10 Adam Sandler Movies (Almost) as Funny as Happy Gilmore

Adam Sandler’s filmography is far more diverse than his early reputation suggests. Known for crafting hilarious stories that balance absurdist humor with genuine heart, his best comedies often deliver goofy slapstick, heartfelt romance, satisfying emotional arcs, and an ever-present theme of unlikely redemption. While Happy Gilmore remains a fan favorite (despite its recent underwhelming sequel) and arguably one of his most iconic performances, several other films have come remarkably close in comedic power, emotional resonance, and lasting pop culture relevance.

With each new entry, Sandler continues to redefine the boundaries of mainstream comedy. His ability to blend absurdity with deeply personal themes—often within the same scene—has made him a singular voice in American comedy. Beyond his consistent collaborations and outlandish characters lies an artist willing to evolve, experiment, and connect with his audience in unexpected ways. His most beloved films (some by fans, some by critics) stand out not just for their laughs, but for the way they reflect Sandler’s ongoing creative range.

Hubie Halloween is a Quirky, Off-Brand Horror Spoof

Hubie Halloween is Available to Stream on Netflix

In a surprising late-career twist, Sandler returned to his absurd roots with Hubie Halloween, a genre-blending comedy-horror film that brings spooky vibes and slapstick laughs in equal measure. Sandler plays Hubie Dubois, a well-meaning but socially mocked man in Salem, Massachusetts, who finds himself at the center of a Halloween mystery. The film pokes fun at horror tropes while offering sincere moments of redemption and community. Despite its streaming release, it became a seasonal hit on Netflix and proved that Sandler still has the ability to surprise and charm audiences decades into his career.

What sets Hubie Halloween apart from other late-period Sandler movies is its reverence for the Halloween genre and its surprisingly strong emotional core. It blends the juvenile with the nostalgic, featuring cameos from Sandler regulars and even a reunion with his Happy Gilmore co-star, Julie Bowen. Despite the absurd humor and over-the-top antics, the film manages to capture the warmth of a heartfelt community comedy.

Grown Ups is the Quintessential Sandler Movie

Grown Ups is Available to Stream on Netflix

Starring a powerhouse comedic ensemble including Chris Rock, Kevin James, David Spade, and Rob Schneider, Grown Ups revolves around childhood friends reuniting after their basketball coach’s death. The plot is far from innovative, but that’s not the point. The movie thrives on chemistry, inside jokes, and the easy banter between friends who’ve known each other forever—both on-screen and off. With themes of family, nostalgia, and letting go of ego, Grown Ups is both a crowd-pleaser and a reminder of the importance of lifelong friendship. The inclusion of the late Cameron Boyce adds an extra emotional touch.

Its sequel may have muddied its legacy with more exaggerated gags, but the original Grown Ups has a sincerity that remains endearing. It’s a portrait of middle-aged friendship that doesn’t rely on melodramatic storytelling but instead on good vibes and low-stakes antics. It may not be a critical darling, but it’s a comfort watch that feels like a family reunion.

Grown Ups

Release Date

June 24, 2010

Runtime

102 Minutes

Director

Dennis Dugan

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  David Spade

  Marcus Higgins

Just Go With It is a Charmingly Chaotic, Unromantic Rom-Com

Just Go With It is Available to Stream on Hulu

Sandler and Jennifer Aniston team up in this romantic comedy about a plastic surgeon who convinces his assistant to pose as his estranged (and soon-to-be-divorced) wife to cover up a lie he told his girlfriend. What follows is a vacation full of chaos, misunderstandings, and unexpected revelations. The chemistry between Sandler and Aniston is undeniable, and the child actors manage to steal almost every scene. Nicole Kidman even shows up in a hilariously unexpected supporting role. While critics were mixed, the film was a box office success and has since become one of Sandler’s most beloved comedies.

The escapist appeal of Just Go With It lies in its picture-perfect setting and its accidental romanticism. It’s a movie that fully embraces its premise, no matter how implausible (though very), and leans into its fantasy to deliver a story that’s both funny and oddly sincere. Sandler and Aniston’s chemistry only elevates this already magnetic narrative, and the film’s humor ranges from laugh-out-loud slapstick to sweet, grounded moments.

Just Go With It

Release Date

February 11, 2011

Runtime

117minutes

Director

Dennis Dugan

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The Wedding Singer is a Heartwarming Nostalgia-Filled Classic

The Wedding Singer is Available to Stream on Tubi

This retro romantic comedy pairs Sandler with Drew Barrymore for the first time, and their chemistry is pure unexpected magic. Set in the 1980s, the film follows Robbie Hart, a wedding singer recovering from a broken heart who finds hope and love again in the most unexpected of places. Barrymore’s sweetness and Sandler’s underdog vulnerability create a warm, hilarious dynamic that carries the film through its musical numbers and rom-com tropes.

The Wedding Singer succeeds because it marries nostalgia with sincerity. The costumes, soundtrack, and set design scream ’80s, but the emotional core is timeless. It’s one of the best examples of Sandler playing a character who’s not just funny but deeply empathetic, making it a standout in his romantic comedy catalog.

The Wedding Singer

Release Date

February 13, 1998

Runtime

97 Minutes

Director

Frank Coraci

Writers

Tim Herlihy

Little Nicky is a Star-Studded, Absurd Fever Dream

Little Nicky is Available to Stream on Pluto TV

One of Sandler’s strangest films, Little Nicky is a dark comedy set in a world where the son of Satan comes to Earth to retrieve his evil brothers who’ve escaped from Hell. Featuring a bizarre array of cameos—from Quentin Tarantino to the late Ozzy Osbourne—the movie embraces its weirdness and leans into surrealist comedy. Sandler’s performance is unlike anything else in his filmography, channeling a bizarre mix of vulnerability and absurdity. The film flopped upon release but has since developed a devoted cult following for its unapologetic commitment to its outlandish concept.

Though divisive, Little Nicky remains one of the most visually distinct and daring Sandler comedies. With its blend of slapstick, religious satire, and insanely fantastical world-building, it may be a wild ride, but it’s a memorable one. It’s a film that dares to be strange—and in that strangeness lies its charm.

Little Nicky

Release Date

November 10, 2000

Runtime

90 minutes

Director

Steven Brill

Writers

Tim Herlihy, Adam Sandler, Steven Brill

Murder Mystery is a Flawless Whodunnit Satire

Murder Mystery is Available to Stream on Netflix

Reuniting with Aniston once again, Sandler takes on the world of whodunnits in Murder Mystery, a fast-paced satire of Agatha Christie-style mysteries. Playing a New York cop and his hairdresser wife who get tangled in a lavish European murder case, the duo navigates a world of eccentric aristocrats, deceit, and straight-up tomfoolery. The absurdity of the plot and the film’s nonstop chaos make for perfect comedy fuel, and the chemistry between the leads grounds the craziness. With action, romance, and some unexpected twists, the movie was a massive hit on Netflix and even earned a sequel, though the original remains superior.

What makes Murder Mystery particularly delightful is its self-awareness. The film pokes fun at every trope in the murder-mystery handbook while never fully veering into parody (very à la Scream). It walks a fine line between genuine suspense and absurdist comedy, making it a versatile crowd-pleaser that’s smarter than it looks at first glance.

Murder Mystery

Release Date

June 14, 2019

Runtime

97minutes

Director

Kyle Newacheck

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50 First Dates is a Sweetly Ironic Romantic Gem

50 First Dates is Available to Stream on Netflix

Reuniting with Barrymore, Sandler delivers one of his most heartfelt performances in 50 First Dates. This romantic comedy follows a man trying to win the heart of a woman who forgets him every day due to short-term memory loss. The Hawaii setting, loveable side characters (including a hilarious performance by Rob Schneider), and genuinely emotional premise make it both one of Sandler’s funniest and most touching films.

What elevates 50 First Dates is its commitment to emotional depth. Beneath the jokes lies a story about patience, acceptance, and the persistence of love. Sandler’s usual goofiness is tempered with a genuine tenderness that makes the film resonate long after the credits roll. Plus, the comedic situations prompted by the premise are not only endless, but priceless.

50 First Dates

Release Date

February 13, 2004

Runtime

99minutes

Director

Peter Segal

Mr. Deeds is a Painfully Underrated Sandler Classic

Mr. Deeds is Available to Stream on FuboTV

A remake of the 1936 film Mr. Deeds Goes to Town, this modern entry sees Sandler play a small-town guy who inherits a massive corporate empire out of the blue. Opposite Winona Ryder’s undercover reporter, Sandler mixes sweet naivety with unhinged fury in a fish-out-of-water tale that veers between sweet, goofy, and sharp satire. John Turturro’s scene-stealing turn as the loyal butler Emilio (along with Sandler’s recurring hideous foot gag) is worth the price of admission alone.

While critics were divided, audiences responded warmly to Mr. Deeds. It encapsulates Sandler’s brand of comedic idealism, where kindness and sincerity eventually triumph over cynicism. It’s a comforting fairy tale for the modern age, with just enough edge to keep it fresh, and just enough charm to get past some of its implausible plot points.

Mr. Deeds

Release Date

June 28, 2002

Runtime

96 minutes

Director

Steven Brill

Anger Management is a Bizarrely Unhinged Masterpiece

Anger Management is Available to Stream on Tubi

Starring opposite Jack Nicholson, Anger Management sees Sandler as an (extremely) mild-mannered man forced to confront his repressed rage under the guidance of an unorthodox therapist. The film’s premise alone sets the stage for chaos, and Nicholson’s unhinged performance as the cooky therapist makes it impossible to look away. The dynamic between the two stars is a riot—Sandler’s slow burns and Nicholson’s unpredictable energy fuel some of the funniest scenes in Sandler’s career.

Beneath the antics, Anger Management is about self-awareness and personal growth. Its final act delivers a clever twist that recontextualizes much of the movie, proving that even in his most chaotic stories, Sandler often has something surprisingly profound to say. Underneath all those goofy gags always hides an overlooked thematic richness that deserves a second take.

Big Daddy is a Heartfelt Adult Coming-Of-Age Flick

Big Daddy is Available to Stream on Netflix

At its heart, Big Daddy is a classic story about a man growing up by raising someone else. When Sandler’s slacker character takes in a young boy (played by Dylan and Cole Sprouse), what begins as a scheme to impress a girlfriend turns into a heartfelt journey of unexpected parenthood. Balancing hilarious scenarios—like teaching a kid to pee on a wall—with genuine emotional beats, Big Daddy showcases the full spectrum of Sandler’s comedic and dramatic range.

This film resonated with both audiences and critics, becoming one of Sandler’s highest-grossing and most beloved movies (and most recently, a streaming hit). It remains a benchmark for what makes his comedies so enduring: outrageous setups anchored by heart, connection, and growth. His characters tend to be flawed yet charming, and the comedy he injects into his missteps makes his character growth even more compelling and satisfying to witness.

Big Daddy

Release Date

June 25, 1999

Runtime

93 Minutes

Director

Dennis Dugan