in chronological order
Adam Sandler has had an expansive career in Hollywood films for the past few decades. While he is especially known for comedies, some of his best work is in his more serious roles. My ranking will only include movies that I have seen, as well as movies where he isn’t a starring role.
1. Happy Gilmore (1996)
Happy Gilmore (Adam Sandler) dreams of being a professional hockey player, but to his dismay, no one will take him seriously. He discovers that he is capable of swinging incredibly long distances for golf, which is not a talent he wished for. When his grandmother’s home is at stake, Happy enters a golf tournament in hopes of winning the grand prize so he can save the beloved house. This is one of Adam Sandler’s most iconic movies, and for good reason. Between Happy Gilmore’s comedic and untamed anger issues, coupled with big star cameos, this movie is a perfect watch for stress relief at the end of a long week. What makes this movie truly special is that you don’t even have to like sports to enjoy it!
2. Big Daddy (1999)
Sonny (Adam Sandler) is a very childish man in his thirties who was recently dumped by his girlfriend for a much older and more mature man. Sonny, in an attempt to win her back by displaying his maturity, decides to adopt the 5-year-old child who was mistakenly dropped off at his door. This movie is hilarious, heartwarming, and surprisingly emotional. Adam Sandler’s character is an astoundingly irresponsible parent throughout most of the film, yet I found myself rooting for him as his relationship with his adopted son grew. Their deep bond is undeniable and emphasizes the “found family” theme in this movie. Overall, this movie has a refreshing take on adulthood: it is perfectly okay to hold on to one’s childish side, just as long as bills still get paid!
3. Mr. deeds (2002)
Longfellow Deeds (Adam Sandler) lives in a small town and lives a simple life. He works at a pizza restaurant and writes cards which he hopes Hallmark will buy from him. That is, until one day he finds out he is the sole inheritor of a long-lost relative’s multi-billion fortune and media company. Adam Sandler’s character is endearingly naïve when it comes to the press, and human nature in general. This comedy is filled with unexpected plot twists, romance, and so much more. It is definitely worth watching!
4. Anger Management (2003)
Dave Buznik (Adam Sandler) is a normal man, living a mundane life with his girlfriend. One day, an incident on a plane forces him to attend anger management classes or be sent to jail. Dave is shocked and confused by this, he believes he did nothing wrong but agrees to attend the classes to avoid jail time. His teacher’s (Jack Nicholson) lessons are unconventional, to say the least. This movie will take the viewer on all kinds of outlandish adventures and leave them thinking, “What did I just watch?” in the best way possible. This cast could not be any better and makes the movie all the more enjoyable to watch.
5. 5o first dates (2004)
This movie follows Henry (Adam Sandler), a man who lives in Hawaii and relies on the steady flow of tourists for no-strings-attached dates he will never see again in his reluctance to settle down. That is until he meets Lucy (Drew Barrymore), a kind and beautiful local. They hit it off, and he finds himself wanting to start a serious relationship with her, only to find out that she has short-term memory loss after an accident and forgets the previous day. Henry refuses to give up on her and sets himself on a mission to make her fall for him again every day. This is the ultimate comfort movie for me, it makes me laugh and cry, and I find myself falling in love with it after each watch, even though I’ve seen it about 50 times! It is deeply emotional but has plenty of comic relief, plus one of the supporting roles is a penguin!
6. Spanglish (2004)
A Mexican immigrant single mother Flor (Paz Vega) takes a job as a housekeeper for Deborah (Téa Leoni) and John (Adam Sandler). She moves into their house with her daughter. The two families find more complications than they expected, between their different cultures and different parenting styles. This movie is emotional and touching seeing how Flor navigates the world as a single mother and an immigrant, in comparison to Deborah who seems to have an effortless life that she barely had to work for. It is fascinating to see how Deborah’s carefully constructed life is much more fragile than the viewer initially believes it to be. As for Adam Sandler’s character, no spoilers, but this is a much different role for him than his usual raunchy and comedic parts.
7. Click (2006)
Michael (Adam Sandler) gets a universal remote for his TV, only to discover that it controls time. He is thrilled by this discovery and uses the remote liberally to skip parts of his day that he finds “boring”. The remote begins to learn his behaviors and begins to skip certain tasks without Michael pressing a button. This movie is layered with comedy, emotion, regret, and lessons. It left me far more impacted than some of Sandler’s typical comedic movies by having me value, and even look forward to, some of the tasks that I had previously thought of as “boring”.
8. I now pronounce you chuck and larry (2007)
Chuck (Adam Sandler) and Larry (Kevin James) are firefighters and best friends. In an effort to help Larry add his children as beneficiaries to his life insurance, Chuck agrees to become Larry’s legal domestic partner. Although Chuck and Larry are both straight men, the struggles they face are very reminiscent of the time. This movie is both incredibly funny, as well as enlightening to LGBTQ+ rights in a time when gay marriage wasn’t legal in the United States yet. Adam Sandler and Kevin James are an iconic duo you didn’t know you needed until you see them together. It is really enheartening to watch a movie where cisgender straight men advocate for LGBTQ+ rights.
9. grown ups (2010)
After reuniting during the funeral services of a beloved Little Leagues basketball coach, five childhood friends (Adam Sandler, Kevin James, Chris Rock, Rob Schneider, David Spade) and their families share a summer house together. This hilarious group bonds and comes together to face old rivals. Adam Sandler and his castmates have incredible chemistry, as they are friends off camera, making this movie all the more enjoyable. This is a great movie to watch in the summer, or when you’re especially missing the summer. It is filled with laugh-out-loud moments targeted for all age groups as well!
10. Just Go with it (2011)
Once again Adam Sandler plays a character, Danny, who is reluctant to settle down. He uses a wedding ring and a made-up sob story to make women pity him enough for a no-strings-attached evening because, after a real heartbreak, he doesn’t want to go through the pain again. This all changes when he meets a gorgeous and much younger woman with whom he actually has a connection and convinces his assistant Katherine (Jennifer Aniston) and her kids to pretend to be his soon-to-be ex-wife and children. This Rom-Com is a must-watch and seems to get funnier every time I see it. The whole cast has great chemistry making even the most ridiculous points of this movie believable.