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Wait, Is That Insult In Billy Madison Even Smarter Than It Sounds?

Billy Madison is a 1995 comedy about young man with an easy life who finds himself facing a tough challenge in order to keep that life. Hated by critics but still (astonishingly) a box office success, it firmly established the acting path and tone for the film’s star.

First, the story. After Billy (Adam Sandler), an obnoxious, self-centered party-boy, is deemed unfit to inherit the family’s Fortune 500 hotel chain due to his behavior and lack of business skills, his father stipulates he must complete grades 1 through 12 (each grade in two-week intervals) again in order to be considered. This pits him against Eric Goodwin (Bradley Whitford), a career-motivated yes-man and employee of Billy’s father who has eyes on the prize.

Billy Madison
Billy Madison, 1995 ©Universal Pictures

Directed by Tamra Davis, and written by Sandler, Billy Madison is a painfully unfunny film that starts with a grown, inebriated man chasing a giant penguin and goes nowhere from there, though admittedly, this is the intent, with a kind of gleeful celebration of its immaturity and vulgarities that found some appeal with Sandler fans but marked the beginning of a troublesome trend in his films that he still refuses to break from (aside from one brilliant turn in Punch-Drunk Love). Using the paper thin plot, the “story” is just an excuse for a string of senseless sketches that sees the dimwitted Billy, who in every right should miserably fail, turn it around, get the girl, and succeed in the most illogical way.

The thing about Sandler and company is their almost blatant refusal to cater to the critical crowd, producing movies seemingly more intent on breaking the expected than conforming to the standards, but of course, that in itself creates its own dynamic destined to become routine. While Sandler films earn mostly big money at the box office they have all settled at the bottom of the review pool. Billy Madison is an overwhelmingly bad film that somehow became a hit, but like every movie, good or bad, has one great moment.


Forced into returning to school to earn his way back into inheriting the company, the 27-year-old Billy actually goes to school, starting in grade one. Eventually he attends a class of third-graders where he instantly becomes attracted to the teacher Veronica, Bridgette Wilson. She resists at first, but soon finds herself smitten by his childish charms. Meanwhile, Billy is passing the grades and completing the challenge with few problems. Well, for Billy anyway. Cursive is still an issue. This distresses Goodwin, who will lose his chance at being named successor to the fortune if Billy graduates. He hatches a plan with the school principal that will derail Billy’s efforts. If you haven’t figured it out, he’s the bad guy. And apparently enjoys imbibing his own urine.

Billy Madison
Bradley Whitford (Billy Madison, 1995)

As luck would have it, all of Billy’s schoolmates stick up for him and Billy gets a second chance but this time, instead of returning to school, he challenges the slippery Goodwin to an academic decathlon to be held at the school. Goodwin accepts thinking it should be an easy win.

With a wild variety of categories, the contest is arranged and the two participate in a string of events in different classroom and venues, from academic achievements in math and science, to home economics tasks like baking, to musical performances and acting skills, each ending with increasingly lunacy. At one point, Goodwin literally falls to the floor enveloped in a huge swath of fire as Billy laughs at him. Because full body immolation is so funny. Eventually, they come to the final event with Billy miraculously leading by a single point. The final portion of the contest is a Jeopardy!-like quiz and the two men take their places on the school auditorium stage with the student body in attendance, along with Billy’s father and Veronica (who spends the entire film overtly sexualized).

Billy Madison
Bridgette Wilson (Billy Madison, 1995)

Billy is given the first topic, a question about how the industrial revolution changed the modern novel, needing to discuss and cite specific examples. Naturally, Billy has no idea what the question is about or how to answer it, but the audience cheers him on, trying to get him to give it a shot. So he prattles on about a children’s book he read in class about a puppy lost in the woods, hopelessly connecting that with the topic. When it garners no response, he simply incites the crowd with a school football chant.

This doesn’t impress the already exacerbated judge though, played hilariously by James Downey, who lets roll one of the greatest insult lines in comedic film. It goes like this, but don’t pretend like you don’t already know it by heart:

Billy Madison

Now, why is this so important, other than it being the only funny moment in this ‘comedy’? I hesitate to use the word clever in describing anything about this movie–or most of Sandler’s work–but this single moment does do something right. The cliché in underdog films is always having the hero learn to overcome the film’s climactic hurdle by applying the knowledge and experience gained throughout the story. It’s a trope of the genre. Think of 1984′s The Karate Kid, a classic example where a young man spends the duration of the film washing and waxing a car and painting a fence not realizing until the end that he’s actually learning karate.

Here, we watch Billy attend grade school classes and learn a number of life lessons from his young classmates and when it comes to the big showdown against the bad guy at the end, we expect it’s all going to come together and he’ll become the better for it. But that doesn’t happen. Billy is, like nearly all of Sandler’s characters, unteachable, a paragon of dimwittedness that succeeds only by contrived luck and charm. The movie even tries to trick us into believing this is the moment when Billy ‘gets it’ and will win the contest with his newly-acquired skills. The music shifts, the camera slows, Billy holds the microphone with authority–it’s classic setup, but in a surprise move, he utterly, spectacularly fails. The rug is pulled out from under us. That’s actually pretty smart and reveals how this movie could have taken this to the next level. You think it does?

Of course not. That great moment leaves the filmmakers with an opportunity and they might have had Billy fail completely and end up having to actually earn his education and the respect of Veronica, and maybe generate a lifelong lesson for viewers. But alas, no. Instead, they wholly (and even disturbingly) squander this chance with a gun battle in the auditorium. What? It’s a loathsome ending to a dreadful film. Still, one man’s reply to what amounts to a perfect criticism of the film entire, stands as this movie’s one great moment.

Wait, Is That Insult In Billy Madison Even Smarter Than It Sounds?


Director: Tamra Davis
Writers: Tim Herlihy, Adam Sandler
Stars: Adam Sandler, Bradley Whitford, Darren McGavin, Bridgette Wilson-Sampras