Like 'Happy Gilmore 2?' Here's the 10 best Adam Sandler movies on Netflix, Prime Video and more

Tom's Guide

5 days ago

Adam Sandler is easily one of the biggest comedy stars in Hollywood, and the success of Netflix's newest original, "Happy Gilmore 2," shows audiences still can't get enough. Though critics have taken shots at him for decades, Sandler has built a devoted fanbase thanks to his relatable everyman charm and comedic chops.
If "Happy Gilmore 2" has you eager to rewatch some of Sandler's greatest hits, we've got you covered. Several of Sandler's most iconic comedies like "The Water Boy" and "Punch-Drunk Love" are only available to rent or buy, but there are still plenty to find across the best streaming services — including some you can watch for free.
So without further ado, let's dive into where you can watch all the best Adam Sandler comedies on Prime Video, Netflix, and more.
"Billy Madison" is one of Sandler's earliest starring roles, and it ranks alongside "Happy Madison" as one of the comedian's most beloved earlier entries. He plays Billy, a pampered young heir to a massive hotel chain and the gold standard in man-child comedy. After wrecking an important dinner with his usual antics, his father, Brian Madison (Darren McGavin), decides to leave his empire to someone more responsible when he retires.
Determined to prove himself, Billy convinces his father to give him one last chance with an absurd challenge: to return to school and pass all 12 grades. "Billy Madison" was another early entry that cemented Sandler's legacy of iconic characters and endlessly quotable one-liners. It's all a bit ridiculous, but given the wild premise, that's exactly what makes it so charming.
"Big Daddy" is the perfect example of a movie that fell flat with critics but is still a favorite for Sandler fans. The 1999 comedy classic stars Sandler as Sonny Koufax, an unemployed law school grad coasting off a settlement from an accident payout.
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To prove to his ex-girlfriend that he's ready to grow up, he 'adopts' a 5-year-old boy named Julian (played by twins Cole and Dylan Sprouse). Together, they get up to all kinds of mischief around Manhattan, but important life lessons manage to peek through all the mayhem.
"Big Daddy" is Sandler in peak dad mode, and in retrospect, it feels like a midway point between his silly man-child roles and his more experimental and rom-com era to come.
With blockbusters like "The Waterboy" and "Big Daddy" under his belt, Sandler unleashed one of his most bizarre films to date with "Little Nicky, a unique blend of dark fantasy with frat-boy humor. Sandler stars as the titular son of Satan (Harvey Keitel) and a radiant angel (Reese Witherspoon).
When his two brothers scheme to claim the throne of the underworld by unleashing chaos on Earth, Nicky sets out to stop them. But that's a tall order for a hopelessly inept, emo-haired oddball with a speech impediment.
"Little Nicky" was a critical and commercial flop that stalled Sandler's career momentum in his prime, but in the decades since, it's developed a cult following, largely thanks to Sandler's unhinged performance.
With "Mr. Deeds," Sandler and his longtime collaborators, writer Tim Herlihy and director Stephen Brill, take on a remake of a Hollywood classic: the 1930s Frank Capra- and Gary Cooper-led film "Mr. Deeds Goes To Town." Some details have obviously changed, but "Mr. Deeds" keeps the general story intact.
Lovable small-town pizza guy Longfellow Deeds (Sandler) gets the shock of a lifetime when he unexpectedly inherits his uncle's vast estate, including a grand mansion and media empire. As insiders within the company scheme to take him down, ambitious reporter Babe Bennett (Winona Ryder) sets out to get close to Deeds, hoping to land an exclusive story, but ends up getting more than she bargained for when sparks start to fly.
When Sandler teamed up with screen legend Jack Nicholson for "Anger Management," it marked a turning point in his career. Sandler plays the mild-mannered Dave Buznik, who's sentenced to anger management after a misunderstanding on a flight spirals out of control.
His life is turned upside-down when he's assigned to the unconventional (and increasingly invasive) therapist Buddy Rydell (Jack Nicholson), who moves in with him to provide hands-on treatment for his supposed anger issues. It's rare we see Sandler play the straight man for a change, and "Anger Management" stands out for Nicholson's larger-than-life performance and the surprisingly strong comedic chemistry the two share.
Watch 'Anger Management' now on Tubi
Considering the undeniable chemistry they had in "The Wedding Singer," it's a wonder it took Sandler and Drew Barrymore six years to reunite for another romantic comedy. But it was worth the wait for "50 First Dates." Sandler plays Henry Roth, a commitment-phobic marine veterinarian living in Hawaii.
He meets his match with Barrymore's Lucy, a kind-hearted art teacher who suffers from short-term memory loss after a car accident. Every day, she wakes up thinking it's the same day, leaving Henry to win her over again and again, one meet-cute at a time. It's a quirky but sweet rom-com with all the classic Sandler touches you'd expect: a signature Sandler guitar song, Rob Schneider in a wildly over-the-top supporting role, and a scene-stealing walrus named Jocko.
Watch '50 First Dates' now on Netflix
Stepping into the cleats of Burt Reynolds, Sandler takes a surprisingly faithful approach to this remake of the 1974 classic "The Longest Yard." As Paul Crewe, a disgraced former NFL quarterback who lands behind bars after violating probation, Sandler blends humor with just enough heart to make the role his own while preserving the original's gritty yet entertaining tone.
To entertain a warden, Paul attempts to lead a team of inmates onto the gridiron. But before he can put a squad together, he'll first have to earn the respect of his fellow prisoners. While it may not hit the same legendary status as the original, Sandler's version still scores — maybe not a touchdown, but a solid two-point conversion.
Watch 'The Longest Yard' now on Hulu
"Happy Gilmore" director Dennis Dugan and Sandler team up once more in "You Don't Mess with the Zohan," a wildly absurd comedy centered around an Israeli counterterrorism commando whose true passion is hairstyling rather than espionage.
With an over-the-top love for hummus, an exaggerated wardrobe full of unbuttoned shirts, and a cartoonishly large bulge, Sandler tries to bring levity to a thorny subject. Like "Happy Gilmore," the film is also packed with unexpected cameos, from Chris Rock and Henry Winkler to Mariah Carey and, most bizarrely, Dave Matthews playing a clueless white supremacist. It all adds to the film's chaotic charm.
Watch 'You Don't Mess with the Zohan' now on Hulu
If you liked Sandler's more dramatic turn in "Uncut Gems" but are still looking for something with a healthy helping of laughs, "Hustle" deserves a spot on your watchlist. Sandler delivers a standout performance as Stanley Sugarman, a down-on-his-luck basketball scout for the Philadelphia 76ers who discovers an unpolished but gifted player, Bo Cruz (Juancho Hernangómez), while overseas.
Stanley brings him to the U.S. with hopes that Bo will be picked up by the 76ers or another NBA team — and reboot his own career in the process. NBA fans will especially enjoy the many cameos from real players, past and present, but the film's emotional core and Sandler's performance make it resonate with audiences well beyond the sports world.
Watch 'Hustle' now on Netflix
It's nearly impossible to talk about Sandler's best movies without shouting out his standout romantic comedy "The Wedding Singer." Sandler stars as Robbie Hart, the eponymous singer who's left broken-hearted after his fiancée dumps him at the altar.
Robbie's life takes a turn when he meets Julia Sullivan (Drew Barrymore), a waitress working many of the same gigs. As fate would have it, Julia is also engaged, setting the stage for a romantic dilemma.
Uncharacteristically sweet for a '90s Sandler film, "The Wedding Singer" marked his first of many collaborations with Barrymore. While the plot hits a lot of familiar tropes, it's the winning combination of comedy and chemistry between Sandler and Barrymore that makes this film shine.
Watch 'The Wedding Singer' now on Tubi
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