ByJenika Enoch, writer at
I love movies, music, and art. I'm a certified graphic designer and love to be creative as much as humanly possible. @icemyeyes
Jenika Enoch

Adam Sandler is one of those actors that you either love or hate. Over the years it has become apparent to most that his brand of silly comedy has gotten a bit exhausting and he's lost his edge, especially with the reviews Pixels is receiving so far. However, Sandler wasn't always this bad. The films released between the mid-90's into the mid-2000's were funny and had some pretty great concepts. He proved he could carry his own films and wasn't just one of those guys you saw on Saturday Night Live for a while that just disappeared into background roles and/or writing credits.

With this list we'll focus on the top 8 Sandler films and yes, they are in order from worst to best. Just remember that because something is at the bottom of the list doesn't mean it's necessarily bad. After all, these are 8 out of the 30+ films that Sandler has starred in since 1995. Even being in last place the odds are still in their favor.

8. Little Nicky (2000)

Little Nicky was one of those that was smack in the middle of Sandler's post-90's success and it was one when you started to notice him going downhill, but he wasn't completely on the ground yet. The story followed the misfit third son of Satan, Nicky, as he's sent to Earth to retrieve his two brothers before it's too late. It has its funny moments, but for me Little Nicky was never quite on par with the rest of Sandler's work of the era.

7. Big Daddy (1999)

"Scuba Steve! Damn you!"

Personally, I love Big Daddy. It's a different concept that started testing Sandler's ability to bring more than just sex and poop jokes into his films and actually came out with a rather emotional ending. Sandler plays a lazy 30-year old who decides to fraudulently adopt a child that is dropped on his doorstep. He winds up learning the value of responsibility and caring about things that don't always directly pertain to him. It's at #7 simply because there are movies that are still better.

6. 50 First Dates (2004)

50 First Dates is an extremely sweet film with great characters. Sandler finally found his balance between comedy and emotion with this story about a man who falls in love with a woman that has short-term memory loss. It reunited him with Drew Barrymore after The Wedding Singer and it showed what a great pair the two were on screen.

5. The Waterboy (1998)

Another movie that people either love or hate, I wound up really loving The Waterboy. It's a funny character with an even funnier setting and story. Sandler plays a local university's waterboy as he's fired and quickly recruited by a rival school's team after it's discovered that he is a tackling machine. The cast was made up of some pretty respectable actors such as Kathy Bates and Henry Winkler and it had jokes that have stuck around to this day. Plus, mama taught us that everything is the devil!

4. Punch-Drunk Love (2002)

Not every great Sandler movie is a silly comedy. Many people have either forgotten about or never saw Punch-Drunk Love, but it's easily one of the best films of his career. Sandler teamed up with director Paul Thomas Anderson for this story of a mentally unstable who enters a relationship with an English woman while being extorted by a phone-sex line. It's one of those movies you really have to see to understand, but I've never met anyone who didn't like it.

3. Billy Madison (1995)

"Is that it, dad? Did the penguin tell you to do this?"

Billy Madison was the film where Sandler proved he could carry a movie on his own and have it be successful. His first leading role in the post-SNL days told the story of a rich mid-20's son of a hotel tycoon who agrees to complete 1st grade through 12th grade and re-graduate in order to take over the family company. It's crude and silly but it's truly one of the best comedies to ever come from Sandler. Truly a classic.

2. The Wedding Singer (1998)

"Now please get out of my Van Halen t-shirt before you jinx the band and they break up."

The Wedding Singer brought us back to the 1980's in style complete with David Bowie references, Miami Vice obsessions, a Boy George impersonator, and more neon colors than you can count. The first pairing of Sandler and Drew Barrymore told the adorably funny story of Robbie and Julia. After Robbie is dumped at the altar on his wedding day, his friendship with an engaged waitress named Julia escalates into something they both struggle to take the leap to grab.

1. Happy Gilmore (1996)

You just can't beat this movie. Happy Gilmore is truly Sandler's comedic masterpiece and I've never seen a film he's released that has been funnier. Sandler stars as an angry, unsuccessful hockey player who makes the switch to golf in order to earn money to keep his grandma's house from being taken by the IRS. The cast is outstanding, the jokes are even better, and the story of a man's devotion to his grandmother is sweet.

Are there any Adam Sandler films that you enjoyed that I missed? Do you think I'm wrong about Sandler's downhill slide? Leave a comment in the comments section! Just keep it respectful and clean, guys.


What's your #1 Adam Sandler movie?


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