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.

Is it an exaggeration to say that without the Distillery District there would be no Hollywood North? Um, probably, yeah. But still, they've shot so many movies there you would hardly believe it!
You can see a list of productions here, but you have probably watched a zillion movies like Undercover Brother (above) without even realizing it was your photogenic, friendly, neighbourhood gentrified arts district.

First, a bit of basic history: from 1881 to 1990, they actually distilled stuff in the Distillery District. Yup, the fine folks at Gooderham & Worts put out whiskeys and other yummy goodies in a remarkably preserved set of Victorian buildings and streets. (They also built several other local landmarks, including the Keg Mansion on Church Street.)
It was the biggest distillery in the world for a time and, so the legend goes, accounted for 50 percent of our federal government's tax revenues. They were bought by Hiram Walker, but after they closed, the versatile, old-school neighbourhood became a prime location for local movie shoots—the second most used location outside of Hollywood, apparently.
In 2001, Cityscape developments realized that whereas most Toronto history gets torn down, here was a chance to actually preserve some and to sell some Segways, Dale Chihuly sculptures, and cafe lattes in the process.

Undercover Brother is just the start of the district's Hollywood heritage, of course. With its gritty, un-Toronto appearance, the district has occasionally filled in as The Bad Part of Town in flicks like Half Baked.

The same applies to the Blues Brothers 2000, which needed some grit in its feeble attempts to make Toronto look like Chicago. That film also features the now departed Canary Restaurant, which once operated just east of the district. It can also be seen in The Long Kiss Goodnight.

One of the most recognizable buildings—and the oldest on site—is the limestone Stone Distillery, visible in the background of this shot from critical non-fave Short Circuit 2.

You can also see it here, playing a penitentiary exterior in the better-received Chicago. Today it's home to numerous art galleries. We don't believe everything Wikipedia says, buuuut apparently the building was also used for the shoot of Marilyn Manson's "The Beautiful People" video. Since we know the director was Toronto's Floria Sigismondi, we'll give them the benefit of the doubt.

This shot of the Callahan Auto Parts factory in Tommy Boy also has the building on display. You also can't miss the distinctive tower of the cooperage, where the whiskey barrels were made.

There's also a nice "main street"-type shot where you can see the Pure Spirits Building on the right.

Its industrial look is also used to fine effect in Cinderella Man, where it serves as the gates to the New Jersey dockyards.

One of its coolest film appearances is in the opening scenes of X-Men, where it plays a Nazi concentration camp. The smokestack of the otherwise innocent Boiler House is portrayed in a more chilling light, and you can see what some rain, smoke, and lighting can do.

Newsstand: November 9, 2009
Oh awesome. I didn't know the camp in X-Men was also a Toronto set.
I much prefer this approach - taking a single neighbourhood and showing how it has been featured in multiple films - as opposed to the single-film method (although that is mostly because I haven't seen most of the films you've featured).
I actually prefer the single film approach, though this entry makes for a nice summary. With the neighbourhood approach I feel like you'd end up with mostly either neighbourhoods seen in only one movie or in dozens (case in point: the distillery), which would lead to really short or long posts. Going by film, you have better consistency and you can follow the narrative of the movie.
I'd suggest watching more movies, but I don't think I could advise anyone to sit through Undercover Brother or Short Circuit 2.
As far as spoofs go, Undercover Brother was pretty good.
I heard this rumor years ago that a film was being made downtown (no idea what part), but they wanted to make it look like a city in the US. In order to do that they tossed a bit of trash around the set area, did some filming then took a break. When they were finished their break all the trash was cleaned up.
@5: I keep hearing that one too. At this point, I think it's morphed into a smug pat-on-the-back story that no longer rings that true.
I've visited four US cities in the past year and they all look pretty good now.
I saw Undercover Brother at The Paramount on Richmond. The biggest laugh it got was when the car chase went past the cinema!
I've heard that exact story about having to throw some litter around to make it look American then it being cleaned up during their break in two places, Toronto and Sydney. Having lived in both cities, as well as in the US, I really doubt it's true. Other cities where Hollywood films a lot, like Prague, probably have the same story.
As gloria said, it smacks of smugness. I can imagine they might want to grunge up an area to make it look more like your typical alleyway when it's not, if they're filming somewhere as hermetically pristine as the Distillery for example.
I thought they filmed parts of The Fly there too (wasn't that where his laboratory/apartment was?) Maybe I'm remembering a different set of old, red brick buildings.
parts of "The Man Who Saved Christmas" were also shot there.
http://www.imdb.com/title/tt0339343/