Bad Movies We Love: Billy Madison

I won't see Adam Sandler's new joint Jack and Jill because I'm a thinking organism, but my defiance is worthless: I've already watched Billy Madison enough times to line Opera Man's pockets with box office dollars for life. He already wins. The mid '90s marked a renaissance in vulgar, idiotic kid comedies (Dumb and Dumber, Tommy Boy, etc), and Sandler's breakthrough Billy Madison -- which barely earned back its $20 million budget -- remains the best of the bunch. Let's jump back in time and yell "O'Doyle rules!" at this loud old gem.

Billy Madison is the rather quaint story of a deadbeat twentysomething (Sandler), who is only allowed to take over his father's (Darren McGavin) hotel business once he repeats elementary, middle, and high school in the span of 24 weeks -- two weeks per grade. This means Billy has to win a second grade spelling bee, survive junior high terrors, and pass 10th grade science tests with flying colors. Though he completes the tasks, scheming money-grubber Eric Gordon (Bradley Whitford) challenges Billy to a battle of wits at film's end to seal the deal. Can spoiled rich kid Billy get off his innertube and prevail?

As you may have gleaned, this is a stupid movie. In the words of the film itself, "Everyone in this room is now dumber for having listened to it." But it overrules your better judgment, tests your immaturity at every turn, and manages to be ridiculously, often maniacally funny. These five moments from Billy Madison prove that even if our movie hero is an obnoxious halfwit, there's still room for weird, dark humor to subvert the kid comedy mold:

5. Billy's musical fantasia

Adam Sandler movies are known for their dream sequences -- the sight of Julie Bowen brandishing beer steins in Happy Gilmore is one I won't soon forget -- but Billy Madison tops them all with a lip-synced, Broadway-style musical number that Ryan Murphy might envy (or hate, better yet). After Billy's third grade teacher-cum-girlfriend Veronica (Brigitte Wilson-Sampras, who also costarred in the famous Bad Movie We Love I Know What You Did Last Summer) slugs Billy for slacking off, he thanks her for waking him up with this magnificent opus. "Thank you, Veronica, for beating the shit out of me" is the new "This is the dawning of the age of Aquarius," and it's glorious watching the sun to shine upon Billy and his burnout friends with the power of a thousand hippie anthems.

4. Steve Buscemi jump-starts a career in creepiness

Billy Madison is dark and daring around the edges. Take for instance Steve Buscemi's unbilled performance as Billy's old high school foe Danny McGrath; Billy phones Danny to apologize for terrorizing him as a teenager, and Danny nonchalantly accepts. Then, after putting the phone down, Danny leans over and crosses Billy's name off a hit list. Extreme! And it only gets chillier once Danny coats his mouth with pink lipstick right after. What a fine prelude to the grim woodchipper drama that Buscemi would give us soon after Billy Madison.

3. To pee or not to pee

I was surprised to find upon reviewing that Billy Madison is a very sweet movie too. Billy sympathizes with his classmates of varying ages, and if he's not pummeling them with dodge balls during recess, he's often acting as their buffoonish, but loving babysitter. When his pal Ernie wets himself on a field trip, Billy announces that "peeing your pants is cool" and makes a fad of the accident in front of the class. All I'll say is an ensuing line about Miles Davis is just about the funniest thing in the movie, or ever, or forever. I can't help it. Brings new meaning to the term "Bitches Brew."

2. Our Miss Lippy

Speaking of bizarre characters: Billy's first-grade teacher is a loopy, pigtailed grownup named Miss Lippy. She's as suspiciously perky as any daycare provider, but Billy Madison has the guts to address her sinister pep with freaky detail. When Billy comes in early from recess one afternoon, he discovers the giddy Lippy dancing erratically to sitar music like an acid-dropping grandmother at Burning Man. Later, Billy finds her covering her face in glue. Maybe my own childhood curiosity about the weirdness of smiley people is coming into play here, but I swear this gushy lady is funnier than 100 percent of Caddyshack.


1. Billy fields "the ultimate insult"

When Billy faces off in an "academic decathlon" against Eric at film's end, a moderator asks him to compose an essay answer to a question about the Industrial Revolution. At first Billy is clueless, but soon he pieces together an impassioned response that references one of Miss Lippy's prized children's books -- The Puppy Who Lost His Way by supermodel Krissy Taylor (who literally died months after this movie's release). His answer is thorough, but the moderator -- who, so far, has deadpanned that his wife is a "dirty, dirty tramp" -- tears down Billy's moment of power with the most damning, hilarious monologue about failure I've seen since Gene Wilder barked "Good day, sir!" during Willy Wonka and the Chocolate Factory. Perhaps I need to retake kindergarten myself, but this is so much funnier than it has any right to be. May God have mercy on my soul.

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  • Noah James says:

    I used to LOVE this movie. LOVE it. So awesomely stupid. However, my love for it lessens with every movie he re-uses the man-child voice. "Jill" is just the latest character to use it.

  • Jake says:

    Shouldn't this be under the category, "Good Movies We Love"?
    This movie is just plain awesome. Bad movies we love would be more something like Black Belt Jones or similar.
    If this was an example of a bad movie, then almost everything that the classic comedians did could be in that category too. The entire oeuvre of The Three Stooges, most of the stuff from The Marx Brothers, and most of the Abbott and Costello movies. I think comedy should be rated on its ability to make one laugh, and not on how the plot or characters compare to more serious Oscar bait and art films. Little known fact: Comedy is much more difficult to do consistently than drama. If you want proof, use Billy Madison himself, Adam Sandler. You guys noted that no one wants to see this Jack and Jill movie. Is it because Adam Sandler has become stupid over the years? No. Comedy is just plain difficult because it has to stay fresh.
    Maybe it's time to start a new category, "Movies We Love."
    Side note: I wish we had a better way to honor the hard work of good comedy. Because the Oscars turn their nose up at it, but a lot of best picture winners were a walk in the park to make compared to Dumb and Dumber, Happy Gilmore, or Ace Ventura.

  • Sarah says:

    I'm way late on this one, but I'll never get over Chris Farley in this movie. "That Veronica Vaughn is one piece of ACE! I know from experience." "No you don't." "No, no, no I don't." Okay I'll stop. But seriously. Amazing.

  • Dan Jindahala says:

    I think this should be filed under "Bad Movies We Hate".

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