The 15 Best Adam Sandler Movies, Ranked

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For most comedians, getting fired from "Saturday Night Live" would be a career-killer. Yet for Adam Sandler, it opened the door to him becoming one of Hollywood's most bankable leading men. With "Billy Madison," "Happy Gilmore," "The Waterboy," and "The Wedding Singer," Sandler brought his singular brand of absurdist comedy to movie theaters everywhere. Although popular with audiences, these weren't exactly critical faves, and Sandler became something of a pariah to highbrow cineastes.

That all changed with "Punch-Drunk Love," directed by the patron saint of cinephiles, Paul Thomas Anderson. Rather than completely abandon his roots after his critical breakthrough, though, Sandler has jumped back-and-forth between subtle turns in art house fare and classic Happy Madison comedies. As his reputation amongst serious moviegoers has grown more positive, a critical reassessment of his earlier works has taken place, and the seeds of his dramatic work can be traced back to his goofiest performances. There are few people who can boast both six Razzies and an Independent Spirit Award, yet such is the career of the Sandman. Here are the 15 best Adam Sandler movies, ranked.

"The Waterboy" was inspired by one of Adam Sandler's "Saturday Night Live" characters, Canteen Boy, a water-loving boy scout who appeared in an infamous sketch with Alec Baldwin's predatory scoutmaster. "You could compare him to 'Canteen Boy,' whereas he does love water and they both get picked on a lot," Sandler explained in a 1998 CNN interview tied to the movie's release. "But the thing I like the most about this character is just that he is a genuine, good person." Audiences loved him too, and the absurdist comedy grossed $190 million worldwide.

Sandler plays Bobby Boucher, the 31-year-old waterboy for the University of Louisiana's football team. Emotionally stunted by his overbearing Mama (Kathy Bates), Bobby discovers a secret talent for tackling when his rage is unleashed. Although Coach Klein (Henry Winkler) wants Bobby to join the team, Mama forbids it, because football (or "foozball") is "The Devil." But with the help of his new girlfriend Vicky (Fairuza Balk), Bobby fulfills his destiny.

Cast: Adam Sandler, Kathy Bates, Fairuza Balk, Jerry Reed, Henry Winkler

Director: Frank Coraci

Rating: PG-13

Runtime: 90 minutes

Where to watch: Hulu

"Anger Management" was released the year after "Punch-Drunk Love," showing that Adam Sandler wasn't going to fully leave his comedy roots behind in pursuit of loftier artistic pursuits. In many ways, it's the flip side of that more dramatic turn, as it further examines the boiling rage lurking beneath Sandler's nice guy persona. Only this time, it's explored in a proper Happy Madison production, complete with lots of silly gags and celebrity cameos (including one by former New York City mayor Rudy Giuliani).

After a mild confrontation on an airplane turns into a full-blown meltdown, mild-mannered Dave Buznik is ordered to take anger management classes with Dr. Buddy Rydell (Jack Nicholson). Dr. Rydell has some unconventional therapy techniques, and before long he's invading all aspects of Dave's life, especially his relationship with his girlfriend, Linda (Marisa Tomei). Pairing Sandler with Nicholson turns out to be a match made in comedy heaven, as each one-ups the other with their wild-man antics.

Cast: Adam Sandler, Jack Nicholson, Marisa Tomei, Luis Guzmán, Woody Harrelson, John Turturro

Director: Peter Segal

Rating: PG-13

Runtime: 106 minutes

Where to watch: Hulu

Adam Sandler's Netflix deal might have started out with his biggest critical dud (the 0% Rotten Tomatoes scoring "The Ridiculous 6"), but it's also yielded some of his best films, including "Murder Mystery," which spawned a 2023 sequel. Sandler plays Nick Spitz, a New York City cop taking a long-promised European vacation with his wife, Audrey (Jennifer Aniston). While on their transcontinental flight, they meet a charismatic billionaire (Luke Evans) who invites them to his uncle's (Terence Stamp) wedding aboard a yacht. When the groom is murdered, the Spitzes are forced to become amateur detectives.

"Murder Mystery" is kind of like a Happy Madison version of the "Thin Man" series, which starred William Powell and Myrna Loy as high society sleuths Nick and Nora Charles. It's also one of the best Sandler vacation movies, i.e. movies with plots that allowed the Sandman to take a trip with his comedy friends. And just like a good vacation, "Murder Mystery" is a lot of fun.

Cast: Adam Sandler, Jennifer Aniston, Luke Evans, Terence Stamp, Gemma Arterton

Director: Kyle Newacheck

Rating: PG-13

Runtime: 97 minutes

Where to watch: Netflix

Having made one of the best Hanukkah movies with the animated "Eight Crazy Nights," Adam Sandler created a spooky season classic with "Hubie Halloween." Released on Netflix, it centers on yet another Sandler man-child, Hubie Dubois, who's the target of endless ridicule by the residents of Salem, Massachusetts. When October 31 rolls around, Hubie volunteers as the town's Halloween Helper. Only this year, a real-life murder investigation forces Hubie to become the hero Salem needs.

In his review for USA Today, Brian Truitt likened "Hubie Halloween" to "a mini Baby Ruth candy bar in a trick-or-treat bag: sweet, gooey, nutty and satisfying enough." And that's pretty much a ringing endorsement for the film, which doesn't attempt to rewrite the rules, but rather delivers on what Sandler fans have come to expect from a Happy Madison production: Tons of silly gags and lots of heart. It's perfect viewing for anyone who'd rather stay at home instead of trick-or-treat.

Cast: Adam Sandler, Kevin James, Julie Bowen, Ray Liotta, Rob Schneider, June Squibb, Steve Buscemi

Director: Steven Brill

Rating: PG-13

Runtime: 103 minutes

Where to watch: Netflix

In "Click," Adam Sandler plays Michael Newman, an architect who would like to spend less time at work and more time at home with his wife (Kate Beckinsale) and kids. He meets an inventor (Christopher Walken) who gifts him a magic TV remote that can control the universe. Hoping to fast-forward through life's boring chapters in order to get to the good stuff quicker, Michael soon learns he must appreciate every moment he's given, even the parts he'd like to skip.

Lurking beneath every Sandler comedy is a sentimental heart of gold, and most end with some life lesson affirming the importance of family and friends. That's the case with "Click," which functions as a sort of "It's a Wonderful Life" remake tinged with Happy Madison absurdity. It also holds a special place in Sandler's filmography, as it's the first (and so far, only) film he's made that earned an Oscar nomination (for best makeup, which it lost to "Pan's Labyrinth"). 

Cast: Adam Sandler, Kate Beckinsale, Christopher Walken, Henry Winkler, David Hasselhoff, Julie Kavner, Sean Astin

Director: Frank Coraci

Rating: PG-13

Runtime: 107 minutes

Where to watch: Tubi

Adam Sandler's love of basketball runs so deep that's he's often seen at public events wearing shorts better suited for the court than the red carpet. He put that passion to good use in "Hustle," for which he earned his first SAG nomination as best actor. He plays Stanley Sugarman, a down-on-his-luck talent scout who dreams of becoming a coach. While in Spain, he comes across Bo Cruz (real life NBA player Juancho Hernangómez), who's got a real talent for street ball. Thinking he has what it takes to go pro, Stanley brings Bo back to the U.S., and starts his path towards redemption.

"Hustle" was one of Sandler's best reviewed Netflix efforts, which might be faint praise considering that includes "The Do-Over" and "Sandy Wexler." "If he [Sandler] keeps working this hard, the same man who once symbolized Netflix's commitment to mediocrity could eventually turn out to be the streamer's greatest draft pick," raved David Ehrlich of Indiewire.

Starring: Adam Sandler, Queen Latifah, Juancho Hernangómez, Ben Foster, Robert Duvall

Director: Jeremiah Zagar

Rating: R

Runtime: 118 minutes

Where to watch: Netflix

The majority of Adam Sandler movies center on an over-grown man child who's dragged kicking and screaming into adulthood. That's poignantly explored in "Big Daddy," one of the Sandman's earliest attempts at adding pathos to his humor. He plays Sonny Koufax, a 32-year-old slacker who's desperate to prove he's an adult when his girlfriend (Kristy Swanson) breaks up with him. To prove his maturity, he agrees to take care of his roommate's (Jon Stewart) long-lost son, Julian (Cole Sprouse and Dylan Sprouse), who shows up at their apartment after his mom dies of cancer. Although his ex remains unimpressed, Sonny continues taking care of Julian when he learns he'll be put in foster care.

Although Sandler won the Razzie for worst actor, his performance in "Big Daddy" points the way towards his more grounded dramatic work. In fact, Paul Thomas Anderson is an avowed fan of the movie, which undoubtedly led to him casting Sandler in "Punch-Drunk Love."

Cast: Adam Sandler, Joey Lauren Adams, Jon Stewart, Rob Schneider, Cole Sprouse, Dylan Sprouse, Leslie Mann

Director: Dennis Dugan

Rating: PG-13

Runtime: 93 minutes

Where to watch: Netflix

Although they've only done three films together, Drew Barrymore is one of Adam Sandler's most important artistic collaborators (along with, of course, Rob Schneider). The movies the two made together range from the heights of "The Wedding Singer" to the lows of "Blended," with "50 First Dates" sitting comfortably in the middle. Sandler plays Henry Roth, a Hawaiian marine veterinarian who falls in love with art teacher Lucy Whitmore (Barrymore). But their relationship is complicated by Lucy's short-term memory loss, which causes her to forget the previous day's events every morning after she wakes up.

In many ways, the premise of "50 First Dates" is unresolvable, and should have failed at the idea stage. Yet it succeeds in spite of that, thanks in large part to the chemistry between Sandler and Barrymore. As per usual with the Sandman, there's a gooey center at the movie's heart, and it's sweet to watch the extreme lengths Henry goes to in order to win Lucy's heart over and over again. 

Cast: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Dan Aykroyd

Director: Peter Segal

Rating: PG-13

Runtime: 99 minutes

Where to watch: Netflix

Adam Sandler has filmed a number of standup specials in recent years, perhaps making up for the fact that he didn't have any prior to landing his job at "Saturday Night Live." That makes his performance in "Funny People," Judd Apatow's ambitious, shaggy, and touching dramedy, all the more affecting. In many ways, "Funny People" serves as a treatise to Sandler's entire career, examining his life as a comedian, a movie star, and as a man.

Sandler plays George Simmons, a comedy mega-star who's diagnosed with terminal cancer. Faced with his own mortality, he returns to the standup circuit, and hires an aspiring young comic (Seth Rogen) to be his joke writer. When he learns his cancer is in remission, he decides to make things right with his long-lost love (Leslie Mann), who's happily married with kids. Like the best work of James L. Brooks (who Sandler worked with on "Spanglish"), "Funny People" finds humor in pain, and pathos in comedy.

Cast: Adam Sandler, Seth Rogen, Leslie Mann, Eric Bana, Jonah Hill, Jason Schwartzman

Director: Judd Apatow

Rating: R

Runtime: 146 minutes

Where to watch: Max

After a handful of supporting turns in movies like "Airheads" and "Mixed Nuts," Adam Sandler became a bonafide leading man with "Billy Madison." He plays the titular dimwitted hotel heir whose father (Darren McGavin) is fed up with his loafing ways. The senior Madison forces his son to go back to school ... well, actually, go to school for the first time, since he was able to get out of it thanks to his dad's money. If Billy can't make his way from first grade through 12th in 24 weeks, he'll lose control of his family empire to his dad's conniving vice president, Eric Gordon (Bradley Whitford).

With a script by Sandler and Tim Herlihy, "Billy Madison" is the first instance of the Sandman crafting a film to his unique sensibilities. The themes and motifs that would define his career are all here: The immature man-child, the surreal gags, and the bizarre supporting players. Sandler's career was off and running with a box office hit.

Cast: Adam Sandler, Bradley Whitford, Josh Mostel, Bridgette Wilson, Norm Macdonald, Darren McGavin

Director: Tamra Davis

Rating: PG-13

Runtime: 89 minutes

Where to watch: Peacock

On a pure joke-by-joke basis, "Happy Gilmore" might be Adam Sandler's funniest comedy. It's his most revealing, in that it brings to the surface the rage that's boiling beneath many of his characters. Although his name denotes joy, hockey player Happy Gilmore (Sandler) is actually quite angry, especially about his inability to skate. When his grandmother (Frances Bay) is faced with eviction, he turns to professional golfing to raise enough money to pay off her mortgage. With the help of his one-handed trainer, Chubbs (Carl Weathers), and his girlfriend, Virginia (Julie Bowen), Happy channels his rage into a golf swing powerful enough to defeat Shooter McGavin (Christopher McDonald).

"Happy Gilmore" features some of Sandler's best gags, most famously a fist fight between him and "The Price is Right" host Bob Barker. But there's also a lot of insight into his screen persona, the developmentally-stunted adult who's both sweet and incredibly volatile. Those twin poles exist beautifully in his best roles, of which Happy Gilmore is certainly one.

Cast: Adam Sandler, Christopher McDonald, Julie Bowen, Carl Weathers

Director: Dennis Dugan

Rating: PG-13

Runtime: 92 minutes

Where to watch: Amazon Prime

For a movie that features multiple Oscar winners, Adam Sandler is the clear standout of Noah Baumbach's "The Meyerowitz Stories (New and Selected)." He plays Danny Meyerowitz, who's just moved back in with his father, sculptor and retired professor Harold (Dustin Hoffman), and his hippie wife, Maureen (Emma Thompson), after a messy divorce. His brother, successful financier Matthew (Ben Stiller), and their sister, Jean (Elizabeth Marvel), return home for a retrospective of their dad's work. But when Harold suffers a fall, his three children are suddenly faced with the prospect of his permanent departure.

As per usual with Baumbach, "The Meyerowitz Stories" is smart, sharp, and very prickly. Sandler is the film's beating heart as a man who's been deeply wounded by his overbearing father, and is desperately trying to avoid inflicting that same damage on his daughter, Eliza (Grace Van Patten). It's yet another example of the Sandman stretching beyond the broad comedy that made him famous.

Cast: Adam Sandler, Ben Stiller, Dustin Hoffman, Emma Thompson, Elizabeth Marvel

Director: Noah Baumbach

Rating: TV-MA

Runtime: 112 minutes

Where to watch: Netflix

Of all of Adam Sandler's early films, "The Wedding Singer" is his most effective blending of wacky comedy and heart-on-its-sleeve sentimentality. It's also perhaps the one that's been most successfully reclaimed as a classic, even spawning a Tony-nominated Broadway musical. It shouldn't be surprising that it lends itself so well to the stage, since it's essentially a modern day Fred Astaire/Ginger Rogers movie, made through a Happy Madison lens.

Set in 1985, it stars Sandler as Robbie Hart, a New Jersey wedding singer who's left at the alter by his fiancee, Linda (Angela Featherstone). He soon finds himself falling in love with Julia Sullivan (Drew Barrymore), a kind waitress who's engaged to bond investor Glenn Gulia (Matthew Glave). Although he's agreed to sing at her wedding, Robbie plans to win her heart instead. You can see exactly where "The Wedding Singer" is headed from the moment Sandler and Barrymore are on screen together, but that doesn't mean we're not rooting for them to get there.

Cast: Adam Sandler, Drew Barrymore, Christine Taylor

Director: Frank Coraci

Rating: PG-13

Runtime: 97 minutes

Where to watch: Peacock

When Adam Sandler made "Punch-Drunk Love," the general critical perception was that it was a stunning change of pace. Yet the brilliance of Paul Thomas Anderson's art house hit is that it is, at its core, an Adam Sandler movie, albeit a deeper and more perceptive one. Sandler plays Barry Egan, a sad, lonely man who lashes out in shocking bursts of violence. He falls in love with the angelic Lena Leonard (Emily Watson), and tries to rack up enough frequent-flier miles from a Healthy Choice foods promotion to meet her in Hawaii. But their romance is threatened by phone sex scammers led by mattress salesman Dean Trumbell (Philip Seymour Hoffman).

"Given a director and a screenplay that sees through the Sandler persona, that understands it as the disguise of a suffering outsider, Sandler reveals depths and tones we may have suspected but couldn't bring into focus," wrote Roger Ebert of the film, which earned Sandler his first Golden Globe nomination.

Cast: Adam Sandler, Emily Watson, Philip Seymour Hoffman, Luis Guzmán

Director: Paul Thomas Anderson

Rating: R

Runtime: 95 minutes

Where to watch: Amazon Prime

Who would've guessed that 20 years after winning a Razzie for "Big Daddy," Adam Sandler would be an Independent Spirit Award winner for "Uncut Gems"? Yet such was the inevitable career trajectory for a man whose filmography has encompassed both reviled box office hits and acclaimed art house fare. Sandler plays Howard Ratner, a jeweler in New York's Diamond District who's deeply in debt from making big bets on basketball games (he does love the game). He thinks he's found a way out with a rare black opal, which he hopes will garner him enough money to pay off his loan shark brother-in-law (Eric Bogosian). As his problems continue to stack up, Howard digs himself deeper into his self-made hole.

Oliver Jones of The Observer called "Uncut Gems," "the fullest expression of Sandler and his singular talents that we have witnessed in his sometimes confounding and often infuriating 30-plus-year career," summarizing the love-hate relationship the Sandman has enjoyed with critics.

Cast: Adam Sandler, LaKeith Stanfield, Julia Fox, Kevin Garnett, Idina Menzel, Eric Bogosian

Directors: Josh Safdie, Benny Safdie

Rating: R

Runtime: 135 minutes

Where to watch: Amazon Prime