1.) Happy Gilmore

Number one on the list is Happy Gilmore. Happy Gilmore is one of Adam Sandler’s most popular movies. Adam Sandler plays Happy Gilmore, and the plot follows an unsuccessful hockey player who becomes a successful player in golf. 

In the movie, Gilmore finds out that he can do long drives in golf when movers start moving his grandma’s furniture to a nursing home due to the fact they can’t pay off the house. The mover’s made a bet with Gilmore on who can get the longest drive, he proceeds to hit the ball over 400 yards away. 

This led to Gilmore using his skills in long drives to win money from a tour to pay off his grandma’s house. Gilmore faces many challenges in this movie, as well as opponents, and often puts everything on the line. I would rate this movie a 5/5 on the Adam Sandler scale. This movie is one of Adam’s best movies and one of his classics.

2.) Grown Ups

Ranking at number two on the list is the movie Grown Ups. This movie has many well-known actors, aside from just Adam Sandler, there is Kevin James, Chris Rock, David Spade, Rob Schneider, and Salma Hayek, along with many more popular actors in the cast. 

The main plot of the story is how five best friends who won a championship in their high school meet up with each other again after finding out about their old coach’s death. This led to them hanging out more and living their life as they did when they were kids. 

I rate this movie a 4/5. The main reason for this rating is that I could most definitely watch this movie repeatedly and not get bored of it. This movie is such a great comedy, and I really enjoy watching it. 

3.) That’s My Boy

Coming in at number three is the movie That’s My Boy. That’s My Boy is a 2012 American comedy film directed by Sean Anders, starring Adam Sandler. 

The movie follows the story of Donny Berger, a man who fathered a child with his teacher when he was only a teenager. The film is known for its crude humor and is considered one of Sandler’s most controversial roles.

Despite its mixed reviews, That’s My Boy remains a popular movie amongst Sandler fans. The movie leans more toward young adults and is rated R. I would rate this movie a 3/5. This movie is more for mature adults, but it was still pretty good. 

4.) Billy Madison

Number four on the list is the movie Billy Madison. Billy Madison is a 1995 American comedy film directed by Tamra Davis. In the movie, Billy Madison is played by Adam Sandler. Billy Madison is a man-child with no real responsibilities who is forced to go back to school to prove himself worthy of inheriting his father’s company. 

The movie is a classic of the 90s comedy genre, and it is still very popular today. The film is a great example of Sandler’s comedic style, which is characterized by juvenile humor and absurdity. Billy Madison is a must-see for fans of Sandler’s work and for anyone looking for a good laugh.

I would rate this movie a 3.5/5. My reasoning for this is because it is one of his funniest and most classic movies, although I would only watch this a few more times. 

5.) The Waterboy

Last but not least, number five on the list is The Water Boy. The WaterBoy is a 1998 American sports comedy directed by Frank Coraci, starring Adam Sandler. 

The movie follows the story of Bobby Boucher, a socially awkward water boy who becomes the star player of his college football team. The film is known for its absurd humor and over-the-top gags, and it is considered one of Sandler’s most iconic roles.

The movie is a classic of the 90s comedy genre, and it is still popular today. I’d rate this movie a 4.5/5 because it is a great comedic classic of Sandler’s. I would definitely rewatch this movie again.