Adam Sandler is one of Hollywood’s most loved actors, but his movies haven’t always been considered the best. Critics may savage his movies, but Sandler has a large fanbase of devoted followers who thoroughly enjoy his films. Unlike critics who despise films like You Don’t Mess With the Zohan and Mr Deeds, general film viewers adore them. Sandler’s films offer an easy escape and a chance to laugh at Sandler’s bumbling characters, who are always caught up in fun and exciting scenarios that tickle the funny bone.
Sandler has proven he is not just a comedic actor but has branched into dramatic roles such as Punch-Drunk Love, Uncut Gems and Spaceman, proving he is not a one-trick pony, but a celebrated actor with range, who can turn in a funny and serious performance.
Sandler’s broad appeal is due to his vulnerability and his characters’ unassuming persona. Everyone roots for the Waterboy or Happy Gilmore, and this ability to connect with audiences made Sandler famous. In honour of his work, let’s look at some of Sandler’s most popular and best-loved films.
10. Mr Deeds (2002)
Winona Ryder stars as Babe Bennet, a tabloid reporter who disguises herself as Pam Dawson, a school nurse, to get close to and gather information on Deeds, played by Adam Sandler. Deeds is heir to a sizeable fortune from a billionaire uncle he never knew he had. After his uncle passes away during an unfortunate mountain expedition, Deeds inherits his fortune. Still, it comes with a few hiccups and a plan hatched by schemers to rob Deeds of his money.
The plot is predictable, but the film is nonetheless a joy to watch. Sandler and Ryder are great together, especially Ryder, who excels in this comedic role, playing her character with callousness and sweetness. Deeds is a funny and captivating rags-to-riches story loaded with rewatchable qualities for its heart, humour and fun. Although it’s technically at the bottom of the list, Mr Deeds is still one of the best Adam Sandler movies of all time.
9. 50 First Dates (2004)
Sandler plays Henry Roth, a womanizing marine veterinarian who falls for an art teacher named Lucy (Drew Barrymore). When he discovers she has amnesia and forgets him when she falls asleep, he resolves to win her over again each new day.
Sandler and Barrymore reunite in a romantic comedy for the second time after The Wedding Singer, and later, they would once again star in Blended, completing a trilogy of rom-coms for the duo. 50 First Dates has lots of crude humour, but its story is sweet and uplifting enough to compensate for the low-brow humour. Sandler and Barrymore are great together, and Sandler drops the anger schtick of previous movies to reveal his gentler side.
8. Happy Gilmore (1996)
Happy Gilmore is a sports comedy film directed by Dennis Dugan, starring Adam Sandler as Happy, Christopher McDonald as the main antagonist, Shooter McGavin, Julie Bowen as Virginia, Happy’s love interest, and Carl Weathers as Derick “Chubbs” Peterson. It tells the story of an unsuccessful ice hockey player (Gilmore) who discovers a newfound talent for golf and competes in a golfing tournament to save his grandmother’s home from foreclosure.
Shooter despises Happy, hating his lack of golfing etiquette and tries his best to stop Happy from winning a gold tournament. Happy’s lack of refinement and anger-fueled outbursts on the golfing course make this Sandler movie so funny. Carl Weathers, as Chubbs, Happy’s coach, also gives an excellent performance. His fake hand being eaten by an alligator is a hilarious running joke throughout the movie.
7. Anger Management (2003)
Another classic screwball comedy in which Sandler (Dave Buznik) stars alongside Jack Nicholson, who plays an unorthodox therapist, Dr Buddy Rydell. Dave suffers from repressed rage due to being humiliated as a kid. After an incident on an aeroplane, Buznik is sentenced to anger management classes with Dr Rydell, whose unusual methods drive Dave crazy.
The interplay between Nicholson and Sandler is comedy gold and will leave you in stitches. Watching Rydell antagonize Dave by using passive-aggressive behaviour to help Dave manage his unchecked anger and rage causes plenty of great on-screen tension and chemistry between them. Nicholson is brilliant, as his comedic timing and delivery are superb. Sandler sheds the childish image, and the plays are slightly more complex characters than what viewers are used to. Still, Sandler gives a hilarious portrayal of Dave.
6. Billy Madison (1995)
Sandler is the king of acting like a petulant man-child. Billy Madison plays into Sandler’s penchant for this form of humour. The actor stars as Billy, a spoilt, dimwitted heir to the Madison Hotels chain. Before claiming his inheritance, Billy has to prove to his wealthy father he can run the family business. In a bizarre but funny proposal, Billy promises to redo all 12 school grades, which he blunders through in a few months.
Billy Madison is Adam Sandler at his comedic best. Billy is an oddball, loser character who wins in the end. It doesn’t matter how unconventional you are; if you’re true to yourself, you can overcome the difficulties in your life. The movie is true to these concepts and is part of Sandler’s widespread appeal, portraying characters like Billy, unconventional losers but likeable and sincere at heart.
The other reason the film is so loved is that it’s over-the-top funny. Yes, Sandler is irreverent, and the film is loaded with puerile jokes, but if you’re not too uptight, then Sandler’s humour can put a smile on your face and force a laugh out of you. This hilarious nugget of Adam Sandler history is, without a doubt, one of his best movies.
5. Big Daddy (1999)
Big Daddy is one of Sandler’s best films as far as its use of adult and juvenile humour. Sandler plays Sonny Koufax, a man-child who refuses to grow up and become a responsible adult. His girlfriend dumps him because he refuses to move to the next phase of their relationship. After a five-year-old kid is left at his front door, Sonny decides to take care of the kid to prove to everyone, especially Vanessa, his ex-girlfriend, that he is a responsible adult.
Sandler can convey a sense of naivete and innocence that imbues many of his characters, and Sonny is one of these. The crude jokes and cliche plot points are offset by genuinely funny moments and a warm sentimentality that appeals to moviegoers looking to laugh and enjoy a heartwarming story.
4. Uncut Gems (2019)
In this Safdie brothers crime thriller, Sandler plays jeweller and gambling addict Howard Ratner. The actor gives his most un-Sandler-like portrayal as Ratner, and the film marks the definitive example of Sandler being a legitimate actor who has moved beyond making silly comedies. While he will always be known for outrageous comedic roles, films like Uncut Gems show how talented the actor truly is and put to bed accusations that Sandler cannot carry a movie in a dramatic role.
3. Spanglish (2004)
Spanglish is not well known by most Sandler fans. The sweet family comedy wasn’t typical Sandler fare, which alienated average filmgoers looking for a typical blue-collar comedy; neither was it avant-garde like Punch-Drunk Love, a movie beloved by critics. Thus, Spanglish fell between the cracks, not appealing to generic Sandler fans or critics.
Sandler portrays John Clasky, a mild and meek chef, in the throes of marital problems with his wife, Deborah (Tea Leoni). Flor, the Clasky family’s new maid and her daughter Cristina help the Claskys figure out their problems and become a loving, close-knit family once more.
Spanglish is charming and a great mix of comedy and drama. Sandler is great at burrowing into your heartstrings and making viewers root for him because he is so good at being vulnerable. John is a vulnerable character who wears his heart on his sleeve, and Sandler moves effortlessly between being dramatic and funny.
2. Punch-Drunk Love (2002)
Punch-Drunk Love was a marked departure from Sandler’s typical comedic roles. The actor shocked everyone when he starred as the introverted businessman Barry Egan. The character’s frayed psychology, tainted with anger, anxiety and loneliness, was consummately portrayed by Sandler, who received wide acclaim for his role.
Although the film failed to connect with audiences, it became a cult classic. It was the launchpad for Sandler to appear in other dramatic roles. Director Paul Thomas Anderson wrote the part with Sandler in mind after being impressed with Sandler’s surprisingly broad acting range. He noted how Sandler could go from mild and introverted to exploding rage at the drop of a dime and created Barry as a vehicle for Sandler to explore.
Punch-Drunk Love is an unconventional romantic comedy that takes all of Sandler’s quirks and reconstitutes them into an arthouse film. The film subverts the rom-com genre and tries to dig a little deeper by using damaged and unconventional characters to show how love can be found in the most unlikely places, even for those unlucky and unable to find someone who understands them.
1. The Wedding Singer (1998)
The late 90s and early 2000s were a hotbed of funny, irreverent comedies. Adam Sandler was one of comedy’s pioneers during this golden age. The Wedding Singer is a perfect blend of Sandler’s charm and humour but without the gross-out excesses and childish behaviour of many of Sandler’s other characters.
Yes, all these elements critics hate are present. Still, they’re toned down and constrained by a sweet storyline about Robbie (Adam Sandler), a wedding singer whose fiance dumps him. He falls in love with Julia, a waitress played by Drew Barrymore. Sandler doesn’t just portray a goofy, one-dimensional character like he did in previous films.
Robbie is more rounded and nuanced but also incredibly likeable and funny. Sandler also nails the wedding singer persona. The film’s enduring appeal also stems from its ’80s setting, which adds a sense of nostalgia and whimsical idealism running in the film’s background. This early classic is easily one of the best Adam Sandler movies out there.
Which Adam Sandler films would you have included in this list of the best movies he has ever made?
