Adam Sandler Is the King of Comedy: Look Back on His Best Movie Roles Over the Years

Adam Sandler is an industry icon for a reason. The comedic actor’s decades-long career has seen him charm audiences in everything from Happy Gilmore to The Wedding Singer and was embraced by whole new generation of fans thanks to the animated Hotel Transylvania franchise.

Sandler first gained major recognition when he became a cast member on Saturday Night Live 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.

After leaving the long-running NBC show in 1995, Sandler became a bona fide movie star. Many of Sandler’s beloved flicks debuted in the late ‘90s, including the aforementioned Wedding Singer and Happy Gilmore. But the following decade saw him star in gems such as Punch-Drunk Love and 50 First Dates.

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 in 2013 that he is not concerned with opposing opinions.

“I didn’t get into movies to please the critics,” he previously said. “I got into it to make people laugh and have fun with my friends.”

Keep scrolling to look back on Sander’s best movie roles over the years:

‘The Waterboy’

Sander plays Bobby, a waterboy for a college football team. After getting fired, Bobby gets a job with a rival team and discovers he’s pretty good at the sport himself. Bobby joins the team and aids them in victory.

‘Billy Madison’

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.

‘Happy Gilmore’

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’s release, Sander reprised his role for the sequel, which premiered on Netflix in July 2025.

‘Big Daddy’

Like most of Sandler’s roles in the ‘90s and 2000s, he stars as Sonny, a slacker who doesn’t take initiative. However, his life changes after a friend’s child (portrayed by Dylan and Cole Sprouse) shows up on his doorstep.

‘The Wedding Singer’

Sandler and Drew Barrymore spark instant chemistry as a wedding singer and a waitress while falling in love.

‘50 First Dates’

In the beloved rom-com, Sandler is reunited with Barrymore, whose character suffers from amnesia following a tragic car accident. Barrymore’s memory resets every day, and Sandler has to win her over again and again.

‘Funny People’

Judd Apatow’s 2009 flick was the perfect blend of Sandler’s comedic and dramatic acting talents, as he plays a comedian battling a terminal illness.

‘Punch-Drunk Love’

Sandler received critical acclaim for his role in the dramedy as an anxious entrepreneur who falls in love with his sister’s coworker.

‘Spanglish’

Following his role in Punch-Drunk Love, Sandler was cast in Spanglish alongside Téa Leoni, Paz Vega and Cloris Leachman. The film tells the story of Flor (Vega) as she immigrates from Mexico to give her daughter a better life. Flor gets a job as a housekeeper for a successful chef (Sandler) and his wife, played by Leoni.

‘The Meyerowitz Stories’

The film follows Sandler and Ben Stiller as dysfunctional adult siblings trying to live in the shadow of their father, played by Dustin Hoffman.

‘Uncut Gems’

Sandler starred as Howard Ratner — an anxiety-ridden jewelry dealer in New York City — in the Safdie brothers-directed crime thriller. The manic character was a change of pace for Sandler, who is known for his laid back roles, but the actor tackled the challenge with ease.