Adam Sandler: His best films and movies ranked – Happy Gilmore to Uncut Gems

From outrageous comedies to gritty thrillers, we rank Adam Sandler’s best ever film roles, including The Wedding Singer, Hustle, Big Daddy, Uncut Gems and more.

By Alex Fletcher Published: 8 March 2023 - 1.54pm
Warner Bros Drew Barrymore and Adam Sandler in The Wedding Singer

From blockbuster comedies of the ‘90s to critically acclaimed award-winners on Netflix, Adam Sandler has a surprisingly diverse back catalogue of movies.

Slated by critics but adored by the masses, Adam Sandler might divide opinion, but his films continue to put bums on seats.

The New York comedian, who first found fame on Saturday Night Live, returns to Netflix in 2023 with Murder Mystery 2. The crime caper, co-starring Jennifer Aniston, is the classic Sandler cocktail of outrageous behaviour and snigger-filled humour. The original remains one of Netflix’s most-watched films of all time and the sequel looks likely to follow suit.

Ahead of the movie’s release on 31 March, we’ve ranked our 10 favourite Adam Sandler films. Did your favourite make the top 10?

The 10 best Adam Sandler films - ranked

10. The Week-Of (2018)

Adam Sandler’s fourth Netflix movie found the comic actor co-starring with his fellow Saturday Night Live alumni Chris Rock.

Sandler and Rock star as two fathers whose children are marrying each other. Sandler’s construction worker Kenny refuses to accept any money from wealthy doctor Kirby (Rock) for the wedding and his efforts on a limited budget are the source of spiralling chaos.

Watch The Week-Of now on Netflix.

9. Billy Madison (1995)

Adam Sandler’s first lead role on the big screen was as Billy Madison, the child-like 27-year-old sent back to complete his school education by his wealthy father.

The movie set a trend all Sandler films would follow in the ‘90s, getting mauled by the critics and adored by fans.

Co-starring Norm Macdonald, Bridgette Wilson and Bradley Whitford, Billy Madison is childish but great fun and has built up a cult status.

8. Murder Mystery (2019)

Jennifer Aniston and Adam Sandler in Murder Mystery Netflix

Before Knives Out revived Hollywood’s interest in whodunnits, Murder Mystery was a surprisingly fun spoof of the classic crime caper format.

Sandler and Jennifer Aniston reunited for the first time since 2011’s Just Go With It and it feels like the duo are having a great time together. Aniston in particular showcases her underrated comic chops, playing it straight while everyone else is in goofball overload.

Watch Murder Mystery now on Netflix.

7. Happy Gilmore (1996)

If you were a teenager in the ‘90s, it’s highly likely you watched this movie on repeat and can quote endless lines of Sandler’s screaming dialogue.

Sandler stars as short-tempered ice hockey player Happy Gilmore, who discovers his slapshot technique could provide him with a way of paying off his grandmother’s tax-bill. The only problem is that his whacking skills require he switches from hockey to the more dignified and snooty world of golf.

Christopher McDonald stars as Gilmore’s arrogant opponent and Julie Bowen (Modern Family) is Sandler’s love interest Virginia Venit.

6. The Meyerowitz Stories (2017)

Ben Stiller and Adam Sandler in The Meyerowitz Stories Netflix

Since becoming a regular collaborator with Netflix, Sandler’s work has become incredibly diverse. One moment he’s releasing broad comedy like Murder Mystery or Hubie Halloween, and then the next he’s teaming up with Noah Baumbach (Marriage Story, The Squid and the Whale) for Palme d’Or and Cannes Film Festival winner The Meyerowitz Stories.

An emotional comedy about three siblings (Sandler, Ben Stiller and Elizabeth Marvel) living under the shadow of their domineering father (Dustin Hoffman), Sandler gives one of his greatest performances and is the standout actor in a movie, which also stars Emma Thompson, Grace Van Patten and Adam Driver.

Watch The Meyerowitz Stories now on Netflix.

5. Punch-Drunk-Love

Director Paul Anderson (Magnolia, There Will Be Blood, Licorice Pizza) spotted something in Sandler many hadn’t seen before. This serious and surreal romantic-comedy shifted him outside his normal goofy humour for his performance as bachelor Barry Egan.

Co-starring Emily Watson and Philip Seymour Hoffman, the film was ironically a rare box office bomb for Sandler, despite the fact it earned him some rare praise from the critics.

4. Big Daddy (1999)

Yes, it’s crude. Yes, it’s predictable. No, it’s not clever. Yes, it won Razzies. But darn it, Big Daddy is just funny.

Sandler and Happy Gilmore director Dennis Dugan reunite to tell the story of Sonny Koufax, a 32-year-old man gets dumped by his dream girl for not growing up. How does he respond? By adopting a five-year-old boy, of course.

As long as you don’t go in expecting anything remotely sophisticated, you’ll have a great time watching Big Daddy.

Watch Big Daddy now on Netflix.

3. The Wedding Singer (1998)

An Adam Sandler comedy film that even people who don’t like Adam Sandler films enjoy. Sandler and Drew Barrymore are beguiling and utterly believable as the leads in this sunny and playful 80s-set rom-com.

Sandler plays Robbie Hart, a wedding singer, opposite Barrymore as waitress Julia. The duo bring out the best in each other as the feel-good love story unfolds.

If you want an Adam Sandler comedy, this should be first on your list.

2. Hustle (2022)

Adam Sandler in Hustler Netflix

One of the most remarkable parts of Adam Sandler’s basketball movie Hustle is that it isn’t based on a true story.

The heartwarming and inspiring story of a down-on-his-luck NBA scout Stanley Sugerman (Sandler) and Spanish basketball player Bo Cruz (Juancho Hernangómez) feels so natural and authentic, you’re left presuming that this must be based on a real rags-to-riches story.

Sandler is at his relaxed best and most appealing as Sugerman, ably supported by Queen Latifah as his wife Teresa.

Watch Hustle now on Netflix.

1.  Uncut Gems (2019)

Adam Sandler in Uncut Gems Netflix

For anyone who only knew Adam Sandler through his box office comedy hits of the ‘90s, Uncut Gems came out of nowhere. It’s a truly formidable performance from Sandler, which shocked and stunned many and in hindsight deserved more major awards recognition than it received.

Sandler stars as jeweller and gambling addict Howard Ratner, who needs to get his hands on a gem to pay off his debts.

It’s 2 hours 15 minutes of stomach-churning anxiety which is unquestionably Sandler’s finest movie to date.

Watch Uncut Gems now on Netflix.