Adam Sandler’s Best Movie Is Incredibly Hard To Watch

Billy Madison has a simple premise, and is basically the ’90s version of Rodney Dangerfields’ Back to School. The story centers on its titular character (Adam Sandler), a juvenile, day-drinking, obnoxious slacker on the wrong side of his 20s who has coasted through his entire life up to this point. Billy’s father, Brian (Darren McGavin), the founder and owner of Madison hotels, doesn’t believe that his son is capable of taking over the company when he retires, and is on the verge of letting his vice president, Eric Gordon (Bradley Whitford) take over the business.

Given how poorly Billy performed in school on his first go-around, Brian gives him one last chance to redeem himself by challenging him to go back to grade-school and prove that he’s intelligent enough to take over the family business.

As idiotic as the premise to Billy Madison sounds, it was the perfect vehicle for Adam Sandler to do what he did best at the time, which was be wholesomely obnoxious, but with an actual big-studio budget behind him to fully realize his vision in the most hilarious way possible.

Going all the way back to first grade in order to prove his worth, Billy Madison thinks he’ll be able to breeze through primary and secondary school and take over the business, but there are complications along the way. Most notably, he becomes smitten with his third-grade teacher, Veronica Vaughn (Bridgett Wilson), who has similar feelings of affection toward him after seeing how well he gets along with her students.

Furious with Billy Madison’s willingness to pursue his education, Eric decides he needs to sabotage his efforts by spreading lies that will make Brian doubt the legitimacy of his son’s passing grades. Since Eric believes that Madison hotels rightfully belongs to him, he resorts to blackmail, extortion, and humiliation to get what he wants. Knowing that he’s an easy target, Billy uses whatever limited mental resources he has to try to reclaim his dignity as he puts his head down and sets out to accomplish what nobody, not even his father, thinks he’s capable of.

Though Billy Madison is very much an exercise in over-the-top toilet humor and jokes that most of us would consider to be “low-hanging fruit,” there’s a clear source of conflict, a love interest, and an extremely unlikable antagonist, all of which are the necessary components for solid story-telling. As Billy works his way through high school, he learns the hard lesson that there’s more to life than just screwing around, and that nobody will take him seriously if he doesn’t even take himself seriously.

Beneath the film’s veneer of slap-stick humor and Adam Sandler’s incessant screaming, there’s also a story that miraculously somehow has enough heart to make it universally appealing to people who just want to have fun watching a light-hearted comedy about a grown man going back to grade school.

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Billy Madison isn’t a clever movie, or even an original idea, but thanks to small supporting roles from Norm Macdonald, Chris Farley, and Steve Buscemi, it doesn’t need to be. All the mechanics for a solid comedy fall into the right place, and make for a memorable outing that rightfully deserves its massive cult following and extreme quotability.

Though it’s unfortunate that you can’t easily stream Billy Madison with a subscription to one of the many services that we’re all paying for, I’m confident in saying that it’s worth the $3.99 price-tag on Apple TV+ if you want to take a trip down memory lane.