The Best Adam Sandler Movies of All Time

Image via Universal Pictures

Director: Frank Coarci

Starring: Adam Sandler, Kate Beckinsale, Christopher Walken

Adam Sandler’s film output in the 2000s is mixed to say the least. The releases of Little Nicky, Mr. Deeds, and Eight Crazy Nights at the turn of the millenium left Sandler critically lambasted and audiences largely indifferent. It wasn’t until 2006’s Click that Sandler would find himself back in the good graces of movie audiences. Click stars Sandler as Michael Newman, an architect that neglects his family who acquires a “universal remote” from stranger Morty (Christopher Walken), that allows him fast forward through boring or hard parts of his life. By this point, Adam Sandler’s career had seen him dabble with dramatic performances like Punch-Drunk Love and Spanglish. Click finds the perfect balance between the two tones of his career, with plenty of gross out humor (including a scene where Sandler farts in the face of his boss—played by David Hasselhoff—while he’s “paused”) but also plenty of bittersweet, emotional drama when Michael discovers all that he’s lost from fast-forwarding through life with his family. While definitely on the lower end of Sandler’s output, Click is fun and surprisingly emotional.

Director: Judd Apatow

Starring: Adam Sandler, Leslie Mann, Seth Rogen

In the late aughts, Judd Apatow was the comedy king of Hollywood. He had directed two huge hits (The 40 Year Old Virgin and Knocked Up) and produced countless other successful comedy films, leaving his distinctive stamp on the business of comedy. His much anticipated follow-up to Knocked Up finally came in 2009 with Funny People. It follows comedian George Simmons (Sandler) as he’s diagnosed with terminal cancer and tries to fix his relationships with those closest to him, including aspiring standup comedian Ira (Seth Rogen) and ex-fiance Laura (Leslie Mann). Funny People does have some problems: at 146 minutes it’s awfully long and the comedy-to-drama ratio can feel a bit off for most of its runtime, but the thing that’s solid about it is Sandler himself. Funny People feels autobiographical for both Sandler and Apatow, as two older comedians reconciling with the toll being in show business takes on their personal and professional lives. While not among Judd Apatow’s best, Funny People is a solid showcase for Serious Sandler.

Director: Tamra Davis 

Starring: Adam Sandler, Bradley Whitford, Bridgette Wilson

The film that put Adam Sandler’s career on the map, Billy Madison is a beloved ‘90s comedy classic. The film follows the titular hotel heir (Sandler) as he repeats the first through twelfth grades in two weeks to prove to his father (Darren McGavin) that he is worthy of inheriting his empire. Billy Madison gave birth to the Adam Sandler persona as we know it today: Billy is immature, ridiculous, and frequently participates in gross out humor, much to the chagrin of the many adults around him. Sandler quickly became a comedy hero to many young filmgoers with this movie, and despite mixed critical reviews, Billy Madison was a financial success and created the very idea of the “Adam Sandler comedy”.

Director: Dennis Dugan

Starring: Adam Sandler, Joey Lauren Adams, Cole & Dylan Sprouse

Way before he could ever dream of playing Jughead on Riverdale, Cole Sprouse was acting opposite Adam Sandler in one of his most beloved movies. Big Daddy follows slacker Sonny (Sandler) as he finds himself raising a child (Cole and Dylan Sprouse) in order to impress his girlfriend, but soon finds himself the child’s unlikely foster father. Sandler’s last film before the creation of his own production company Happy Madison Productions, Big Daddy is the film that continued to cement Sandler’s movie star career, and his persona as a lovable loser. Numerous kids who were too young to watch the movie can quote it all too well (“Somebody get this kid a Happy Meal!” is a classic). It’s not the deepest or smartest of his comedies, but Big Daddy boasts strong comedic chemistry between the Sprouses and Sandler, as well as a fun and entertaining story. 

Director: Kyle Newacheck

Starring: Adam Sandler, Jennifer Aniston, Luke Evans

Adam Sandler’s film production deal with Neflix has yielded some lows and… mostly lows (films like The Do-Over and The Week Of are mostly forgettable but The Ridiculous Six is truly horrific), but Murder Mystery has proved itself to be a surprisingly delightful result of the collaboration. The movie follows married couple Nick (Sandler) and Audrey (Jennifer Aniston) as they’re invited onto the yacht of billionaire Charles Cavendish (Luke Evans) and find themselves embroiled in a real life murder mystery when Cavendish’s uncle is found dead. Refreshingly high concept, Murder Mystery leans into its genre trappings and has a lot of fun with its self aware whodunnit plot. The film also boasts a better cast than usual Sandler productions, with Terence Stamp and Gemma Arterton in prominent roles. Inspired and reliably entertaining, Murder Mystery is one of the few recent Adam Sandler movies that recaptures some of his comedic glory days. 

Director: Dennis Dugan

Starring: Adam Sandler, Christopher McDonald, Julie Bowen

The second collaboration between Adam Sandler and frequent writing partner Tim Herlihy after Billy Madison, Happy Gilmore is very much in the vein of Billy Madison, further playing into the Adam Sandler persona. The movie centers on Happy Gilmore (Sandler), an aspiring hockey player, who discovers an affinity for golf and enters the PGA Tour in order to save his grandmother’s house, drawing the ire of pro golf player Scooter McGavin (Christopher McDonald). Billy Madison was already pretty over the top, but Happy Gilmore goes to even more surreal humor with Adam Sandler fighting Bob Barker, who plays himself (“The price is right, bitch!”). Happy Gilmore won’t turn any hardcore Adam Sandler haters into fans, but it’s Sandler doing what he does best with likable characters and an inspired sense of lunacy. 

Director: Michael Lehmann

Starring: Brendan Fraser, Steve Buscemi, Adam Sandler

Before even Billy Madison, Adam Sandler was still turning in solid supporting roles in comedies. Catapulting from his popular turn on Saturday Night Live, he landed supporting roles in Coneheads and Airheads, the latter of which is his one of his most underrated roles. Airheads follows heavy metal rock band members Chazz (Brendan Fraser), Rex (Steve Buscemi) and Pip (Adam Sandler) as they hijack a radio station and take the DJs hostage until they agree to air their demo tape. You’re reading that correctly: Adam Sandler once starred in a heavy metal comedy with Brendan Fraser and Steve Buscemi, and it’s pretty fun. Not a smart comedy by any means, what Airheads makes up for in lack of intelligence is its broad 90’s comedy humor, bolstered by comedic heavy hitters such as Chris Farley, Michael McKean, and David Arquette in supporting roles. Airheads finds Adam Sandler playing second fiddle to a ridiculously stacked cast and he holds his own remarkably well.

Director: Frank Coraci 

Starring: Adam Sandler, Drew Barrymore, Christine Taylor

While not entirely dramatic, The Wedding Singer finds Adam Sandler acting slightly more mature than he does in his most famous roles. The movie centers on Robbie (Sandler), a rock star turned wedding singer, as he’s dumped on the day of his wedding and finds himself falling for waitress Julia (Drew Barrymore), who just set her wedding date with her own fiancee. In a stark difference from many of Sandler’s earlier movies, The Wedding Singer is almost too earnest and doesn’t have much of the same humor of Billy Madison and Happy Gilmore. The movie is an out and out romantic comedy that hits all of the beats you expect it to, and proudly. The Wedding Singer was the first evidence that Sandler had range and could use our idea of the types of characters he usually plays to surprise us.

Director: Noah Baumbach

Starring: Adam Sandler, Ben Stiller, Dustin Hoffman

Director Noah Baumbach’s career has been filled with caustic tales of people who can’t help but fight with their friends and family. The Meyerowitz Stories (New and Selected) is definitely a piece of his oeuvre, but boasts some surprising heavy hitters in the cast, including Dustin Hoffman and, of course, Adam Sandler. The movie follows a group of dysfunctional New York adult siblings (Elizabeth Marvel, Ben Stiller, Sandler) as they try to live in the shadow of their difficult father (Hoffman). While the themes explored aren’t anything new for fans of Baumbach, The Meyerowitz Stories turns surprisingly tender despite its outwardly prickly dialogue. Sandler in particular gives one of the most nuanced performances of his career as a separated dad trying desperately to understand both his father and his daughter. The Meyerowitz Stories (New and Selected) is a career high point for Sandler. 

Director: Paul Thomas Anderson

Starring: Adam Sandler, Emily Watson, Philip Seymour Hoffman

Paul Thomas Anderson’s Magnolia was released in 1999 to mixed reviews: at almost three hours it was overlong, it was a bit melodramatic, and it was nothing like his previous movie, 1997’s crowd pleasing Boogie Nights. In response to the tepid critical reaction, Anderson did a complete 180 for his next film: a 90-minute romantic comedy starring, of all people, Adam Sandler. To this day, Punch Drunk Love remains one of Anderson’s best movies and Adam Sandler’s best movie to date. The movie centers on Barry Egan (Adam Sandler), a maladjusted novelty supplier, as he falls in love with his sister’s friend Lena (Emily Watson) and is extorted by a crooked mattress salesman (Philip Seymour Hoffman). What’s most fascinating about Punch Drunk Love is that it often feels like an arthouse version of the typical Adam Sandler comedy. There’s the beautiful love interest, the childish main character who’s nowhere near as attractive, and a ludicrous, almost nonsensical plot to add action to the proceedings. Punch Drunk Love adds emotion, great performances, visceral direction, and a hint of expressionism to this formula, making Barry seem all too real even when he’s acting larger than life. His greatest and most left field role ever (at the time and even now), Punch Drunk Love is Adam Sandler at his very best and most surprising.