The Greatest Movie Roles of Adam Sandler: A Must-Watch Compilation

Adam Sandler is a legendary figure in the entertainment industry for good reason. The comedic actor has delighted audiences for decades with performances in films like Happy Gilmore and The Wedding Singer, and has gained a whole new generation of fans through the animated Hotel Transylvania series.

Sandler first rose to prominence when he joined the cast of Saturday Night Live in 1991, a role that followed his initial stint as a writer on the show the previous year. Throughout his four years on the program, he introduced unforgettable characters, including Opera Man and Sleepyhead, and earned three Primetime Emmy nominations.

After departing from NBC’s iconic show in 1995, Sandler quickly became a leading man in Hollywood. Many of Sandler’s cherished films debuted in the late ’90s, including the previously mentioned The Wedding Singer and Happy Gilmore. The following decade brought standout films like Punch-Drunk Love and 50 First Dates.

While Sandler is primarily celebrated for his comedic roles, he has also showcased his versatility in dramatic performances. Despite his stature in the film industry, not all of his movies have received acclaim from critics. In a 2013 interview with the Independent, he expressed that he doesn’t let mixed reviews affect him.

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

Continue scrolling to revisit Sandler’s finest movie performances throughout the years:

‘The Waterboy’

Sandler portrays Bobby, a college football team’s waterboy who, after being fired, finds a new job with a rival team and discovers his own talent for the sport. Bobby joins the team and helps them achieve victory.

‘Billy Madison’

In the title role, Sandler must redo his education from kindergarten through high school after discovering that his father bribed his teachers to ensure his graduation.

‘Happy Gilmore’

Sandler plays Happy, an irritable hockey fan who turns out to be an exceptional golfer. Initially hating the sport, he ends up participating in a tournament to assist his grandmother. Nearly 20 years later, Sandler reprised his role for the sequel that launched on Netflix in July 2025.

‘Big Daddy’

In a classic Sandler role from the ’90s and 2000s, he stars as Sonny, a lazy man whose life takes a sudden turn when he unexpectedly becomes the guardian of a friend’s child (played by Dylan and Cole Sprouse).

‘The Wedding Singer’

Sandler and Drew Barrymore share undeniable chemistry as a wedding singer and a waitress who unexpectedly fall in love.

‘50 First Dates’

This popular romantic comedy reunites Sandler and Barrymore, whose character suffers from amnesia after an accident, forcing Sandler to win her heart anew every day.

‘Funny People’

Judd Apatow’s 2009 film perfectly merges Sandler’s comedic and dramatic skills, featuring him as a comedian dealing with a terminal illness.

‘Punch-Drunk Love’

Sandler garnered critical acclaim for his role in this dramedy as a socially anxious entrepreneur who finds love with his sister’s co-worker.

‘Spanglish’

Following his impactful performance in Punch-Drunk Love, Sandler appeared in Spanglish alongside Téa Leoni, Paz Vega, and Cloris Leachman. The film centers on Flor (Vega), who immigrates from Mexico to create a better future for her daughter, working as a housekeeper for a successful chef (Sandler) and his wife (Leoni).

‘The Meyerowitz Stories’

This film explores the lives of Sandler and Ben Stiller as estranged adult siblings navigating their father’s overshadowing legacy played by Dustin Hoffman.

‘Uncut Gems’

Sandler stars as Howard Ratner, a frantic jewelry dealer in New York City, in this thrilling drama directed by the Safdie brothers. This intense character contrasts sharply with his typical laid-back roles, showcasing Sandler’s range and skill effortlessly.