The best Adam Sandler movies

Chris Tilly
Adam Sandler in Uncut Gems.

From dumb comedies and animated flicks to sports films and serious dramas, these are the best Adam Sandler movies.

Adam Sandler is one of the most successful actors in the world. Over a career that has lasted more than 30 years, he’s starred in hit movies on an annual basis, some of them cult hits, others bona fide blockbusters.

And while he initially focussed on low-brow comedies like Billy Madison and Little Nicky, Sandler has recently combined laugh-fests with more serious fare that has won him both acclaim and awards.

Adam Sandler has therefore crafted one of the most interesting careers in Hollywood, and these are the best of his films.

The Best Adam Sandler movies

The following are the 11 best Adam Sandler movies, listed from worst to best.

The only criteria is that we’ve focussed on movies where he plays one of the leads, rather than those where he cameos or is just a supporting player.

11. The Waterboy

Synopsis: Just an oddball mama’s boy from the back bayous of Louisiana, Bobby Boucher never wanted anything more than to quench the thirst of the dehydrated athletes who treat him like dirt. But when Coach Klein makes the call that allows Bobby to finally stand up for himself, it unleashes a torrent of bottled-up frustration… and exposes a talent for tackling that transforms him from a meek “water distribution engineer” to the hardest hitter ever to roam the gridiron!

The movies where Adam Sandler does that voice aren’t for everyone. But Waterboy works, as both dumb comedy, and inspiring sports movie. Though it’s Kathy Bates who steals the movie as Bobby’s eccentric mama, Mama.

10. Murder Mystery (2019)

Synopsis: When an NYC cop finally takes his wife on a long promised European trip, a chance meeting on the flight gets them invited to an intimate family gathering on the Super Yacht of elderly billionaire Malcolm Quince. When Quince is murdered, they become the prime suspects in a modern day whodunit.

Murder Mystery is a blast, teaming two comedy heavyweights in the shape of Sandler and Jennifer Aniston, and dropping them into the middle of a thrilling murder mystery. They make a winning couple, the whodunit at the heart of the story is filled with twists and turns, and the movie was such a success that Netflix quickly green-lit a sequel which released earlier this year.

9. 50 First Dates (2004)

Synopsis: Henry Roth is a man afraid of commitment up until he meets the beautiful Lucy. They hit it off and Henry think he’s finally found the girl of his dreams, until he discovers she has short-term memory loss and forgets him the next day.

50 First Dates is a high-concept flick that asks “What if Memento were a romantic comedy?” Sandler had already established great chemistry with Drew Barrymore in The Wedding Singer (further down this list) and here they again light up the screen as a couple whose new relationship is scuppered at every turn by her daily memory loss.

8. Anger Management (2003)

Synopsis: After a small misunderstanding aboard an airplane escalates out of control, timid businessman Dave Buznik is ordered by the court to undergo anger management therapy at the hands of specialist Dr. Buddy Rydell. But when Buddy steps up his aggressive treatment by moving in, Dave goes from mild to wild as the unorthodox treatment wreaks havoc with his life.

Jack Nicholson is the doctor and Adam Sandler is the patient. But Sandler should be the doctor and Nicholson the patient in this lewd, crude, rude, and very funny film about dealing with anger issues. The supporting cast also elevates the material, with the likes of John Turturro, John C. Reilly, Woody Harrelson, Luis Guzman, and Marisa Tomei delivering hilarious cameos.

7. Hotel Transylvania

Synopsis: Welcome to Hotel Transylvania, Dracula’s lavish five-stake resort, where monsters and their families can live it up and no humans are allowed. One special weekend, Dracula has invited all his best friends – Frankenstein and his wife, the Mummy, the Invisible Man, the Werewolf family, and more – to celebrate his beloved daughter Mavis’s 118th birthday. For Dracula catering to all of these legendary monsters is no problem but the party really starts when one ordinary guy stumbles into the hotel and changes everything.

Adam Sandler joints sometimes look less like movies, and more like glorified vacations for him and his actor buddies. Particularly the Grown-Ups films. Hotel Transylvania takes that same ensemble – David Spade, Kevin James, Steve Buscemi and the like – and gives them actual funny stuff to do, in an animated caper that pokes fun at classic monster movies.

6. Airheads (1994)

Synopsis: The Lone Rangers – a desperate and struggling Los Angeles rock n roll band – inadvertantly take a radio station hostage when they try to get their demo played.

Bill and Ted and Wayne and Garth were the most famous dumb rockers of the early 1990s. But The Lone Rangers of Airheads were just as dopey, and just as funny. Brendan Fraser, Steve Buscemi and Sandler play the misguided musicians in question, while Chris Farley is on scene-stealing form as an equally dopey cop.

5. Funny People (2009)

Synopsis: When famous comedian George Simmons is given a second chance at a new beginning, he and his assistant, struggling comedian Ira, return to the places and people that matter most, including the stand-up spots that gave him his start, and the girl that got away.

The first of our serious Sandler movies finds him playing a comedian, but one for whom a health crisis inspires an existential crisis. Seth Rogen is the aspiring stand-up who lands a job as his assistant, and their complicated relationship sparks both laughter and tears via Judd Apatow’s sharp scrip.

4. Happy Gilmore (1996)

Synopsis: Failed hockey player-turned-golf whiz Happy Gilmore is determined to win a PGA tournament so he can save his granny’s house with the prize money. Meanwhile, a tour publicist tries to soften Happy’s image.

The funniest film on this list features a solid Sandler performance as the titular golfer with an unorthodox swing, and Happy Gilmore successfully skewers the sport. But Christopher McDonald’s ‘Shooter McGavin’ is the film’s MVP, closely followed by Ben Stiller hilariously evil nurse.

3. Punch-Drunk Love (2002)

Synopsis: Although susceptible to violent outbursts, bathroom supply business owner Barry Egan is a timid and shy man by disposition, leading a lonely, uneventful life – partly due to the constant berating he suffers from his seven sisters. However, several events transpire that shake up Egan’s mundane existence, one of which is falling in love with one sister’s co-worker, Lena Leonard. But the romance is threatened when Egan falls victim to an extortionist.

Another angry Adam Sandler performance, but this one comes courtesy of acclaimed writer-director Paul Thomas Anderson. And Punch-Drunk Love is a good deal more serious than what’s gone before, with Sandler going toe-to-toe with acting heavyweights like Emily Watson and Philip Seymour Hoffman, and more than holding his own.

2. The Wedding Singer (1998)

Synopsis: Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other.

Adam Sandler comedies are frequently cruel and mean. The Wedding Singer is the opposite, being both sweet and warm-hearted. In their first onscreen coupling, Sandler and Drew Barrymore are adorable. While Tim Herlihy’s script smartly satirises weddings, as well as the sounds and fashions of the 1980s. Plus, who can forget that rapping Granny?

1. Uncut Gems (2019)

Synopsis: With his debts rising, and angry collectors closing in, a fast-talking New York City jeweller risks everything in hopes of staying afloat and alive.

Uncut Gems is less a movie and more a sustained assault on the senses, inducing insane amounts of anxiety as the protagonist’s problems mount, and his situation becomes ever-more dire. In a performance entirely devoid of vanity, Sandler guy plays the jeweler in question like a man possessed, while writer-directors the Safdie brothers give him some of the best dialogue of his career. And while it’s a sometimes painful watch, Uncut Gems is also Adam Sandler’s best movie.

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