9. Billy Madison

Rolling Stone

 

Adam Sandler had a knack early in his career for playing immature, responsibility-free cretins. Billy Madison showcases his capacity for such a character quite well. In order to inherit his father’s company, Sandler must repeat his education — going from kindergarten to 12th grade. For a trust fund kid in a 30-year-old’s body, this seems rather plausible, doesn’t it? All the same, this film holds tons of nostalgia for anyone growing up in the ’90s. Cameos by Steve Buscemi and the late Chris Farley give the film even more comedic value.


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