Adam Sandler's best movies

By Jillian Schenfeld 6:34am PST, Feb 17, 2021

It's been 25 years since "Happy Gilmore" first opened in theaters on Feb. 16, 1996. In the cult comedy, Adam Sandler stars as a hapless hockey player who discovers that he might actually have a talent for playing an entirely different sport: golf. In honor of its big anniversary, Wonderwall.com is taking a look back at more of the funnyman's best movies from over the years. Keep reading to see if your favorite made the list…

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In 2020's "Uncut Gems," Adam Sandler stars as Howard Ratner, a jeweler based in New York City's Diamond District who has a serious gambling addiction. The film chronicles Howard's experiences as he attempts to appease his family and clients while risking everything in a high-stakes bet. The National Board of Review listed the film as one of the top 10 films of 2019. It also banked $50 million at the box office, setting a record as distributor A24's highest grossing domestic film. Critics largely agreed "Uncut Gems" was some of Adam's best work to date — he even won a Film Independent Spirit Award for best actor.

Another one of Adam Sandler's best, 1998's "The Wedding Singer," is a testament to the incredible chemistry between the funnyman and Drew Barrymore. The film takes places in the '80s and follows Robbie Hart, a wedding singer from New Jersey who falls in love with waitress Julia Sullivan (Drew). The kicker: Julia is engaged to unfaithful jock Glenn. But all's fair in love and war in this predictable yet well-done film, which earned a 69% fresh rating with critics on Rotten Tomatoes.

Time for another fantastic Adam Sandler–Drew Barrymore collaboration… In 2004's "50 First Dates," Adam stars as Henry Roth, a womanizing veterinarian who falls in love with Drew's character, Lucy, a lovely woman suffering from short-term memory loss. The movie received mixed reviews from critics, but fans were charmed by the undeniable chemistry between the two leads.

Rounding out the Adam Sandler–Drew Barrymore trifecta is 2014's "Blended." The family comedy follows a recent divorcée and a widowed father who, after going on a terrible blind date with one another, find themselves sharing the same vacation package while at a South African resort. As a result, these two strangers, who assumed they'd never have to see each other again, are forced to go on a a series of family excursions with their respective children. Critics may not have been impressed, but the film still earned $128 million on a $40 million budget. Truthfully, Drew and Adam's chemistry is reason enough to give it a watch!

In "Big Daddy," Adam Sandler stars as lazy law school graduate Sonny Koufax, who finds purpose when he's tasked with suddenly caring for a ridiculously cute 5-year-old boy, Julian. (Dylan Sprouse and Cole Sprouse shared the role, which marked their feature film debut.) The dramedy — which also stars Leslie Mann, Jon Stewart, Joey Lauren Adams and Steve Buscemi — is both heartfelt and hilarious, zeroing in on that emotional-yet-funny sweet spot. The film won a People's Choice Award for favorite comedy in 2000, though the late film critic Roger Ebert ragged on it for having a "predictable story arc."

Iconic! Adam Sandler stars as Bobby Boucher — the titular water boy for the struggling University of Louisiana football program — in the 1998 sports comedy "The Waterboy," which critics loathed but audiences loved. Despite its dismal 34% fresh rating with critics on Rotten Tomatoes, the insanely quotable film — which features a hilarious turn by Oscar winner Kathy Bates as Bobby's Mama — banked $190 million on a $23 million budget.

Though it failed to make an impression at the box office, critics loved the 2002 Paul Thomas Anderson romantic dramedy "Punch-Drunk Love." Adam Sandler actually earned his first and only Golden Globe nomination for his performance as Barry Egan, a socially awkward small-business owner with seven manipulative sisters who, after some trials and tribulations, eventually finds love with Emily Watson's character, Lena.

In "Billy Madison," Adam Sandler stars as the titular spoiled man-child and heir to a Fortune 500 company who's challenged by his father to go back to school to prove that he can take over the family business. Billy sings in the 1995 comedy, "Back to school, back to school, to prove to Dad that I'm not a fool." He also ends up falling in love with a pretty teacher and eventually proves himself to be a sort-of responsible guy with a better outlook on life. One critic warned, "As one might suspect, 'Billy Madison' is not for every taste; Sandler fans will laugh from start to finish; others beware." Billy Mowbray of "Film4" gave the flick a positive review, writing: "When you get that Sandler's comedic persona is meant to be annoying, like Beavis and Butthead or Cartman, the laughs come thick and fast." In other words, if you love Adam, it's a given you'll love "Billy Madison."

Adam Sandler plus Jennifer Aniston equals comedy gold! Based on the 1969 film "Cactus Flower," 2011's "Just Go With It" stars Adam as Danny Maccabee, a successful plastic surgeon who convinces his assistant, Katherine Murphy (Jen), to pretend to be his wife, from whom he's almost divorced, in an effort to capture the affection of a young teacher (Brooklyn Decker). Of course, as time progresses and their lie deepens, so do their real feelings for one another. While the film feels like your prototypical rom-com, it's elevated by the chemistry between the leads. The comedy was also considered a major box office success — it earned $215 million on a $48 million budget!

Adam Sandler and Jennifer Aniston reunited for the 2019 Netflix comedy "Murder Mystery." They starred as Nick and Audrey, a New York police officer and his hairdresser wife who accidentally get caught up in a homicide investigation on a billionaire's yacht while vacationing in Europe for their 15th anniversary. Critics didn't love it, but fans did: It won the favorite comedic movie prize at the 2019 People's Choice Awards.

In 2003's "Anger Management," Adam Sandler stars as Dave Buznik, a generally mild-mannered man who, after an unsettling incident on an airplane, is forced to attend anger management classes to avoid jail time. There, he meets Dr. Buddy Rydell (Jack Nicholson), an unconventional therapist who decides to move in with him in an effort to correct his behavior. The film, which earned $195.7 million on a $83.5 million budget, was also turned into a television series — the "Anger Management" TV show premiered in 2012 and starred Charlie Sheen as Dr. Charlie Goodson (a version of Jack's role). The series ran for two seasons until 2014.

Adam Sandler teamed up with fellow funnymen Kevin James, Chris Rock, David Spade and Rob Schneider — as well as A-list actresses Salma Hayek, Maria Bello and Maya Rudolph — for the 2010 ensemble comedy "Grown Ups," which centers around five best friends who reunite 30 years after their junior high school basketball championship to celebrate the life of their late beloved coach. In spite of dismal reviews (it scored an 11% fresh rating from critics on Rotten Tomatoes), the film earned a whopping $271.4 million on an $80 million budget and spawned a 2013 sequel.

Judd Apatow wrote and directed the 2009 dark comedy "Funny People," which sees Adam Sandler playing a retired stand-up comedian and movie star who attempts to patch up some of his strained relationships when he's diagnosed with potentially fatal leukemia. This emotional yet funny film features a star-studded supporting cast including Seth Rogen, Leslie Mann, Aubrey Plaza, Aziz Ansari and more. While it performed decently with critics, audiences mostly failed to turn up to catch it in theaters. Fortunately, "Funny People" has developed more of a fan following since then.

The 2017 film "The Meyerowitz Stories," which was written and directed by Noah Baumbach, chronicles an estranged group of siblings who reunite in New York City in celebration of their father's artistic career. Adam Sandler stars as Danny Meyerowitz, the unemployed, musically talented and recently separated son of Harold (Dustin Hoffman). Adam received widespread acclaim from critics for his work in the film, with Variety's Peter Debruge writing, "With no shtick to fall back on, Sandler is forced to act, and it's a glorious thing to watch — even for those fans who like him best in perpetual man-child mode (don't worry: the character is a full-grown variation on that familiar Sandler prototype)."

Nearly a decade after "The Waterboy," Adam Sandler returned to football in the 2005 remake of "The Longest Yard." (Burt Reynolds headlined the original.) He stars as disgraced former NFL quarterback Paul Crewe who, while serving time behind bars, ends up overseeing the inmates' football team as they gear up for a game against a team comprised of prison guards who will stop at nothing to cheat their way to victory. In spite of dismal reviews, the sports comedy performed well at the box office, banking $190.3 million on an $82 million budget.

In 2004's "Spanglish" — one of Adam Sandler's earliest dramatic roles — the comedian stars as a chef who forms a connection with his family's Spanish-speaking housekeeper (Paz Vega) while navigating his increasingly broken marriage with his emotionally abusive and adulterous wife (Téa Leoni). Although the funnyman earned raves for his dramatic turn, the romantic dramedy ultimately received mixed reviews from critics.

Not everyone's a fan of "Little Nicky" humor — which is why it generally flopped with critics and at the box office — but the 2000 comedy has developed a strong cult following over the years. Adam Sandler stars as Satan's kind son Nicky, who's tasked with stopping his two evil brothers from creating Hell on Earth. If a lazy Sunday presents itself and you have a few hours to spare, you'll likely have some laughs with this flick, which features future Oscar winners Reese Witherspoon (as Nicky's Angel mom) and Patricia Arquette (as his love interest).

In 2006's "Click," Adam Sandler stars as Michael, an overworked architect who acquires a universal remote that enables him to fast-forward through the less enjoyable parts of life, which ultimately ends up teaching him a bigger life lesson. Kate Beckinsale plays Donna, his wife. Roger Ebert gave the film 2 of out 4 stars for misrepresenting itself as a comedy when it's really pretty melancholy. It's definitely not your typical Sandler film!

"Reign Over Me" is a lesser-known Adam Sandler film also starring Don Cheadle, Jada Pinkett Smith, Liv Tyler and Donald Sutherland. The 2007 drama centers around Adam's character, Charlie, who reconnects with a college pal played by Don after losing his wife and daughters in the 9/11 attack on the World Trade Center. The film received a 64% fresh rating from critics on Rotten Tomatoes but scored significantly higher than that with audiences.