Reel Toronto: Billy Madison
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Reel Toronto: Billy Madison

Toronto’s extensive work on the silver screen reveals that, while we have the chameleonic ability to look like anywhere from New York City to Moscow, the disguise doesn’t always hold up to scrutiny. Reel Toronto revels in digging up and displaying the films that attempt to mask, hide, or—in rare cases—proudly display our city.
The first of the Adam Sandler mega-hits, and one of the stupidest movies ever made: it’s Billy Madison! Oh, it may be one of the great, funny-stupid movies, but to paraphrase one of the movie’s funnier bits, you may feel dumber for having watched it, and may God have mercy on your soul.
Oh, and it was shot in and around Toronto.

The most prominent location is Oshawa’s Parkwood estate which we’ve seen in a kajillion things, like X-Men. It plays Billy’s mansion from the front…
…and even shows off its lovely gardens.
But its front gates must suck, because they drove all the way to King City’s St. Augustine Monastery to capture its picturesque front door, way up on Keele Street.
Hey! Isn’t that respected playwright, director, and actor Hrant Alianak? Yes. Yes, it is.
Billy enjoys hanging out with his pals (Marco! Polo!), and they have a bite at what used to be called C & W Burgers, and what’s now known as C & Dubbs, way out on Dundas Street East.
Right, so Billy goes back to school and he goes to several over the course of the film, so multiple local schools were used for filming. This one…
…including the rear yard, home of the famous dodgeball scene, is John Ross Robertson P.S. How great is this scene? So great that Adam Sandler really wanted the kids to cry when he really hurt them. Now, that‘s funny.
His high school, however, was mostly shot at Western Tech. You see the front…
…and the back. Some interior scenes were apparently shot at Northern Secondary
…but the auditorium scenes in the finale were shot back at Western Tech.
Hey! Isn’t that respected actor and Emmy winner Bradley Whitford of West Wing fame? Yes. Yes, it is. Amusingly, he also played a sleazebag in the Toronto-shot Adventures in Babysitting. This town must have a real soft spot in his heart.
At least there’s some Farley going on. He plays a bus driver who takes the class to a pioneer village–type place.
And, guess what? You know that classic scene where the kid pees himself and then Sandler also pretends to pee himself and you can’t help but love the big lug? Yeah, that was filmed at Black Creek Pioneer Village.
There you go: another proud moment in our cinematic history.

CORRECTION: OCTOBER 4, 2013: Following a great deal of discussion by several comments, we agree that the elementary school we did not identify, pictured twice above, is actually John Ross Robertson P.S. Also, thanks to those who pointed out the finale in the auditorium was shot at Western Tech, not Danforth Tech. We’ve corrected the information above.