Adam Sandler has gone from Saturday Night Live performer to one of the most bankable stars in the world. His comedies have rarely been critically-acclaimed but audiences always turned out for them and seemed to love the wacky characters he would come up with.
Not all of Sandler’s characters are beloved classics, but he usually seems to go pretty big when creating them, for better or worse. Some can be laugh-out-loud hilarious while others can be downright obnoxious. Even his well-received dramatic characters can be pretty outrageous. Here are Adam Sandler’s weirdest characters.
Happy Gilmore (Happy Gilmore)
Happy Gilmore is one of Sandler’s most popular characters in one of his most popular movies. Happy is a rage-filled young who dreams of becoming a hockey player, despite having very little talent. However, to his surprise, he finds that he is a natural golfer.
As you can imagine, an aggressive and violent man like Happy doesn’t exactly fit into the more sophisticated world of professional golf. Happy stands out for his unorthodox approach to the game, due to the fact that he chooses a homeless man to be his caddy, and that he gets into a fistfight with Bob Barker.
Longfellow Deeds (Mr. Deeds)
Sandler was probably the last actor you would imagine starring in a remake of the film Mr. Deeds Goes to Town. However, Sandler managed to bring his own low-brow humor to the story of a small-town man who learns he has inherited a vast fortune from a distant relative.
The entire movie is meant to be a fish-out-of-water tale with Sandler being the kind and thoughtful country boy who is transplanted into the crazy world of New York City. Though Deeds is a good guy, he is not without his oddities such as his habit of getting into fights and his completely black foot that has no feeling.
Jill (Jack And Jill)
Sometimes Sandler’s films sound like they are just his way of seeing how silly a concept audiences will take. Jack and Jill finds Sandler playing a successful advertising executive who gets an unexpected visit from his obnoxious sister, also played by Sandler.
This kind of movie seems inevitable in Sandler’s career and the results are as cringe-worthy as you might expect. Jill is a loud, oblivious and brash person who means well but can’t help but screw everything up. Aside from a ridiculous wig, Sandler makes no effort to convincingly play a woman.
Barry (Punch-Drunk Love)
As much as critics have torn apart Sandler’s movies in the past, they have also admitted that he is a pretty exceptional actor when he wants to be. Punch-Drunk Love was the first time Sandler played a more dramatic role as a lonely man with suppressed feelings who falls in love with a girl.
Sandler is sensational as the quiet and self-conscious man who is prone to wild outbursts. It is a role not dissimilar to other characters he plays, but with a lot of added depth and vulnerability. From his interaction with his overbearing sisters to his awkward phone-sex conversations to his unique pillow-talk, this is one of Sandler’s most fascinating characters.
Sandy Wexler (Sandy Wexler)
Sandler’s partnership with Netflix was a genius move for both parties as his comedies are the kinds of movies that you can put on at home but don’t necessarily want to go to the theater to see. While some have been dismal, Sandy Wexler gave us one of Sandler’s more charming characters in recent years.
Sandy is a small-time show business manager who cares so much about his clients but is a little oblivious to the business side of things. His nasal voice and tired catchphrases feel like a typical Sandler character, but his charming naivety makes up a likable oddball.
Billy Madison (Billy Madison)
Billy Madison is another of Sandler’s classic characters and one of the best examples of how his humor can work on the big screen. Billy is a lazy, spoiled, and hard-partying son of a hotel magnate who goes back to redo his entire school career in order to inherit the family business.
Sandler’s silly voices don’t always work in movies, but here they are surprisingly hilarious. Billy spends his days drinking and chasing imaginary penguins while his time in school is even more outrageous.
Donny (That’s My Boy)
That’s My Boy partnered Sandler with fellow SNL standout Andy Samberg. Despite the potential of that pair, the movie was a misfire. Sandler plays the deadbeat dad of Samberg who comes back into his son’s life right before his wedding.
Donny is a mess of a character, sporting a thick and ridiculous Boston accent and a pretty disturbing backstory. He is an annoying, vulgar and deeply inappropriate man-child who happens to be good friends with Vanilla Ice.
Zohan (You Don’t Mess with the Zohan)
You Don’t Mess with the Zohan is one of Sandler’s more underrated films. Though far from perfect, it is an entertaining and silly comedy with Sandler giving a great comedic performance as Zohan, an Israeli soldier who dreams of becoming a hairstylist in America.
The movie plays with reality as Zohan defies logic and science with some of the things he is able to do, such as control his severed hand and put push-ups without using his arms. He also has a penchant for sleeping with older women and has an intense passion for disco.
Bobby Boucher (The Waterboy)
There are two prominent themes that permeate through Sandler’s work, sports movies and characters who hit people. The Waterboy manages to combine the two pretty effectively. Sandler plays Bobby Boucher, a simple-minded man raised by his overbearing mother and working as a waterboy for the local college football team. He is soon recruited after showing his rage-fueled tackles.
Boucher is an innocent young man who doesn’t make it out into the real world too often. He lives life based on his mother’s unusual teachings. Though he is mostly kind-hearted, when pushed, he can be pretty terrifying.
Nicky (Little Nicky)
Little Nicky finds Sandler playing the timid and awkward son of Satan. After his more mischievous brothers leave Hell to start trouble on Earth, Nicky must go bring them back.
Sandler is doing a whole lot of weird stuff with this character with mixed results. He has grease-slicked hair, a distorted face from getting hit with a shovel and a whispery voice. The whole routine makes Nicky his most off-the-wall character who can get pretty annoying over the course of an entire movie.
