The best Adam Sandler movies of all time

You may think a list of the best Adam Sandler movies would only include comedy movies from the late '90s and early 2000s, but you'd be wrong

Best Adam Sandler movies

What are the best Adam Sandler movies? Through the late ’90s and early 2000s, there were few big-screen stars who could go toe-to-toe with comedy movie legend Adam Sandler and his incredible box-office power.

Jim Carrey (who some unfairly pitted against Sandler), Will Smith, and Tom Cruise were perhaps the only actors who were above him, meaning he still enjoyed enormous success. In the years between 1998 and 2014, he had 18 films gross well over $100 million worldwide, and many of those earned just as much in the US alone – no easy feat.

While the quality of those films is open for debate (Editor: You are not wrong), there’s no doubting the comedian’s popularity, and even though he ended up making his most recent work with streaming service Netflix, Sandler is as popular as he has ever been. As such, we decided to have a decent stab at compiling a list of the best Adam Sandler movies from across his extensive career.

What are the best Adam Sandler movies?

  • Reign Over Me
  • Happy Gilmore
  • The Meyerowitz Stories
  • The Wedding Singer
  • Funny People
  • Uncut Gems
  • Punch Drunk Love

Best Adam Sandler movies: Don Cheadle and Adam Sandler in Reign Over Me

Reign Over Me (2007)

Suppose you liked seeing Sandler do something a little different with Uncut Gems. In that case, you should seek out Reign Over Me, arguably the most underrated and underseen film in the comedian’s vast catalogue of performances.

A much more dramatic turn than perhaps all of his steps towards more serious roles, here he is the complete opposite of his outlandish, goofy, loud ‘man-child’ persona.

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Sombre, quiet, and broken, Sandler stars as Charlie Fineman in this drama movie, a New York doctor of some note who is still reeling from the tragic loss of his wife and daughters who died in the 2001 terrorist attacks on the Twin Towers.

He slowly starts to address his repressed anger and heartbreak thanks to his old college roommate (Don Cheadle), who re-enters his life and seeks to bring Charlie back from the brink.

Best Adam Sandler movies: Carl Weathers and Adam Sandler in Happy Gilmore

Happy Gilmore (1996)

After breaking through on Saturday Night Live in the early ’90s, Sandler was seen as one of the show’s big stars (alongside Mike Myers, for example) during some rocky years before the emergence of Will Ferrell, Kristen Wiig, Tina Fey, and more.

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Taking small steps into films with Mixed Nuts, Coneheads, and Airheads, he started to emerge as a star in the middle of the decade, and Happy Gilmore marked his big breakout.

Combining his crude, vulgar sensibilities with the modest, quiet game of golf was electric, and punctured with some hilarious moments as well as some touching ones. It has become something of a cult classic in the years since, celebrating its 25th-anniversary last year.

Best Adam Sandler movies: Ben Stiller and Adam Sandler in Meyrowitz Stories

The Meyerowitz Stories (2017)

This one may well have flown under your radar since its release. The Meyerowitz Stories was one of the first high-profile ‘awards season’ Netflix originals to be released. With Sandler under contract with the streamer, it was a no-brainer to snap up the film after its four-minute standing ovation at Cannes in 2017.

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Allowing Sandler to flex his more mature muscles while still allowing his normal persona to peek out (in fact, it’s something of an older version of it), Noah Baumbach’s sharp, beautiful tale of family dysfunction in the Big Apple saw Sandler at odds with his half-brother Matt (Ben Stiller), father (Dustin Hoffman), and daughter Eliza (Grace van Patten).

Best Adam Sandler movies: Adam Sandler as Robbie Hart in The Wedding Singer

The Wedding Singer (1998)

Fuelled by one of ’90’s best opening credits – a wedding in full swing as Sandler serenades those dancing with his rendition of Dead or Alive’s ‘You Spin Me Round’ – The Wedding Singer was one of the big surprises of 1998 both at the box-office and in its critical acclaim.

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Sandler’s roster of films before this one – Happy Gilmore and Billy Madison, amongst others – was aimed at a younger audience but, paired with Drew Barrymore (who he would team with again twice more in the years since), the film skewed slightly older with its romantic elements and became a sensation. Grossing over $100 million on its minute $18 million budget, it spawned a Broadway musical and is considered one of the ’90’s best rom-coms.

Best Adam Sandler movies: Adam Sandler and Seth Rogen in Funny People

Funny People (2009)

Here’s a fun nugget of info for you. When he was in college, Sandler was roommates with writer/director Judd Apatow (and good friends with Ben Stiller). For many years through their careers, it was assumed that the trio would work together at some point but seemingly, they didn’t want to just make a ‘comedy’, as many would-be anticipating.

Apatow had been toying with telling a story of a stand-up comedian (where he and Sandler had started out) becoming a mentor for a young comedian (played by Seth Rogen), and he thought of Sandler to play the lead of George Simmonds, a character who leaned heavily into his real career.

As with other more dramatic-leaning roles, Funny People marked another win for Sandler despite the film not performing quite how many had predicted (people were anticipating a more mainstream comedy film from the duo), but his delicate, nuanced performance is one of his very best and most underseen.

Best Adam Sandler movies: Adam Sandler as Howard Ratner in Uncut Gems

Uncut Gems (2019)

Sorry, we meant ‘Unka Jahms’, of course. It seems like a decade ago that the Safdie Brothers’s scorching hit was released due to the pandemic and everything else going on in the world, but it was under three years ago.

A sensation when it was unleashed on the world, both on the back of Safdies’s previous film Good Time and the lure of Sandler ‘stepping out’ of his usual schtick, no one was quite prepared for what Uncut Gems was.

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Described as “anxiety-inducing cinema” and “cinema of pure energy and grungy voltage” by critics, the film garnered international praise, as did Sandler, who went on to win many awards, including the Best Actor gong at the Independent Spirit Awards. If you have never seen his acceptance speech, Google it immediately.

Best Adam Sandler movies: Adam Sandler as Barry Egan in Punch Drunk Love

Punch Drunk Love (2002)

Reading through this list, it will undoubtedly surprise many that most of those on the list of Sandler’s best performances aren’t the out-and-out comedies that helped make his name.

We can’t help it: when he goes serious/half-serious, he delivers and out in front as his best and most unexpected turns in that of Barry Egan, the socially anxious lead of one of the best Paul Thomas Anderson movies.

The film sees Barry fall for his sister’s co-worker (Emily Watson) while trying to fend off ‘The Mattress Man’ (the late Phillip Seymour Hoffman), who runs a local phone sex line that Barry has been phoning.

On paper, it had ‘strange’ written all over it. Still, thanks to Anderson’s remarkably heartfelt, contemplative, and wistful, it’s one of the best films of the last two decades and arguably Anderson’s shining achievement.

Think we got the list right? Let us know or if you want more hot takes check out our list of the best Spike Lee movies.