It’s impossible to talk about ‘90s comedy without bringing upAdam Sandlerand his loud, over-the-top, lovable presence, where he is probably yelling, singing off-key, speaking in silly voices, or starting a bar fight with a golf ball. Emerging from the chaos ofSaturday Night Live’sgolden era, Sandler brought with him a brand of humor that combined absurdity, juvenile mischief, and subtle sweetness. Whether you adored his stubborn tantrums or quietly admired his romantic sincerity, there is no denying that Adam Sandler helped define the tone of the decade.
The1990swere a playground for extremes. Slapstick humor was ruling multiplexes,rom-coms were cheesy and earnest at the same time, and scripts did not shy away from blending wild plots with a dramatic finale. Sandler found himself perfectly suited to this landscape. He portrayed underdogs, troublemakers, and misfits who would fight the system one joke at a time. But it wasn’t just waterboys and wedding singers. There were some lesser-known ‘90s outings that kept Sandler at the front as well. So now, withtheHappy Gilmoresequel around the corner, it’s time to dig into every Adam Sandler movie from the 1990s.
10’Shakes the Clown' (1991)
Shakes the Clown
Set in the fictional town of Palukaville, whereclowns are a rivalrous subculture,Shakes the Clownfollows Shakes, played by Bobcat Goldthwait (who also wrote and directed), a birthday party clown spiraling into self-destruction and alcoholism. If losing out on a coveted gig to the psychotic Binky isn’t enough, he is framed for the murder of his mentor, Owen Cheese.
A Bizarre Clown-Gangster Comedy
Shakes gets help from his loyal clown friends Dink and Stenchy to go on the run, disguise himself as a mime, and uncover a conspiracy, with it all leading to a chaotic rescue and redemption arc. This is Adam Sandler’s earliest film role, and while he plays second fiddle as Dink, his presence brings a youthful energy to the ensemble and offers a glimpse into his future in the comedy scene.
9’Coneheads' (1993)
After crash-landing on Earth during a reconnaissance mission, Beldar and Prymaat Conehead (Dan Aykroyd and Jane Curtin) attempt to blend into suburban American life while waiting for someone from their home planet of Remulak to come and rescue them. They raise a daughter, Connie, who grows up embracing Earth’s culture and even falls in love with a local mechanic named Ronnie.
A Delightfully Odd Sci-Fi Comedy
When the rescue ship finally arrives for the Coneheads, Aykroyd’s character is forced to make a difficult choice, and battle with the monstrous Garthok on Remulak before returning to Earth, now with green cards. The cast ofConeheadsfeaturesSNLalums likeChris Farley, David Spade, Michael McKean, Garrett Morris, Jan Hooks, Kevin Nealon, and Phil Hartman, and Sandler, a standout, appears briefly as Carmine, a sketchy ID forger.
8’Mixed Nuts' (1994)
Mixed Nuts
Set on Christmas Eve in Venice Beach,Mixed Nutsfollows the misadventures of a small suicide-prevention hotline called Lifesavers, which is run by the well-meaning but overwhelmed Philip. As eviction looms, the office is flooded by visitors and the accidental death of their landlord sends the group scrambling to cover the incident up.
The Ideal Madcap Holiday Chaos
Featuring perhaps the best cast a ‘90s comedy could conjure up, which includes Steve Martin, Juliette Lewis, Madeline Kahn, Anthony LaPaglia, Rob Reiner, Garry Shandling, Liev Schreiber, Rita Wilson, Parker Posey, Robert Klein, and Steven Wright, the movie is complete with comical misdirection and manic proceedings. Sandler plays Louie, a weirdo with a ukulele. His role is small, but he’s seen serenading the group with offbeat songs every now and then.
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7’Bulletproof' (1996)
Bulletproof
Sandman’s Archie Moses is a small-time crook with a knack for stealing cars and smuggling drugs for Los Angeles kingpin Frank Colton. His best friend and partner-in-crime, Rock Keats, is secretly LAPD detective Jack Carter, working to bring the operation down. When a botched heist blows Carter’s cover, Moses flees, and months later, the two are forced to team up and testify against Colton.
A Curious Entry in Sandler’s Catalog
Bulletproofisa buddy action-comedythat pairs Adam Sandler and Damon Wayans in a partnership that is riddled with shootouts, betrayals, and unexpected twists. The plot is thin, and it gives them little to work with, but the actors share a chemistry that borders on absurd, which makes the film watchable. The gangster subplot, complete with corrupt police and a drug empire, gives the movie its edge.
6’Airheads' (1994)
Chazz, Rex, and Pip are the struggling rock trio “The Lone Rangers.” They are desperate to get their demo played on the radio, but after being rejected by every label in town, they are left with no choice but to storm a local station with squirt gums filled with hot sauce and trigger a hostage crisis. As the situation escalates, the band becomes a media sensation and draws the attention of fans and record execs alike.
Rock Rebellion Gone Wrong
Brendan Fraser, Steve Buscemi, and Adam Sandler form the trio that steers the film,Airheads, to a rebellious finale where they smash their instruments and the stage and dive into the crowd, earning a prison sentence and a triple platinum album. So it seems like it all worked out for them. Sandler’s Pip is the lovable, dim-witted drummer who delivers some of the movie’s most quotable lines and balances off Fraser’s angst and Buscemi’s cynicism.
5’Big Daddy' (1999)
InBig Daddy, Adam Sandler plays Sonny Koufax, a 32-year-old slacker living off a lawsuit settlement and avoiding all adult responsibilities. It doesn’t help that his girlfriend has just dumped him for an older, more mature man. When his roommate leaves for China, a five-year-old boy named Julian is dropped at their apartment, and Sonny impulsively decides to raise him to win back his girlfriend.
A Feel-Good Classic
While Sandler is best known for his broad, over-the-top comedic roles, his performance inBig Daddyshowcases his ability to bring depth and emotional nuance to the character. He’s peak Sandman in the film, equal parts immature and endearing. Directed by Dennis Dugan, the movie blends slapstick with sentiments, and while critics were divided, audiences embraced it, andBig Daddybecame Sandler’s highest-grossing film of the decade.
4’The Waterboy' (1998)
The Waterboy
Bobby Boucher is a 31-year-old socially awkward and emotionally repressed waterboy with a stutter, a heart of gold, and a mother who believes everything fun is the devil. After being fired from his job with the University of Louisiana Cougars, Bobby volunteers for the same role with the South Central Louisiana State University Mud Dogs. One thing leads to another, and Coach Klein recruits him as a linebacker, granting the team an unexpected winning streak.
A Quintessential Sandler Underdog Story
Sandler’s performance as the odd and sympathetic Bobby is the heart and soul ofThe Waterboybecause he brings his signature blend of physical comedy and genuine pathos to the role. His exaggerated voice and awkward actions could have easily become boring, but he rounds out the character with real sweetness. The film’s direction by Frank Coraci propelled it into a massive $190 million box office haul, which was no easy feat back in 1998.
3’Billy Madison' (1995)
Billy Madison
Adam Sandler plays the titular character, Billy Madison, a spoiled and lazy heir to a hotel empire. An overgrown manchild, he spends his days drinking, pranking, and hallucinating about penguins. When his father announces his plans to hand the company over to a worthy executive, Billy begs for a second chance. But the catch is, Billy must complete grades 1 to 12 in 24 weeks to prove himself capable.
Time Capsule of Sandler’s Early Success
Billy Madisonis notjust pure Sandler chaos, but also the one movie that truly launched his big-screen persona. It was a major breakthrough for the actor, and his performance is loud, juvenile, and unapologetically bizarre. Yet, it strikes a chord with audiences who accepted its offbeat charm, the silly voices, and the gibberish talk. Critics were harsh, but the movie has since gained cult status, especially among fans who grew up quoting every line.
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2’The Wedding Singer' (1998)
The Wedding Singer
The Wedding Singeris a romantic comedy set in the 1980s, and it follows the story of Robbie Hart, a wedding singer with big dreams and a broken heart. After being jilted at the altar by his fiancée, Linda, Robbie feels hopeless. That is until he meets Julia, a sweet waitress engaged to the arrogant Glenn Gulia. As Robbie helps plan her wedding, their friendship evolves into something more.
Sandler and Barrymore’s Irresistible Chemistry
Sandman dials down the slapstick and leans more into genuine vulnerability here, because his character is heartbroken. Heshares a palpable chemistry with Drew Barrymore, and their intriguing relationship becomes the beating heart ofThe Wedding Singer, a rom-com that ends with a grand gesture on a plane. Directed by Frank Coraci, the movie has that nostalgic ‘80s aesthetic with a funny narrative. It was a major critical and commercial success and still remains one of Sandler’s most beloved works.
1’Happy Gilmore' (1996)
Happy Gilmore
Happy Gilmorecenters around the titular character, who is a failed hockey player with a temper and a surprisingly powerful golf swing. When his grandmother’s house is threatened due to unpaid taxes, Happy enters the world of professional golf to win prize money, but his unconventional style clashes with the sport’s otherwise polite rules, and he’s forced to master the game without letting his rage control him.
The Most Absurd Sports Comedy
Happy Gilmoreis a showcase of Sandman’s unparalleled ability to inject even the most outlandish scenarios with a sense of genuine humor and heart. As Happy, he is brash and stubborn but ultimately impossible to look away from. Dennis Dugan directs witha brisk pace and irreverent tone, while Christopher McDonald’s Shooter McGavin delivers a memorable turn as one of comedy’s greatest villains. That said, it’s not just a sports comedy but a celebration of misfits and unbridled rage.
