Adam Sandler has been quite polarizing for his entire career. These days however fans are either reminiscing on the days of Happy Gilmore and Billy Madison, or haters are ragging on Sandler's flops, such as Jack & Jill and his recent Netflix originals.
Nonetheless, no one can deny that Adam Sandler has come up with some pretty hilarious characters throughout his career. Here are Adam Sandler's 10 funniest characters.
Sonny Koufax (Big Daddy)
In Big Daddy, Adam Sandler stars as lazy, immature 30-something Sonny Koufax who unexpectedly fosters his roommate's 5-year-old son, Julian (played by the Sprouse Twins). Antics ensue as Sonny, still mentally a kid himself, attempts to provide for Julian and guide him on the right path.
Technically speaking, Sonny can cross the street without any handholding, but in many ways, Julian is more mature than he is, giving Sandler's character a plethora of silly but touching moments in which he finally becomes an adult.
Opera Man (Saturday Night Live)
Adam Sandler's days on Saturday Night Live birthed several iconic characters, some of which were even carried over to the big screen. One of Sandler's biggest SNL characters is Opera Man, who sings about the week's top stories during the show's Weekend Update segment.
Sandler resurrected the hilarious opera-singing, handkerchief-waving Italian for his return to SNL as host in May 2019, marking the first appearance of the character in 24 years.
Longfellow Deeds (Mr. Deeds)
Adam Sandler plays Longfellow Deeds in Mr. Deeds, a comedy about a small-town poet and pizzeria owner who inherits $40 billion from a long-lost relative. As the title pun suggests, Deeds is a kind-hearted man who loves to help others in need. He's so loving toward everyone he meets, even closed-off businessmen, and the cultural disparities make for great laughs everywhere Deeds goes.
In his home town, he'll carry an old man across the street or bring his homeless friend Crazy Eyes (Steve Buscemi) a free pizza topped with french fries and Oreos. When he steps into the billionaire world, his friendliness extends to other billionaires and housekeepers alike, giving us the film's funniest scene in which he tells his butler (John Turturro) to stab his frostbitten foot with a fire poker.
Billy Madison (Billy Madison)
In Billy Madison, the titular character (Sandler) must repeat all twelve grades of school for two weeks each in order to inherit his father's hotel empire and prevent it from being taken over by malicious businessman Eric Gordon (Bradley Whitford). Even though he's a spoiled, deviant, rich kid, Billy has no problem letting his guard down around classmates.
He connects with the kids because he's still young at heart, but his life experience also allows him to help them through tough times and warn them about the downsides of adulthood. In one scene, a classmate pees his pants, so Billy splashes water on his pants and tells everyone that wetting yourself is cool, leading to a whole busload of smiling kids with wet pants. Billy's unwavering ability to be himself at all times brings endless belly laughs in this 1995 classic.
Canteen Boy (Saturday Night Live)
Another one of Adam Sandler's recurring SNL characters is Canteen Boy, a naive scout who is often the butt of others' jokes. In one particular sketch, Sandler manages to outshine Alec Baldwin as he makes sexual advances towards him.
Sandler is responsible for the hilarious discomfort throughout the sketch and, to his credit, doesn't break character as much as you'd think he would with Alec Baldwin's tongue down his ear.
Nicky (Little Nicky)
Part of what makes Adam Sandler such a great character actor is the way he changes himself physically to morph into each character. As Nicky, one of three spawns of Satan, Sandler maintains a playfully off-centered smile throughout the film (we learn early on that his face and speech were disfigured when his brother hit him with a shovel).
Nicky is the only one of Satan's sons who has a good heart and, most importantly, a sense of humor. Seeing the Nicky character interact with Earthlings and a vulgar talking bulldog as he searches for his brothers and asks people to "get in the flask" is what makes Little Nicky one of Adam Sandler's most amusing films.
Brian (Saturday Night Live)
Brian, host of The Denise Show, is by far Adam Sandler's funniest Saturday Night Live character. He's a heartbroken man who's still obsessed with his ex-girlfriend Denise, and wavers back and forth between idealization and resentment. Sandler gives the character an unpredictable rage, speaking calmly about his ex while fidgeting in anger by bouncing his leg and rubbing his hands together, until ultimately reaching the segment where he "loses it," making the audience laugh so much Sandler can't help but smile himself.
The Denise Show also features guests like Chris Farley —a neighbor who knows Denise and stops by to share his thoughts on the relationship—and hilarious segments like calling Denise just to hang up on her.
Bobby Boucher, Jr. (The Waterboy)
The Waterboy stars Adam Sandler as Bobby Boucher Jr., a sheltered, socially awkward Southern boy who lives with his mother (Kathy Bates) and works as a water boy for a football team that picks on him. Though he switches teams and becomes a successful linebacker by the end of the film, Sandler wears an uncomfortable, uncertain smile in each social interaction, allowing the audience to laugh along with his discomfort.
Bobby is also more intelligent than meets the eye, and Sandler whimsically plays him like a child delivering surprisingly clever lines.
Robbie Hart (The Wedding Singer)
In The Wedding Singer, Adam Sandler gives us what we love about him the most—a balanced diet of music and comedy—as Robbie Hart, a wedding singer in the 1980s. We follow his character through heartbreak, which triggers classic Sandler rage and songs like "Somebody Kill Me." Robbie feels like a parody of classic John Cusack roles—sad, music obsessed, but sillier and more optimistic.
As the film progresses, he falls in love with Drew Barrymore's character and Robbie's humor becomes more light-hearted, along with the songs he writes ("Grow Old With You" is a gem). To top it all off, the film is full of in-your-face 80s references, like Robbie emotionally quoting Madonna's "Material Girl."
Happy Gilmore (Happy Gilmore)
Nobody does angry funny like Adam Sandler, and no character has more anger in him than Happy Gilmore. Sandler's outbursts are unpredictable yet well-timed, leaving the audience in a state of comedic suspense from start to finish.
As rejected hockey player Happy competes in the Pro Golf Tour to save his grandmother's house from being repossessed by the IRS, his emotions ramp up, and his explosions prove to be a hilarious and cathartic viewing experience.