Adam Sandler movies: 15 greatest films, ranked worst to best, include ‘Happy Gilmore,’ ‘Punch Drunk Love,’ ‘The Wedding Singer’

Adam Sandler celebrates his 52nd birthday on September 9th, so in celebration of that event, Gold Derby chooses his 15 greatest film performances.

Like many popular comedic actors of the day, Sandler got his start on “Saturday Night Live” first as a writer and then as a cast member. He was spotted by weekend update anchor Dennis Miller doing stand-up comedy and Miller recommended him for the show. Sandler was a big success on the show, particularly doing song parodies during the Weekend Update segments. Sandler left the show in 1995 after only five years on the program. Years later when Conan O’Brien was having his own problems with NBC, Sandler admitted to O’Brien that he was actually fired from “SNL” and didn’t leave voluntarily as had been assumed.

Sandler started off doing comedy films after that but has evolved into doing dramatic work at times. While he has a pretty strong track record as a box office draw, he has also often been the target of poor reviews from critics and has frequently been singled out by the Razzies.

Let’s take a photo gallery tour of his movies, ranked from worst to best. Our list includes “Happy Gilmore,” “Billy Madison,” “Punch-Drunk Love,” “The Wedding Singer,” “The Waterboy” and more.

Sandler plays a hotel handyman who likes to make up stories for his niece and nephew. The stories start coming true in this fantasy film from Walt Disney.

Sandler plays an Israeli soldier who fakes his own death in order to move to the US. He takes up work as a hair dresser but can’t seem to escape his military past.

13. MR. DEEDS (2002)
Sandler plays a quiet, unassuming small-town aspiring greeting card writer who suddenly finds himself in charge of a huge media corporation after a relative dies.

This film is the story of how a bunch of prison inmates challenge their prison guards to a football game. It is a remake of a highly successful film from the 1970s starring Burt Reynolds, who also appears in this version.

11. 50 FIRST DATES (2004)
Sandler finds the girl of his dreams but unfortunately, she has no short-term memory so everyone of their dates is a first date.

10. BIG DADDY (1999)
Sandler plays the ultimate slacker who finally grows up after he is forced to take care of an abandoned child. Despite having graduated from law school he works as toll booth collector but through the child he eventually figures out his life.

9. THE WATERBOY (1998)
Sandler shocked box office pundits when very early in his career this comedy opened in first place at the box office. Sandler plays a waterboy for a college football team who gets a chance to join the team.

In this popular comedy Sandler has to go back to school and complete all 12 grades in order to prove to his father that he is capable of running his company.

Sandler teamed with Jack Nicholson for this comedy about two men whose temper gets them in trouble. The two decide to face the problem and learn to control their rage.

6. SPANGLISH (2004)
James L. Brooks won three Oscars for “Terms of Endearment” and produced “The Mary Tyler Moore Show,” but this movie is a long way from those days. He wrote and directed this story of a Mexican immigrant and her daughter who go to work for a wealthy family. Cloris Leachman reunited with Brooks here and earned a SAG nomination as Best Supporting Actress.

Sandler plays an aspiring hockey player in this early comedy of his. It is probably best remembered for a scene where Bob Barker plays himself and gets into a fight with Sandler on a golf course.

Highly successful at the box office, this film features Sandler as a singer who is in love with one woman but engaged to another.

3. REIGN OVER ME (2007)
Sandler took on a dramatic role as a man who lost his family in the terrorist attacks on 9/11. He has trouble maintaining his sanity and dealing with his grief but finds relief in a chance meeting with his old college roommate.

Sandler joined a strong ensemble cast in this dark comedy from writer director Noah Baumbach.

Sandler earned a Golden Globe Nomination for his mostly comedic role for this film from writer director Paul Thomas Anderson. Sandler plays a man tormented by work and family pressures.

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