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Billy Madison (1995)
Adam Sandler’s first foray into headlining a major motion picture proves to be one of his most successful outings. Billy Madison is a complete screw up with a very successful father, so when the time comes for Papa Madison to hand off the reigns of his multi-million dollar hotel industry, Billy is shocked that he isn’t dad’s first choice. Negotiations are made, and it is decided that Billy must go back to school and repeat grades K-12 to prove that he has what it takes to run the family business. If Billy succeeds, he gets the business. If Billy fails, the company goes to the evil Eric (Bradley Whitford), a long-time employee of Madison Hotels. The film is sophomoric and extremely stupid, yet its heart is in the right place and it stands the test of time as being one of the most re-watchable comedies of the 90s. Cameos by Chris Farley and Steve Buscemi add to the zany tone of the film. Billy Madison is still one of Sandler’s most beloved movies and also deserves mention because it put him on the map as a certifiable comic star.
Happy Gilmore (1996)
Another early fan favorite of Sandler’s is this sports comedy about Happy Gilmore, a rejected hockey player who learns to take out his rage on the golf course. He ends up playing golf in order to secure that his grandmother doesn’t lose her home, as the large paychecks he earns aim to help keep granny out of a nursing home run by a sadistic Ben Stiller. Standing in Happy’s way is the cocky Shooter McGavin (Christopher McDonald), a golf pro with a vendetta against Happy and with a personality akin to dog poo. The film is full of classic bits, including the “Meesta! Meesta” Lady, a ferocious fight between Happy and Bob Barker, and a hand-chomping alligator. Happy Gilmore is similar to Billy Madison in rewatchablilty, as well as comedic tone. The film is very, very funny and represents the beginning of Sandler’s box office stronghold.
The Wedding Singer (1998)
Sandler’s best film is this sweet, tenderly romantic comedy in which he pairs with Drew Barrymore for the first time. Robbie Hart (Sandler) is a wedding singer who believes in true love, yet is left at the altar by his awful girlfriend Linda (Angela Featherstone). He works with Julia (Barrymore), a lovely waitress engaged to Glenn (Matthew Glave), who cheats on her and has the unfortunate last name of Guglia. Julia asks Robbie for help planning her wedding, and soon sparks begin to fly between the two. Sandler tones it down to play a mild-mannered romantic in the film, and proves that he can play sensitive as well as he can play immature. The ending to The Wedding Singer is one of the most applause-worthy endings of any romantic comedy, as it presents an adorable cap to a film that is unabashedly cute. The film takes place in 1985, and it does a wonderful job at capturing the decade through music and tone. The Wedding Singer is the most satisfying film Adam Sandler has ever made, and it presents a narrative that dares viewers not to smile.
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