The Wild Cartoon World of Billy Madison


It starts with a giant penguin. 

Adam Sandler was already a comedy star by the time Billy Madison rolled around in 1995, thanks to a run on Saturday Night Live and films like Airheads, but something was still missing. Yes, he was a star, and he was on the rise, but he wasn’t Adam Sandler yet. With Billy Madison, which he starred in and co-wrote, Sandler delivered something career-defining, and it all goes back to one moment with a penguin.

The penguin in question appears just minutes into Billy Madison‘s opening sequence, which establishes the title character (Sandler) as a spoiled rich kid with nothing better to do all day than get drunk by the pool at his father’s (Darren McGavin) sprawling estate. It’s that estate, and Billy’s place in it as a manchild who’s never cared about anything, that forms the backbone of the film’s plot, but as with so many Sandler movies, the plot is just a framework on which to hang the real draw. When the penguin appears, we get a better sense of what that draw is, and why Billy Madison still stands out among Sandler’s massive comedy filmography. 

For More on Adam Sandler:
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Adam Sandler Accepts Mark Twain Prize for American Humor
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Why Billy Madison Remains One of Adam Sandler’s Best Movies

See, while the penguin is framed at first as a drunken hallucination, part of Billy’s endless party life, it becomes clear very quickly that it’s also just the tip of a very big iceberg of weird, anarchic comedy that makes Billy Madison hold up as one of the best, and funniest, things that Sandler has ever produced.

As we’ve already discussed, the framework for this story is sort of typical 1990s comedy fare, and the kind of hooky hijinks that came to define much of Sandler’s output for a very long time. It’s simple: Billy wants to take over his father’s hotel empire, but he’s told that he’s too incompetent to be trusted. He’s also told that he never actually made it through school under his own power. He just got by because his father bribed his teachers. Hoping to prove to his father that he can be a real adult, Billy takes on a wild gauntlet in which he’ll cover each grade of school in two weeks, graduate all over again, and therefore earn his father’s trust. 

It’s easy to see the comedy at work in this premise, particularly when you throw in Bradley Whitford as Eric, the executive who was supposed to take over the company before Billy decided he wanted to make a run at it. You’ve got a goofy concept, a villain, and a manchild trying to prove he can be a grown-up. It feels like a thousand other comedies. What sets it apart is what Sandler, co-writer Tim Herlihy, and director Tamra Davis do next. 

Right away there’s a sense of bigness, of outsized privilege and opportunity, that exists in Billy’s life. He is, after all, a rich kid who’s never known anything but a life in which he can have anything he wants, whenever he wants it. That means he never had to really grow up, yes, but it also means that he can essentially engineer any scenario he’d like at will, whether that means chasing a hallucinatory penguin with a golf cart, dropping flaming bags of poo on porches with his friends, or constructing an elaborate “study tent” in the backyard so he can remove himself from the world. Billy’s life is one without any real limits, and the film embraces that to great effect.

Then, Billy Madison goes further, and explores what happens when it takes basic tenets of civilized life, social systems, and even sheer reality and warps them the way Billy is able to warp the circumstances of his life. Yes he’s a rich kid who can throw a massive party every two weeks at will, but in this film’s world he’s also a guy who can somehow launch a weird musical number out of nowhere in a film that doesn’t otherwise suggest such things.

And then, somehow, that sense of strange re-engineering of the world around him becomes infectious, giving us loads of little background moments that add to the weirdness. Billy’s teacher paints her eyes with paste for some reason. A clown that seemingly died in a fall weeks earlier comes back to life and sings. Then, of course, the penguin returns and seems able to interact with other characters despite being a hallucination.

All of this means that Billy Madison is, even to seasoned viewers who’ve watched it more than once, a film that retains an air of the comically unpredictable, a sense that everything in every frame is somehow part of a cartoonish world that just gets weirder with each passing moment. That makes it one of Sandler’s best and boldest comedic efforts, almost 30 years after its release.

Billy Madison is now streaming on Peacock, alongside every season of Saturday Night Live.



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