10
The Longest Yard (2005)
The Longest Yard (2005)

In this sports comedy remake, Sandler plays a former NFL quarterback who leads a team of inmates in a football game against prison guards. The film combines humor with action, showcasing his versatility.

 


IMDb

6.4/10

Rotten Tomatoes

32%

Amazon

4.8/5

“Careful, that’s my throwing arm.”

9
50 First Dates (2004)
50 First Dates (2004)

Reuniting with Drew Barrymore, Sandler portrays a man who falls in love with a woman suffering from short-term memory loss. The film blends comedy with romance, highlighting his continued appeal in heartfelt roles.

 


IMDb

6.8/10

Rotten Tomatoes

45%

Amazon

4.7/5

“Can I have one last first kiss?”

8
Anger Management (2003)
Anger Management (2003)

Starring alongside Jack Nicholson, Sandler plays a mild-mannered man who is wrongly sentenced to an anger management program. The film’s success further established his ability to hold his own with veteran actors.

 


IMDb

6.3/10

Rotten Tomatoes

42%

Amazon

4.6/5

“You can’t treat people this way and get away with it!”

7
Punch-Drunk Love (2002)
Punch-Drunk Love (2002)

Departing from his typical comedic roles, Sandler delivers a critically acclaimed performance as a lonely businessman dealing with personal and professional turmoil. The film showcased his range and earned him widespread praise.

 


IMDb

7.3/10

Rotten Tomatoes

79%

Amazon

4.7/5

“I have a love in my life. It makes me stronger than anything you can imagine.”

 


IMDb

6.3/10

Rotten Tomatoes

42%

Amazon

4.6/5
6
Mr. Deeds (2002)
Mr. Deeds (2002)

In this remake of the classic film, Sandler portrays a small-town man who inherits a massive fortune. The movie marked a significant moment in his career, blending his comedic roots with a more mature storyline.

“I fear you are underestimating the sneakiness, sir.”

 


IMDb

5.8/10

Rotten Tomatoes

22%

Amazon

4.7/5
5
Big Daddy (1999)
Big Daddy (1999)

Playing a man who adopts a child to impress his ex-girlfriend, Sandler balances comedy with moments of genuine emotion. The film’s success demonstrated his versatility and ability to lead box office hits.

“You can do it!”

 


IMDb

6.4/10

Rotten Tomatoes

39%

Amazon

4.6/5
4
The Waterboy (1998)
The Waterboy (1998)

Sandler takes on the role of a socially awkward waterboy who becomes a college football star. The film was a commercial success, highlighting his knack for creating endearing, offbeat characters.

“Mama says alligators are ornery because they got all them teeth and no toothbrush.”

 


IMDb

6.2/10

Rotten Tomatoes

33%

Amazon

4.8/5
3
The Wedding Singer (1998)
The Wedding Singer (1998)

In this romantic comedy set in the 1980s, Sandler plays a wedding singer who falls for a waitress, played by Drew Barrymore. The film showcased his ability to blend humor with heartfelt moments, expanding his appeal to a broader audience.

“I want to grow old with you.”

 


IMDb

6.9/10

Rotten Tomatoes

72%

Amazon

4.8/5
2
Happy Gilmore (1996)
Happy Gilmore (1996)

Portraying a failed hockey player who discovers a talent for golf, Sandler delivers a performance filled with his signature humor and energy. The film’s success further solidified his place in the comedy genre.

“The price is wrong, Bob!”

 


IMDb

7.0/10

Rotten Tomatoes

63%

Amazon

4.8/5
1
Billy Madison (1995)
Billy Madison (1995)

Sandler stars as a spoiled man-child who must repeat grades 1–12 to inherit his father’s company. This film marked his breakout role, showcasing his unique comedic style and establishing him as a leading man in Hollywood.

“Back to school, back to school, to prove to Dad that I’m not a fool.”

 


IMDb

6.4/10

Rotten Tomatoes

41%

Amazon

4.7/5

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