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Billy Madison

Adam Sandler is Billy Madison in Billy Madison. Tamra Davis (Half Baked) directs Adam Sandler in his first starring role. Billy must prove to his father that he is competent enough to take over the family business. The best way to prove his competence is to repeat first grade through his senior year in high school, spending two weeks in each grade. This wasn’t a box office hit, but it’s Adam Sandler’s best movie.

Billy Madison is a loser. A rich loser. He spends his days getting drunk and chasing imaginary penguins around his dad’s mansion. Billy is the heir to the Madison Hotel chain, but his dad doesn’t know if he can handle the pressure of running a Fortune 500 company. Billy proposes that he goes back to school to show that he can graduate without his dad’s help or influence.

Billy starts reliving his childhood two weeks at a time. He draws a blue duck with Miss Lippy in first grade. He falls for Veronica Vaughn (Bridgette Wilson), his third grade teacher, and he makes friends with Ernie and a few other students. Elementary and middle school is fun, but eventually Billy winds up in high school again. This time he isn’t as popular as the last time around and he makes amends with people he bullied in high school (like Steve Buscemi in an awesome cameo).

The villain of the story is Eric Gordon (Bradley Whitford), who stands to gain Madison Hotels if Billy fails. Naturally he tries to sabotage Billy, and when Billy finds out he challenges him to an academic decathlon to determine who takes over the business.

I am beginning to suspect a certain trend of happy endings in Hollywood movies, because Billy ends up winning even though he’s probably suffering from brain damage. Billy is not smart. He has occasional flashes of brilliance, but he’s not a smart character. He knows that there is no “w” in “couch” but still struggles to spell it correctly. He’s mean too. He picks on little kids and belittles them and makes no attempt to say sorry or rectify the situation.

There are some great supporting roles in this movie. Norm Macdonald stands out as Billy’s loser friend. He’s the kind of guy who steals thirty bagged lunches, lights bags filled with shit on fire, and has pickle races down store windows. Chris Farley plays an angry bus driver. He throws a banana peel out the bus window, and shots of the slowly decomposing peels become interspersed throughout the movie, before the peel leads to the demise of the O’Doyle clan.

There is a simple plot with a lot of random moments. A lot of elaborate sequences have no real bearing on the movie, most notably the opening chase of the imaginary penguin. There’s a sudden musical number, as inspiring as it is confusing. The movie doesn’t take itself seriously, but there should be more of a reason behind gags like that.

This is Adam Sandler’s best movie. Happy Gilmore is the only other candidate for his best movie. Sandler is not that funny. He is goofy. He makes weird noises and makes fun of lunch ladies. He’s not a great comedian, but he can turn a film into a vehicle for himself and that’s not easy to do. If you missed the ‘90s for whatever reason, you can watch this movie and catch up.

Critically Rated at 13/17

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