>\n Sandler first gained major recognition when he became a cast member on Saturday Night Live<\/em><\/a> in 1991, a role he nabbed after initially joining the sketch series as a writer the year before. During his four-year run on the show, he created memorable characters, like Opera Man and Sleepyhead, and earned three Primetime Emmy nominations.<\/p>\n After leaving the long-running NBC show in 1995, Sandler became a bona fide movie star<\/a>. Many of Sandler\u2019s beloved flicks debuted in the late \u201890s, including the aforementioned Wedding Singer<\/em> and Happy Gilmore<\/em>. But the following decade saw him star in gems such as Punch-Drunk Love<\/em> and 50 First Dates<\/em>.<\/p>\n Though Sandler is primarily known for his comedic work, he has also proven his range in dramatic roles. Despite his status in Hollywood, not all of his films have won over film reviewers. He told the Independent<\/em><\/a> in 2013 that he is not concerned with opposing opinions.<\/p>\n \u201cI didn\u2019t get into movies to please the critics,\u201d he previously said. \u201cI got into it to make people laugh and have fun with my friends.\u201d<\/p>\n Keep scrolling to look back on Sander\u2019s best movie roles over the years:<\/p>\n Sander plays Bobby, a waterboy for a college football team. After getting fired, Bobby gets a job with a rival team and discovers he\u2019s pretty good at the sport himself. Bobby joins the team and aids them in victory.<\/p>\n As the titular character, Sander is tasked with redoing his kindergarten to high school curriculum after learning that his father paid off his teachers to help him graduate.<\/p>\n Sander plays Happy, a cranky hockey enthusiast who is actually a talented golfer. While Happy despises golf at first, he ends up competing in a tournament to help his grandmother. Nearly two decades after the comedy\u2019s release, Sander reprised his role for the sequel<\/a>, which premiered on Netflix in July 2025.<\/p>\n Like most of Sandler\u2019s roles in the \u201890s and 2000s, he stars as Sonny, a slacker who doesn\u2019t take initiative. However, his life changes after a friend\u2019s child (portrayed by Dylan<\/strong> and Cole Sprouse<\/strong>) shows up on his doorstep.<\/p>\n Sandler and Drew Barrymore<\/strong> spark instant chemistry as a wedding singer and a waitress while falling in love.<\/p>\n In the beloved rom-com, Sandler is reunited with Barrymore, whose character suffers from amnesia following a tragic car accident. Barrymore\u2019s memory resets every day, and Sandler has to win her over again and again.<\/p>\n Judd Apatow<\/strong>\u2019s 2009 flick was the perfect blend of Sandler\u2019s comedic and dramatic acting talents, as he plays a comedian battling a terminal illness.<\/p>\n Sandler received critical acclaim for his role in the dramedy as an anxious entrepreneur who falls in love with his sister\u2019s coworker.<\/p>\n\u2018The Waterboy\u2019<\/h2>\n
\u2018Billy Madison\u2019<\/h2>\n
\u2018Happy Gilmore\u2019<\/h2>\n
\n Adam Sandler in \u2018Happy Gilmore.\u2019<\/span> Universal\/Kobal\/Shutterstock<\/span><\/figcaption><\/figure>\n\u2018Big Daddy\u2019<\/h2>\n
\u2018The Wedding Singer\u2019<\/h2>\n
![\"Happy](\"https:\/\/www.usmagazine.com\/wp-content\/uploads\/2019\/09\/Adam-Sandler-Best-Movie-Roles-Over-the-Years-01.jpg?w=1000&quality=40&strip=all\")
<\/div>
\n Adam Sandler in \u2018The Wedding Singer.\u2019<\/span> New Line\/Kobal\/Shutterstock<\/span><\/figcaption><\/figure>\n\u201850 First Dates\u2019<\/h2>\n
\u2018Funny People\u2019<\/h2>\n
\u2018Punch-Drunk Love\u2019<\/h2>\n