Adam Sandler has been a Hollywood fixture since he broke out on Saturday Night Live in the early 90s. He dominated the box office as one of its most bankable comedy stars, and his movies, while not garnering much critical attention, have become oft-quoted fan favorites.

In the new millennium, Sandler’s career has seen its fair share of ups and downs, with some of the star’s comedies being called the worst of their decade, but he also expanded the range of roles he took on and worked with some of the best directors of their generation. With a lucrative deal at Netflix and multiple projects in the pipeline, the Sandman doesn’t show any signs of slowing down, so it’s a good time to take a look back at the most essential movies of his career.

10

‘The Waterboy’ (1998)

Directed by Frank Coraci

Sandler was one of the most reliable hit-makers of comedies through the latter half of the 90s into the 00s. While most of them never garnered much critical acclaim they were big hits with audiences. The formula for many of these involved Sandler as a character (sometimes with a funny voice, sometimes not) stuck in a state of arrested development; man-children. The apex of this character is Bobby Boucher, the H2O-loving mama’s boy in the college football comedy The Waterboy.

Sandler’s second collaboration with director Frank Coraci, The Waterboy leans into physical comedy and Sandler’s penchant for broad character work. On that scale, the movie is leagues ahead of Sandler’s similar work in movies like Little Nicky or Hubie Halloween. As Boucher, Sandler is the ultimate underdog, a simple man with an overprotective mother who finds he has a gift for football when he unleashes his years of pent-up rage. Add to that hilarious supporting turns from Kathy Bates and Henry Winkler, and the result is a goofy comedy with just enough heart.

The Waterboy

Release Date

November 6, 1998

Runtime

90 Minutes

Director

Frank Coraci

9

‘Hotel Transylvania’ (2012)

Directed by Genndy Tartakovsky

Sandler hasn’t limited his wacky antics to the live-action medium and while his first animated film, the Hanukkah comedy Eight Crazy Nights, should be erased from memory, his second turn in the medium led to a family-friendly Halloween franchise. Hotel Transylvania was the first feature film for acclaimed director Genndy Tartakovsky, an animation legend thanks to his work on series such as The Powerpuff Girls, Dexter’s Laboratory, and Samurai Jack.

Tartakovsky’s signature fast-paced style was a perfect match for Sandler’s over-the-top delivery as Dracula, who here has become a dorky dad who runs a hotel exclusive to monsters. The visual gags come fast and furious and the other classic monster characters are voiced by several Sandler associates, such as Kevin James as Frankenstein. Sandler is well suited to playing the madcap Drac, and he even surprisingly brings some pathos to the character’s tragic backstory.

Hotel Transylvania

Release Date

September 28, 2012

Runtime

91 minutes

Director

Genndy Tartakovsky

8

‘Billy Madison’ (1995)

Directed by Tamra Davis

Sandler’s first major leading role (unless one includes Going Overboard, which they shouldn’t), Billy Madison is the star’s childish comedic persona at its most surreal. The concept of the movie is so patently ridiculous it’s brilliant. Sandler plays the titular character, who is a spoiled rich kid who must retake all his primary and secondary education classes in order to inherit his family fortune.

The absurdist plot is just an excuse to unleash Sandler in a variety of school settings, and that’s enough to sustain the entire runtime. The worst of Sandler’s high-concept comedies feel like poorly written sketches stretched out to feature length, but Billy Madison manages to keep surprising its audience with its bizarre plot turns and non sequitur gags, so that it stays fresh and always funny.

Billy Madison

Release Date

February 10, 1995

Runtime

89 minutes

Director

Tamra Davis

7

‘Funny People’ (2009)

Directed by Judd Apatow

Sandler has never put much stock in what critics think of his work. He enjoys making movies with his friends and has fun doing it. There’s really no faulting that. Only once has Sandler ever shown any real self-reflection in his career, in Judd Apatow’s Funny People. Sandler plays a crooked version of himself (sans wife and kids), a once beloved comedian who has since become better known for his bad high-concept movies, and who then gets a life-altering medical diagnosis.

Apatow teams Sandler up with Seth Rogen as an aspiring comedian who he takes under his wing. Not all of the movie works. Apatow’s direction had become a little too overindulgent at this point and the movie meanders for far too long, but there is still a lot of incisive humor regarding Sandler’s career and the entertainment industry at large. The greatest joke of all is how immediately Sandler returned to the juvenile kinds of comedy this film was largely deriding, proving the actor is always the one to have the last laugh.

Funny People

Release Date

July 22, 2009

Runtime

146minutes

Director

Judd Apatow

6

‘Hustle’ (2022)

Directed by Jeremiah Zeger

Sports have been a major part of Sandler’s movie career. His most recent sports film, Hustle, stands out from the rest by simple virtue of the fact that it isn’t a zany comedy. It’s also just really good. Sandler plays an NBA talent scout whose career has taken a personal toll, but when he discovers an untapped talent in a Spanish basketball player (played by real-life sports star Juancho Hernangómez), he gets a new lease on life and his career.

It’s the kind of underdog sports story that easily wins over audiences, but Sandler’s understated performance and natural charm help it rise above sports movie clichés. Hustle is one of the best Sandler movies to come out of the actor’s long-term deal with Netflix and ranks well among the actor’s more dramatic performances.

Hustle

Release Date

June 8, 2022

5

‘Happy Gilmore’ (1996)

Directed by Dennis Dugan

Blah blah blah surprising dramatic performance blah blah. What audiences really love is when Adam Sandler is funny, and he’s never been funnier than in Happy Gilmore. As an aggressive hockey player who turns to golf to save his grandmother’s home, Sandler’s unique comic timing and sensibilities have never been better utilized. Also, him getting punched by Bob Barker is comedy gold. No further explanation needed.

The film’s laugh meter is also boosted by terrific supporting performers. Carl Weathers plays on his sports movie icon status as Sandler’s golf pro mentor, and comedy pros Ben Stiller and Joe Flaherty both have hysterically funny small roles. The MVP, though, goes to Christopher McDonald as Shooter McGavin, one of the best comedic villains ever, and who has a questionable breakfast diet. It’s unlikely the upcoming Netflix sequel will be able to recapture the comedic glory of this original, but Sandler’s trophy for this comedy classic isn’t going anywhere.

Happy Gilmore

Release Date

February 16, 1996

Runtime

92 minutes

Director

Dennis Dugan

4

‘The Meyerowitz Stories (New and Selected)’ (2017)

Directed by Noah Baumbach

Sandler’s most underrated performance came in this dramedy about a dysfunctional New York family. The Meyerowitz Stories focuses on a family led by Dustin Hoffman as a retired art professor. Sandler is the eldest brother at a crossroads in life after a divorce, and Ben Stiller is his more successful sibling. Sandler and Stiller compete for their father’s approval and the two comedic actors have a wonderfully contentious chemistry together, along with Hoffman, who buries his character’s own insecurities under criticism.

Sandler has shown on multiple occasions his ability to perform above and beyond the broad characters he became famous for. Reign Over Me is an uneven film focusing on post-9/11 grief that is elevated by Sandler’s performance, and Spaceman’s outlandish concept is grounded by the actor’s naturalism. Baumbach is able to harness some of Sandler’s biggest strengths (comedic rage and musical proclivity) in service of a down-to-earth character. The two seem to have enjoyed the collaboration as they will be re-teaming for another Netflix joint with George Clooney.

The Meyerowitz Stories (New and Selected)

Release Date

October 13, 2017

Runtime

112 minutes

Director

Noah Baumbach

3

‘The Wedding Singer’ (1998)

Directed by Frank Coraci

Back when romantic comedies were still regularly released in theaters, Sandler was one of the highest grossing stars of the genre, and his best collaborator was Drew Barrymore. Even if the film wasn’t very good, the two stars brought out the best in each other. Their best film together was the career shifting The Wedding Singer.

Featuring Sandler in the title role as a wedding singer who is heartbroken after being left at the altar, he finds a new love with Barrymore’s waitress Julia, who is herself engaged to be married. The movie is still filled with much of the goofy humor that was indicative of Sandler’s career at the time, but it also allowed the actor to flex his dramatic muscles far more than he had ever been asked to before. The Wedding Singer was utilizing Sandler’s subtle range years before any arthouse directors picked up on it, and it did it while still having a rapping granny.

The Wedding Singer

Release Date

February 13, 1998

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2

‘Punch-Drunk Love’ (2002)

Directed by Paul Thomas Anderson

The pairing of Sandler and director Paul Thomas Anderson, known then for Boogie Nights and Magnolia, certainly turned a few heads, and even today the film is a bit of an outlier in the director’s filmography. The two proved to be a perfect match for Punch-Drunk Love, a melancholy rom-com that transcends the genre’s clichés. Sandler plays Barry, a socially isolated man prone to fits of rage. He meets Emily Watson’s Lena and the two embark on a romance that’s filled with bizarre interludes, including a memorable appearance by Philip Seymour Hoffman.

While the arthouse rom-com wasn’t a financial success, it’s legacy endures thanks to its strong reputation among other filmmakers. It also served as a compelling argument for Sandler as an actor of significantly more depth than previously thought, and he stated during a retrospective that the film directly contributed to the expansion of his career outside broad comedies.

Punch-Drunk Love

Release Date

November 1, 2002

Runtime

95 minutes

Director

Paul Thomas Anderson

1

‘Uncut Gems’ (2019)

Directed by Josh and Benny Safdie

Comedic actors exploring their dark side never seems to lose its novelty. Audiences loved it when Robin Williams did it in One Hour Photo or Steve Carell in Foxcatcher, and they absolutely went wild for Sandler in the Safdie Brothers gambling thriller Uncut Gems. It’s a movie that throws the audience off balance early and keeps them there for over two hours. Sandler plays Howard, a jeweler in New York’s Diamond District who also has a terrible gambling addiction, with a wound up tension never before displayed by the actor.

The Safdie’s ratchet up the anxiety in the same way as in their heist thriller Good Time and Sandler is pitch perfect throughout, always keeping the audience on edge, hoping and praying the character will make the right choice before his addiction gets the best of him. It’s a completely committed performance that, of course, was overlooked by major Awards groups but proves that Sandler is still one of the most consistently undervalued actors.