Ever since four year old me was blown away by the utterly awesome and wildly entertaining Hotel Transylvania franchise, I have been a huge fan of Adam Sandler's work in the comedy genre. When I discovered Paul Blart: Mall Cop in the sixth grade and later Pixels, which eventually became one of my all time favorite movies, I grew obsessed with Happy Madison and today, in 2022, I have seen over 20 of Adam Sandler's movies and enjoyed all of them. However, out of all the ones I've seen, there are quite a few that stand out, and those are the ones I'll be ranking best to worst in this epic blog post!!!
10 - Grown-Ups 2 (2013)
I may be in the minority here, but I strongly prefer this film over the first one. While it may not be the best Adam Sandler movie ever made, Grown-Ups 2 is a really fun movie far more enjoyable than the original, even if Rob Schneider isn't in it. This movie tells a really epic story about a bunch of childhood friends now in middle age wanting to do what's best for their families, but in the meantime they need to prove themselves still cool and more epic than all the frat boys who find themselves superior.
This movie is full of a wide cast of hilarious characters, and the friendship dynamic between Adam Sandler, Kevin James, Chris Rock and David Spade is very entertaining. The potty humor had me dying of laughter, the final battle at Lenny's '80s party was hilarious, and a few of the main characters underwent okay arcs so yeah, this is a pretty fun Sandler movie.
9 - Billy Madison (1995)
Basically to Adam Sandler movies as the original Iron Man is to the MCU. This was the Sandler classic that started it all. As a very re-watchable brilliantly hilarious movie, Billy Madison was the first along a long line of movies that let Adam Sandler just do crazy improv stuff in front of the camera and thank god it did because it was awesome. All the lines about shampoo being better than conditioner or "Mister Penguin" crack me up just thinking about them!
The movie had a really good cast as well, featuring the awesome Steve Buscemi scene with E.L.O.'s Telephone Line, Chris Farley's iconic performance as the bus driver and Billy's hilarious friend Frank who's played by the late Norm Macdonald. Soundtrack was absolutely stacked, and the message of using intelligence if you have it was really positive I felt. Billy Madison in general is an overall pretty awesome movie.
8 - Happy Gilmore (1996)
It's practically impossible not to put this on my list. I mean, c'mon, it's Happy freakin' Gilmore for crying out loud! This is definitely one of Adam Sandler's best comedic performances, since his character Happy had a very solid arc. Not only was it incredibly awesome whenever Happy would get into a fight with someone but in general, he learned a very positive and relatable message about cooling down when you get mad and trying a sophisticated approach to sports.
There are a lot of awesome supporting characters in this movie as well, such as Carl Weathers as his mentor Chubs Peterson, Ben Stiller as the insanely hilarious Hal L. and countless more characters that help make the movie entertaining. As the first film on this list focusing more on good story than on laughs and comedic value, Happy Gilmore revolutionized the Sandlerverse and is hands down one of the greatest comedies ever made.
7 - Hubie Halloween (2020)
Absolutely brilliant movie. I love it so much. So many parts of it make me die laughing, such as Steve Buscemi as the werewolf, the farmers mourning the pig Peanut's death, Kevin James' lies about the AUU, Shaquille O'Neal's ridiculous and unexpected "radio voice", pretty much anything involving the Swiss Army Thermos and more. This also has pretty a-game cinematography as far as goofy comedies go, but that isn't the entirety of what makes this movie so awesome.
The story of Adam Sandler's character, Hubie Dubois, teaches a very good positive message that stands out as one of the best on this list. Hubie's been picked on, bullied and ridiculed his entire life, but how does he react to the abuse? With kindness, and even though he's a scaredy-cat he's a good person because to quote Hubie's mom "true bravery is being kind to other's, even when they're being cruel to you". This is arguably the best and most meaningful message you'll get from a Happy Madison film, and it's helped me rethink my approach on life to this day so yeah, for loads of reasons, Hubie Halloween is one of the best Sandler movies.
6 - Little Nicky (2000)
Totally crazy, out of control but magnificent devil comedy that comes to be one of the wackiest films in comedy history. Just the pure weird insanity of it - a talking bulldog, a wimpy Satan-spawn who can only go so evil to the risk of turning his roommate's Coke into Pepsei and Ozzy Osborn randomly showing up at the climax to bite the bad guys head off - is a lot of what makes it stand out from other Adam Sandler movies and easily lands it just outside of my top five.
The movie introduced the concept of all of Sandler's movies being in the same universe by re-using characters such as Towney from The Waterboy, Chubs Peterson from Happy Gilmore and Jimmie Moore from The Wedding Singer, and there's barely been a single Happy Madison movie since then without some sort of reference to one of Sandler's older classics. Little Nicky taught a good message about being yourself no matter where you belong and it's all around very enjoyable as well as brave.
5 - 50 First Dates (2004)
Excellent rom-com with amazing story and clever humor. Adam Sandler's character, Henry Roth, is potentially my all time favorite character of his because his arc is so amazing. Roth starts out as a hunky stud in Hawaii who can't even commit to a girl for more than one night, but when he meets Lucy (Drew Barrymore), a girl where every morning she doesn't remember who he is, he's forced to be the most committed you can possibly be in a romantic relationship as the story teaches the good message that love doesn't tarnish or grow complacent.
The amazing story is absolutely beautiful and the cast is stacked through the roof with awesome actors as well. Drew Barrymore and Adam Sandler continue to have some of the best on-screen chemistry in rom-com history, Sean Astin was absolutely hilarious, Dan Akroyd was as awesome as ever and c'mon, who doesn't love Rob Schneider? 50 First Dates is easily one of Adam Sandler's best movies and I'm a huge fan of it, so if you haven't seen it I couldn't recommend it more.
4 - The Waterboy (1998)
My brother's guitar teacher once said that if Happy Gilmore and Billy Madison were Adam Sandler putting everything in place to make the perfect movie, then The Waterboy would be that perfect movie. It's an excellent mother-and-son bonding story with an awesome performance from Henry "The Fonz" Winkler along with a hilarious spin of Adam Sandler tackling people conveying the positive message that anyone can be a hero.
Countless scenes out of here are utterly hilarious. The noises Sandler makes whenever he tackles people crack me up, the whole "Mamma says" scene is amazing and all the baiu jokes just make the movie even better. This movie also introduced Rob Schneider's character Towney to the Sandlerverse, and thank goodness for that because from now on whenever a friend of mine is having self-esteem issues or just needs a little encouragement, I can't help but exclaim to them four powerful words of wisdom: "YOU CAN DO EET!"
3 - Click (2006)
I put on Click expecting a simple, funny Adam Sandler movie that would be enjoyably hilarious and passed the time, but when I took it out of the DVD player I had finished watching a tragic but beautiful masterpiece that remains extremely underappreciated by the morons who work for Rotten Tomatoes. Overall, this film is a well put together, gradually intensifying masterpiece that brought a good new approach to Adam Sandler movies and helped me rethink my view on life.
I don't really want to give this movie away because I want people to watch it, but in general Click is an excellent movie that goes to all time devastating lows before teaching the audience positive messages about putting family first, enjoying every second of life and the universe being whatever you make of it. Christopher Walken, Sean Astin, David Hasslehoff and Henry Winkler were all very good in this movie and I was all around on the edge of my seat for the vast majority. The film really reminded me that Frack Coraci really was my favorite Happy Madison director and I honestly couldn't recommend this movie enough. It's fantastic.
2 - The Wedding Singer (1998)
I can assure you that you'll have a hard time trying to find a "best Adam Sandler movies" list without at least putting this in the top 20. Go ahead, try. That's simply how good The Wedding Singer is. The movie is perfect on absolutely every level possible. I probably relate to Robby Hart's personality more than I relate to any other Adam Sandler character, and his arc is really good as this movie deals with the importance of having one person you can spend the rest of your life with. I mean, c'mon, who doesn't choke up at one point or another during Grow Old With You?
Adam Sandler and Drew Barrymore's chemistry continues to be awesome in this film, probably even surpassing 50 First Dates, and there are all kinds of awesome moments through the whole movie that make me die laughing. The entirety of Somebody Kill Me, the killer line about getting out of the "Van Halen t-shirt before you jinx the band and they break up", John Lovitz's hilarious performance of Ladies Night, Steve Buscemi's best man speach, the entire George character and more all make this movie totally hilarious and on both the fronts of humor and heart, The Wedding Singer delivers a strong entertaining classic.
1 - Pixels (2015)
I get that it isn't the most popular choice for the best Adam Sandler movie, but Pixels is and will always be my all time favorite Happy Madison movie and I hold it very close to my heart. Every character in this movie is fantastic and had very good arcs. Sam Brennor learned about putting his talents to a good use, President "Chewie" Cooper showed growth towards gaining confidence and being a better leader, Ludlow Lamonsoft proved himself more than just a basement nerd as he scored on the fictional girl of his dreams while Violet Van Patten revolutionized the trope of VV initialized Sandler love interests as more than just a generic crush but an actual multi-dimensional character and Eddie "Fireblaster" Plant, the awesome Peter Dinklage character, has all the best lines and a good arc about proving to yourself you're not a cheater.
This movie's story was great and it really inspired me. All my life I've never been the strongest, fastest or smartest kid at school, I've just filled my brain with overwhelming amounts of useful information about fictional universes that I spend more time in than the real world. Pixels however gave me hope that maybe someday I can use my endless pop culture knowledge to accomplish something great, and I remember that every time I'm insulted for being too big of a nerd or whatever.
I'm a huge retro video game nerd and I love Chris Columbus as a director for his work on films like Goonies and Gremlins, so this was always bound to be my favorite Adam Sandler movie. I must've seen this movie a million times, it's at the point where I know every line, and I relate to every main character to some extent, especially Josh Gad as Ludlow. This movie never gets old, Rotten Tomatoes can eat dirt for what they said about it and in general, Pixels is one of my favorite movies ever made so it easily makes the top of the list.
In conclusion, those are my ten favorite Adam Sandler films. I love Adam Sandler as an actor and I always can find some spark of joy from watching a movie of his (yes, even Jack and Jill and The Ridiculous 6) so I'm very excited to see his upcoming more serious movie, Hustle, based on a true story about basketball coming this June. Thanks for reading, everyone!
Stay geeky,
-Jack Higgins