Adam Sandler was fired from Saturday Night Live, despite being part of one of SNL‘s best casts. It’s a fact he joked about when he returned to host after 25 years in an “I Was Fired” monologue song. But the funnyman had the last laugh. He went on to found Happy Madison Productions, which has produced (and continues to produce) numerous movies, many of which he stars in. The movies were rarely (if ever) praised by critics, but it didn’t matter. Many of them were massive box office successes, thanks in large part to Sandler’s silly comedic antics and signature style.
Sandler went on to prove that he’s a talented actor beyond the comedy genre, starring in movies like Paul Thomas Anderson‘s Punch-Drunk Love, Uncut Gems, and Hustle. While he has been consistently delivering popular movies, from serious to animated fare, as well as Netflix films like You Are So Not Invited to My Bat Mitzvah, it was the 1990s that solidified Sandler’s position as a cultural comedy icon. Not all his movies from the decade were hits, but each played a role in making him one of the most successful comedy moviemakers and actors of that decade.
7. Deuce Bigalow: Male Gigolo (1999)
Sandler is known for working with his close friends, and Deuce Bigalow: Male Gigolo is one such project. It stars his former fellow SNL cast member Rob Schneider, who also wrote the movie. The sex comedy centers around the title character, a fish tank cleaner who causes serious damage to someone’s home while housesitting. In a desperate attempt to earn money to pay for damages, Bigalow decides to start working as a male prostitute. His journey takes him from hiring a pimp to pleasing his customers without actually having intercourse and even falling in love unexpectedly.
Despite how ridiculous Deuce Bigalow: Male Gigolo is, the movie was a box office success, ranking third in theaters behind only Toy Story 2 and The Green Mile in its opening weekend. This movie is a rare one on this list, as it was made by Sandler’s production company, but does not feature him in the cast. Keen-eared viewers will, however, recognize Sandler’s distinctive voice as a man walking by on the street who insults Tina, an extremely tall woman who is one of Bigalow’s clients. Deuce Bigalow: Male Gigolo is filled with typical gags and dumb jokes. For die-hard Sandler fans, while it isn’t his best work, it’s one that will make you laugh.
6. The Waterboy (1998)
A sports comedy with a predictable plot, The Waterboy stars Sandler as Bobby Boucher, an awkward man in his 30s working as a waterboy for a university football team. He’s constantly bullied by the big, brawny players, and finally gets fired for presumably disrupting the team. He takes a job as a waterboy for another struggling team. But this time, instead of letting the bullying happen, Bobby’s new coach urges him to stand up for himself. He does, and as it turns out, all those years of pent-up rage have turned Bobby into a fierce tackler. So much so that the coach decides to put Bobby on the team.
A hilarious story of redemption, The Waterboy also touches on protective parenting. Bobby’s overprotective mother, Helen (Kathy Bates), doesn’t want him to play, even faking an illness to stop him from doing so. Despite being criticized for its cheap gags and low-brow humor, The Waterboy was once again a box office success, and is one of Sandler’s key comedies in the ’90s.
5. Airheads (1994)
Sandler stars alongside frequent collaborator Steve Buscemi, as well as Brendan Fraser, as three members of a struggling rock band. In desperation, they do the unthinkable and hijack a radio station to get their demo tape aired. Airheads, the only film on this list that doesn’t come from Sandler’s own production house, was considered a failure in every respect, including both box office numbers and critics’ reviews. But in the three decades since, it is now considered a cult classic.
Airheads is worth watching for the incredible supporting cast alone, which includes the late Chris Farley, Michael McKean, Judd Nelson, Michael Richards, Ernie Hudson, David Arquette, and the late Harold Ramis.
4. The Wedding Singer (1998)
Sandler stars as Robbie Hart, a struggling wedding singer preparing to marry his girlfriend, Linda (Angela Featherstone). But when he meets new waitress Julia (Drew Barrymore), sparks fly. He is even more drawn to her when he discovers that her soon-to-be-husband, Glenn (Matthew Glave), is a terribly arrogant, cheating jerk who doesn’t truly care for her.
As a traditional rom-com, you can imagine where things go from here. But the sweet moments, combined with Sandler’s signature humor, make The Wedding Singer the type of rom-com couples will actually want to watch together. As the first of what would be many more collaborations between Sandler and Barrymore, The Wedding Singer could have been No. 1 at the box office had it not come out while Titanic was still in theaters. It’s one of Sandler’s best-reviewed comedy movies from that decade, and is a Valentine’s Day staple.
3. Big Daddy (1999)
Co-starring a young Dylan and Cole Sprouse as Julian, Big Daddy casts Sandler is in a fish-out-of-water scenario as Sonny, an irresponsible man in his 30s who’s suddenly tasked with caring for a five-year-old. The child is his roommate Kevin’s (Jon Stewart) biological son, and the mother leaves a note saying she can no longer care for him. With Kevin away in China on business, there’s no choice for Sonny but to step up. But he has no experience with kids,much less being a responsible adult.
What happens in Big Daddy is an adorable story about the growing bond between a hapless man and a precocious five-year-old. While Sonny is supposed to be parenting Julian, it’s the young boy who ends up teaching him much about life. Naturally, Sonny can’t seem to do anything right at first, but by the end, he is a changed man. Critics were divided on Big Daddy, but for anyone who has seen the movie, there’s no question that it’s a heartwarming comedy-drama that will tug at the heartstrings.
2. Billy Madison (1995)
A fan favorite, Billy Madison is an endearing comedy about the man-child son of a wealthy businessman who spends his days drinking and acting foolish with his friends. When his fed-up father tells him he’s handing his company over to his devious second-in-command, Eric (Bradley Whitford as a villain you love to hate), Billy springs into action. He’ll prove he’s worthy by any means necessary. Learning that his father bribed his teachers to ensure he graduated, Billy agrees to redo every grade and get his high school diploma to prove he has what it takes.
So begins Billy’s journey from kindergarten to high school, as he deals with all the growing pains of being a kid and a coming-of-age teen all over again. Despite the silliness of the movie, there are moments of tenderness, like when Billy sprays his pants with water to help a classmate avoid ridicule after he accidentally wet himself. Billy Madison received unfavorable reviews (a recurring theme with Sandler movies0 yet was No. 1 at the box office when it premiered. The movie, also common among Sandler films, has since developed a cult following.
1. Happy Gilmore (1996)
A cameo from Bob Barker and a supporting role by Carl Weathers? It doesn’t get much better than that. Throw in the absolutely hilarious rivalry between Sandler’s title character and the arrogantly preppy Shooter McGavin (Christopher McDonald), and this movie is pure comedic gold. Happy Gilmore is a wonderful sports comedy about the underdog. Failing at becoming a pro hockey player, Gilmore accidentally discovers that he has a talent for golf. Retired pro golfer named Derick “Chubbs” Peterson (Weathers) takes Gilmore under his wing, hoping to coach him all the way to the Tour Championship.
Gilmore is reluctant, but driven by the prize money, which he needs to help his elderly grandmother save her home. But winning won’t be easy for more reasons than lack of experience and finesse. The pompous McGavin believes he has the win in the bag and takes every opportunity to insult and rile up the rough-around-the-edges, temperamental Gilmore.
Happy Gilmore makes the otherwise quiet and subdued sport of golf invigorating. Gilmore brings the stereotypical tough hockey player attitude onto the green, which at first puzzles fans, but then has them excited to see what he’ll do or say next. How many times have you heard a golfer scream at the ball, asking if it thinks it’s too good for its home? Yes, he even gets into a fistfight with Barker, who plays himself. There’s so much to love about Happy Gilmore. It’s one of the most quotable Sandler films that you can watch again and again, and it never gets old.
