Adam Sandler Movies Ranked: 10 Best, From Big Daddy to Uncut Gems

No comedian of his generation has split opinion quite like Adam Sandler. The Adam Sandler movies counted down here cover both halves of a strange and fascinating career: the loud, quotable comedies he made after leaving Saturday Night Live, and the handful of dramatic roles that proved the man-child persona was hiding a serious actor all along. Sandler has worked with Paul Thomas Anderson, Noah Baumbach and the Safdie brothers, yet he has never abandoned the friends and directors who helped him make his name in the 1990s.

Performances come first in the ordering, and the film around them second. That means a ferocious dramatic turn in an anxious crime story can sit above a beloved comedy, and a supporting part in a quiet family drama can beat a bigger, broader hit. Each pick names his character, the director and the co-stars who matter most, so the countdown also works as a map of the people who brought out the best in him. It starts at tenth place and climbs to the role that nobody who saw his early films could have predicted.

Adam Sandler Movies Ranked With Roles and Directors

10. Big Daddy (1999)

Dennis Dugan's Big Daddy casts Sandler as Sonny Koufax, a law-school graduate in his thirties who works one day a week in a toll booth and has no plans to grow up. When a five-year-old boy named Julian, played by Cole Sprouse, turns up at his door, Sonny takes him in, partly to win back his girlfriend. Jon Stewart plays Kevin, Sonny's roommate, whose own connection to the boy drives much of the plot, and Joey Lauren Adams plays Layla, a lawyer who sees there is more to Sonny than his slacker routine.

It is a classic Sandler setup, an overgrown kid forced into responsibility, and the jokes about teaching a child bad habits are as broad as you would expect. What saves it is the bond between Sonny and Julian, which Sandler plays with real tenderness by the courtroom finale. It ranks tenth because its pleasures are familiar and its plotting is loose. Still, it shows the formula at its most heartfelt and marks the moment his comedies started leaning into family stories, a direction that carried through much of his later work.

9. Click (2006)

Frank Coraci's Click gives Sandler a high-concept fantasy. He plays Michael Newman, an overworked architect who never has enough time for his wife and children. When he goes shopping for a universal remote control, a strange salesman named Morty, played by Christopher Walken, gives him one that controls his life, letting him pause, rewind and fast-forward through anything he would rather skip. Kate Beckinsale plays his wife Donna, and David Hasselhoff plays Ammer, the self-absorbed boss whose promotions Michael keeps chasing. The device soon starts making choices for him.

Click begins as a broad comedy and becomes surprisingly sad, as Michael realises how much of his family's life he has missed. Sandler handles that turn better than the script deserves, and the later scenes, played under heavy ageing make-up, carry real feeling. It ranks ninth because the jokes in the first half are crude and forgettable. What lifts it is the performance in the final stretch, which hints at the dramatic actor he would become, and its blend of fantasy and family drama is unusual among his comedies.

8. The Meyerowitz Stories (New and Selected) (2017)

Noah Baumbach's The Meyerowitz Stories (New and Selected) is a family comedy about adult children and their difficult father. Sandler plays Danny Meyerowitz, a recently separated, out-of-work musician with a bad hip who moves back in with his father as his daughter heads off to college. Dustin Hoffman plays Harold, a prickly sculptor who never received the recognition he believes he deserved, Ben Stiller plays Danny's more successful half-brother Matthew, and Emma Thompson plays Harold's eccentric wife Maureen. Old grudges surface as Harold's health declines.

This is the most understated work Sandler has done. Danny is a man who has spent his life being overlooked, and Sandler lets that hurt seep out through jokes, awkward hugs and the occasional burst of temper that recalls his comic persona in a sadder key. His scenes with Stiller, two brothers who love and resent each other in equal measure, are the heart of the film. It ranks eighth because Danny shares the spotlight with a large ensemble, but it remains a fine example of how well he fits into an actor's film.

7. 50 First Dates (2004)

Peter Segal's 50 First Dates reunites Sandler with Drew Barrymore on the islands of Hawaii. He plays Henry Roth, a marine-park veterinarian who avoids commitment by dating only tourists. Then he meets Lucy Whitmore, a local woman who lost her short-term memory in a car accident and wakes up each morning believing it is the same day. To win her, Henry has to make her fall for him again and again. Rob Schneider plays Henry's friend Ula, and Sean Astin plays Doug, Lucy's protective brother, who helps the family recreate her day.

The premise could have been grim, but Sandler and Barrymore turn it into something sweet and often moving, especially as Henry starts to think about what love means when the other person cannot remember it. Sandler is gentler here than in almost any of his comedies, and his best scenes are the small ones where Henry patiently retells their story. It ranks seventh because the broad side gags have aged badly. The central performance, though, is among his warmest, and the ending lands better than it has any right to.

6. Billy Madison (1995)

Tamra Davis directed Billy Madison, the film that turned Sandler from a sketch performer into a movie star. He plays Billy, the pampered adult son of a hotel tycoon, who spends his days drinking by the pool. To prove he deserves to inherit the family company, Billy agrees to repeat every grade from first through twelfth, two weeks at a time. Bradley Whitford plays Eric Gordon, the scheming executive who wants the business for himself, Bridgette Wilson plays Veronica Vaughn, the teacher Billy falls for, and Josh Mostel plays Principal Max Anderson.

It is wildly uneven and gloriously silly, and it remains one of the most quotable comedies of the decade. Sandler's commitment to Billy's babyish voice, sudden tantrums and odd non sequiturs set the template for a decade of hits. The film ranks sixth because later comedies polished the formula, but none of them feel as raw or as gleefully strange. As a starting point for his career, it is essential viewing, and it explains everything about the persona he would later deconstruct.

5. Hustle (2022)

Jeremiah Zagar's Hustle casts Sandler as Stanley Sugerman, a weary international scout for the Philadelphia 76ers who has spent years on the road dreaming of a coaching job. On a trip to Spain he spots Bo Cruz, a raw but brilliant street player portrayed by real NBA forward Juancho Hernangómez, and risks his career to bring him to America for the draft. Queen Latifah plays Teresa, Stanley's patient wife, and Ben Foster plays Vince Merrick, the team executive who would happily see him fail.

Sandler has rarely seemed so relaxed on screen. Stanley is funny, tired and kind, and the actor plays him with obvious affection for the game, which gives the training montages and family scenes a lived-in warmth. The film follows a familiar sports-drama shape, so it never quite reaches the heights of the films ranked ahead of it, but within that shape it is beautifully done. Fifth place reflects how complete the performance is: Hustle is the best example of the grown-up, low-key Sandler that emerged in the later part of his career.

4. The Wedding Singer (1998)

Frank Coraci's The Wedding Singer is set in 1985 and stars Sandler as Robbie Hart, a sweet-natured performer who sings at other people's weddings until his own fiancée leaves him standing at the altar. Heartbroken, he befriends Julia Sullivan, a waitress played by Drew Barrymore, who is engaged to a wealthy and unfaithful jerk. Christine Taylor plays Julia's cousin Holly, and Allen Covert plays Robbie's friend Sammy. The movie is soaked in the fashions and music of the decade, from shoulder pads to synth pop, and plays its nostalgia for laughs.

This is the film that first revealed Sandler's romantic side, and his pairing with Barrymore is still one of the most charming partnerships of 1990s comedy. Robbie is gentle where Happy and Billy are brats, and Sandler shows he can play heartbreak, including a memorably bitter song performed at a reception. It lands fourth because the chemistry is real and the jokes still work. It also set the template for the warmer Sandler that followed and sits comfortably among the best romance movies built on comedy.

3. Happy Gilmore (1996)

Dennis Dugan's Happy Gilmore stars Sandler as a failed hockey player with a vicious temper and a slapshot of a swing. When the taxman seizes his grandmother's house, Happy discovers he can drive a golf ball enormous distances and joins the professional tour to win the money back. Christopher McDonald plays Shooter McGavin, the smug golf star who resents the newcomer, Julie Bowen plays Virginia, the tour's public relations head who sees the good in him, and Frances Bay plays the sweet grandmother he is fighting for. Fistfights on the fairway follow.

This is the purest version of the Sandler comedy formula: a childish hero, explosive tantrums, an unlikely sport and a sweet streak under the noise. Plenty of his later comedies tried to repeat the trick and none matched it, mainly because Happy's anger feels so specific and his victories so earned. He even revisited the character in Happy Gilmore 2 (2025). Happy Gilmore ranks third because it is his funniest, tightest comedy, and the one that most defines how audiences of the 1990s saw him.

2. Punch-Drunk Love (2002)

Punch-Drunk Love was written and directed by Paul Thomas Anderson as a strange, tender romance built around Sandler's screen persona. He plays Barry Egan, a lonely small businessman who sells novelty toilet plungers, endures relentless teasing from his seven sisters and suffers sudden bursts of rage. Emily Watson plays Lena Leonard, a woman who quietly decides she likes him. Meanwhile a call to a phone line lands Barry in an extortion scheme run by Philip Seymour Hoffman's furious mattress salesman, Dean Trumbell, and Luis Guzmán plays Barry's employee Lance.

Anderson took the anger that powered Sandler's 1990s comedies and asked what it would feel like from the inside. The answer is a performance full of embarrassment, longing and odd, funny violence, and it earned Sandler a Golden Globe nomination for Best Actor in a musical or comedy. It ranks second because it was the first real proof of his range and remains the most original film he has starred in. Anyone who dismissed him as a one-note clown should start here, then watch the films ranked below it with fresh eyes.

1. Uncut Gems (2019)

Josh and Benny Safdie's Uncut Gems unfolds over a few frantic days in New York's Diamond District. Sandler plays Howard Ratner, a fast-talking jeweller and compulsive gambler who has smuggled in a rare black opal he plans to auction for a fortune. Before he can, he lends the stone to basketball star Kevin Garnett, playing himself, and the deal spirals while debt collectors close in. LaKeith Stanfield plays Demany, who steers wealthy clients to Howard's shop, and Julia Fox plays Julia, the employee and girlfriend Howard keeps in an apartment across town.

Nothing else in Sandler's career comes close to this. He takes the restless energy of his comedies and turns it into something unbearable to watch and impossible to look away from, a man who cannot stop placing bets even as every one threatens to destroy him. Howard is grating, needy and weirdly lovable, and Sandler never begs for pity. The film is a two-hour panic attack that belongs among the best thriller movies of its decade, and he is at the centre of every scene. Uncut Gems tops the ranking because it shows exactly what his talent can do when a director pushes it.

Honourable Mentions From Sandler's Filmography

These roles fell just outside the top ten but are worth knowing, whether you want more comedy or more of his dramatic side.

• Mr. Deeds (2002): As Longfellow Deeds, a small-town greeting card poet who inherits a media empire, he leans into his gentle everyman side.
• Anger Management (2003): Playing Dave Buznik, a meek office worker ordered into therapy, he turns his usual explosive persona inside out.
• The Longest Yard (2005): His Paul Crewe, a disgraced quarterback leading a prison football team, is a crowd-pleasing remake of the 1974 film.
• Hubie Halloween (2020): Hubie Dubois, a timid volunteer who keeps his town safe on Halloween night, is one of his most likeable late comic creations.
• Spaceman (2024): As Jakub Procházka, a lonely astronaut on a long solo mission, he gives one of his most introspective performances.

Comedy Sandler Versus Dramatic Sandler

His dramatic work claims the top two places in the ranking, but it would be a mistake to treat the comedies as lesser. The qualities that make Uncut Gems and Punch-Drunk Love so striking, the volatility, the childish need for approval, the tenderness that sneaks out sideways, were all present in Billy Madison and Happy Gilmore. What changed was the framing. Directors like Paul Thomas Anderson and the Safdie brothers stopped asking the audience to laugh at those traits and asked them to sit with the discomfort instead.

The comedies, in turn, depend on a skill that is easy to underrate: Sandler can make an obnoxious character sympathetic within a single scene. Happy Gilmore is rude to everyone, yet you root for him because of how he treats his grandmother. Robbie Hart and Henry Roth work for the same reason, flawed men made lovable by sincerity. Seen side by side, the comedies and the dramas tell one story about an actor who has always understood rage and sweetness as two sides of the same personality.

Frequently Asked Questions

What is Adam Sandler's best movie?

Uncut Gems (2019) takes first place here. As Howard Ratner, a gambling-addicted jeweller, Sandler gives the most intense and accomplished performance of his career.

Has Adam Sandler been nominated for a Golden Globe?

Yes. He was nominated for the Golden Globe for Best Actor in a musical or comedy for Punch-Drunk Love (2002), directed by Paul Thomas Anderson.

Which Adam Sandler movies co-star Drew Barrymore?

Sandler and Barrymore starred together in The Wedding Singer (1998), 50 First Dates (2004) and Blended (2014).

Is there a sequel to Happy Gilmore?

Yes. Sandler returned to the role in Happy Gilmore 2, released in 2025, nearly three decades after the original film.

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