10 Funniest Adam Sandler Movies, Ranked

Adam Sandler is one of those rare talents who makes movies hit after-hit-after-hit. While he has dabbled in drama and proven that he’s capable of pulling it off, comedy is where Sandler shines, both behind the camera and in front of it. He has come a long way since his career as a Saturday Night Live (SNL) cast member. And while many of his movies are panned by critics, they are often box office hits, even becoming cult classics.

There’s a trend when it comes to Sandler movies, which often center around silly, immature humor. He was in his prime in the ‘90s and early 2000s when he starred in (and produced) some of his most memorable comedy movies. But with one new movie cracking the top five on this list, it’s clear Sandler shows no signs of slowing down. He has plenty more funny movies to come to delight audiences, and sometimes confuse critics, as to their runaway success. Until those movies are released, let’s go back to the past and rank his funniest movies.

10 ‘Punch-Drunk Love’ (2002)

Directed by Paul Thomas Anderson

While Punch-Drunk Love is a departure from Sandler’s usual comedic style, the movie, which ranks among his best, is an absurdist romantic comedy-drama that ranks as one of his funniest. Sandler showed his versatility as an actor beyond silly comedy, playing Barry, a bachelor who lives a lonely life, often the subject of ridicule by his sisters. This has caused him to develop issues with anger and social anxiety. When he meets a beautiful woman named Lena (Emily Watson), however, Barry’s life is set to change as he tries to overcome his biggest hurdles.

An interesting mix of comedy with a heartwarming story about a man coming into his own, Punch-Drunk Love is praised for its uniqueness and touching moments that are beautifully juxtaposed with delightful comedy as well.

Punch-Drunk Love can be streamed on Hoopla in the U.S.

Watch on Hoopla

9 ‘Hotel Transylvania’ (2012)

Directed by Genndy Tartakovsky

In this animated monster comedy, Sandler voices the lead character Count “Drac” Dracula, a vampire running his own hotel and fiercely protecting his daughter Mavis (Selena Gomez). The hotel is designed as a place where monsters can relax outside the human world, unafraid to just be themselves. When he invites a big group to celebrate his daughter’s 118th birthday, however, things go awry when a human named Jonathan (Andy Samberg) shows up. He can’t let the others know lest it causes trouble and ruins his reputation as offering a safe haven for monsters, away from humans.

Hotel Transylvania is a rare Sandler film that is suitable to watch with the whole family. It’s silly but innocent fun without inappropriate jokes or potty humor meant for adults. It’s quirky, fun, and the type of movie kids will want to watch again and again.

Hotel Transylvania can be streamed on Prime Video in the U.S.

Rent on Prime

8 ’50 First Dates’ (2004)

Directed by Peter Segal

One of Sandler’s many collaborations with Drew Barrymore, the pair star together in this romantic comedy. Sandler is Henry, a womanizing man who falls for Lucy (Barrymore), an art teacher. But there’s a problem: she suffers from amnesia and every time she falls asleep and wakes up, she forgets who he is. This can also be viewed as an opportunity, however, since when Henry messes up, he has another chance at that pivotal “first date” the next day. And he takes all those chances.

Like Groundhog Day with dating as the central theme, 50 First Dates has the beautiful backdrop of Hawaii, making for a great date movie. The actors were praised for their on-screen chemistry. While the unique story might be tough to believe, it is fun, nonetheless. There are tons of comedic moments throughout, wrapped inside a touching love story.

50 First Dates can be streamed on Starz in the U.S.

Watch on Starz

7 ‘Leo’ (2023)

Directed by Robert Marianetti, Robert Smigel, David Wachtenheim

Another animated movie, Leo is as heartwarming as it is funny. At the center of the plot of the musical comedy is the titular character, voiced by Sandler, a tuatara who resides in a fifth-grade classroom as the class pet. Realizing he may only have a single year left in his typical 75-year lifespan, Leo tries to escape the clutches of a young girl who has taken him home for the weekend. But when she discovers that he can talk, she enlists his help and advice to make friends.

What continues is a touching relationship between the reptile and the various kids in the class who take him home from one weekend to the next. He becomes a confidant, of sorts, finding a greater purpose in his life than ever before. It sounds sappy, and it is. But Leo is also filled with hilarious moments, thanks to both the script and Sandler’s always engaging voice work. Combined with catchy tunes, Leo is a fun family watch.

Leo

Release Date

November 21, 2023

Cast

Adam Sandler , Bill Burr , Cecily Strong , Jason Alexander

Runtime

102 minutes

Writers

Robert Smigel , Adam Sandler , Paul Sado

Director

Robert Marianetti , Robert Smigel , David Wachtenheim

Leo can be streamed on Netflix in the U.S.

Watch on Netflix

6 ‘Mr. Deeds’ (2002)

Directed by Steven Brill

A remake of the 1936 movie Mr. Deeds Goes to Town, one of Frank Capra’s best, Sandler is Longfellow, a pizzeria owner whose life is upended when he discovers that he is the sole heir to a great uncle’s multi-billion dollar fortune. A hilarious fish-out-of-water story, Longfellow travels to New York with the intention of selling his shares in the company to businessman Chuck Cedar (Peter Gallagher) and moving on with his life. He meets a tabloid reporter named Babe (Winona Ryder) who poses as a school nurse to try and get dirt on him, but she ends up falling for him for real.

The twist at the end of the story brings all the drama and hilarity together beautifully. Mr. Deeds might have been universally panned by critics, but much like many of Sandler’s movies, it was a massive box office success. It’s a cute, feel-good story that features Sandler’s signature comedy and themes of the good guys winning in the end.

Mr. Deeds can be streamed on Prime Video in the U.S.

Rent on Prime

5 ‘You Are So Not Invited To My Bat Mitvah’ (2023)

Directed by Sammi Cohen

Starring Sandler’s real-life daughters and wife, You Are So Not Invited To My Bat Mitvah is a relatable coming-of-age comedy drama about a teenager excited about celebrating her pending Bat Mitvah. While she is looking forward to doing it alongside her best friend, as is typical at that age, a boy comes between them.

Receiving rave reviews, You Are So Not Invited To My Bat Mitvah might have raised eyebrows with Sandler casting his immediate family members. But both his daughters and wife held their own leading the cast. The level of humor comes from the perspective of an adolescent, and it’s one of Sandler’s movies where he lets someone else shine as the star and take the comedic reigns.

You Are So Not Invited to My Bat Mitzvah

Release Date

August 25, 2023

Cast

Idina Menzel , Adam Sandler , Jackie Sandler , Sadie Sandler , Sunny Sandler , Samantha Lorraine , Sarah Sherman

Runtime

103m

Main Genre

Comedy

Director

Sammi Cohen

You Are So Not Invited to My Bat Mitzvah can be streamed on Netflix in the U.S.

Watch on Netflix

4 ‘The Wedding Singer’ (1998)

Directed by Frank Coraci

As heartwarming and sweet as it is funny, The Wedding Singer is the second collaboration between Sandler and Barrymore to make the list. He’s Robbie, a wedding singer who is about to be married. But when he has a chance encounter with Julia (Barrymore), a waitress at one of the venues, sparks fly. Robbie knows there’s something about this girl, and his desire is solidified when he meets her fiancé, who happens to be an awful human and even worse partner.

The Wedding Singer has sad, more emotional and dramatic moments, but it’s the tenderness mixed with the humor that make for a winning combination. The Wedding Singer also ranks among the most rewatchable ‘90s rom-coms.

The Wedding Singer

Release Date

February 13, 1998

Cast

Adam Sandler , Drew Barrymore , Christine Taylor , Allen Covert , Matthew Glave , Ellen Albertini Dow

Runtime

95

Main Genre

Comedy

Writers

Tim Herlihy

Director

Frank Coraci

Studio

New Line Cinema

The Wedding Singer can be streamed on Prime Video in the U.S.

Rent on Prime

3 ‘Big Daddy’ (1999)

Directed by Dennis Dugan

Another comedy from Sandler that showcases his ability to combine heartwarming, touching stories with comedy, Big Daddy follows his typical fish-out-of-water scenario. His roommate Kevin (Jon Stewart) apparently fathered a child the mother can no longer care for. When she drops the little boy Julian (Dylan and Cole Sprouse) off at their doorstep, Sonny (Sandler) has no choice but to care for him, since Kevin is away in China on business.

The story follows the unlikely pair as Sonny, an irresponsible slacker, is forced to take on the biggest responsibility of them all: caring for a child. He doesn’t have a clue what he’s doing, but soon, the two warm up to one another and share a beautiful bond. That isn’t without tons of hijinks leading up to that point, though, as Sonny teaches Julian everything a five-year-old shouldn’t learn, but in the funniest ways possible.

Big Daddy

Release Date

June 25, 1999

Cast

Adam Sandler , Joey Lauren Adams , Jon Stewart , Cole Sprouse , Dylan Sprouse , Josh Mostel

Runtime

93

Main Genre

Comedy

Writers

Steve Franks , Tim Herlihy , Adam Sandler

Director

Dennis Dugan

Big Daddy can be streamed on Starz in the U.S.

Watch on Starz

2 ‘Billy Madison’ (1995)

Directed by Tamra Davis

In Billy Madison, Sandler is the title character, sone of a wealthy tycoon who has wasted his life drinking and causing trouble with his friends. When he learns that his father doesn’t think he is fit to run the company once, he retires and is instead going to hand it over to his villainous vice president, Billy panics. Learning that his father paid off his teachers all through school to pass him, he vows to complete every grade to prove to his father that he’s worthy. A grown man reliving kindergarten, middle school, and high school is naturally hilarious, as are Billy’s reactions and interactions with kids who have now become his much smaller but not so much more immature peers.

Arguably the movie that put Sandler on the map and the first in which he starred through his own production company after being fired from Saturday Night Live (SNL), Billy Madison is one of those movies filled with funny one-liners. From his conversation with shampoo and conditioner bottles to his objection to the storyline during kindergarten storytime, the movie is filled with laughs the entire way through. It’s one of many Sandler movies that critics hated but audiences love, and continue to love to this day.

Billy Madison can be streamed on Starz in the U.S.

Watch on Starz

1 Happy Gilmore (1996)

Directed by Dennis Dugan

A sports comedy and yet another hit for Sandler in the ‘90s, Happy Gilmore is about a failed hockey player who apparently has a knack for golf. With the help of former professional golf pro Chubbs Peterson (Carl Weathers), Happy tries to make it all the way to the top. He needed to win the prize money for his grandmother who is about to be evicted from her home. But it isn’t going to be easy, especially with the arrogant Shooter McGavin (Christopher McDonald) aiming for the win and looking to find every way to antagonize Happy.

That’s not difficult since Happy has that hockey mentality, ready for a fight at every moment, the complete antithesis of golf. He brings that aggressive attitude onto the green in the most hilarious way, throwing golf clubs, screaming at balls, and even getting into a fist fight with Bob Barker (who plays himself in the memorable scene). Like other Sandler movies, there are the themes of a hero, a villain, and the underdog. It’s his usual schtick, but that’s precisely what fans love about the movie.

Happy Gilmore can be streamed on Starz in the U.S.

Watch on Starz

KEEP READING: Every Adam Sandler Netflix Movie, Ranked