Reel Toronto: Undercover Brother!
Torontoist has been acquired by Daily Hive Toronto - Your City. Now. Click here to learn more.




Reel Toronto: Undercover Brother!

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.
From downtown to Uxbridge, the Undercover Brother knows how to have fun in the GTA.
Reel Toronto’s crack team of detectives has figured something out. Aside from Chicago and Good Will Hunting, we don’t get too many Oscar-quality productions up here in Hogtown. You would think with so many productions we could average better than, say, Cocktail, but we tend not to do so hot. Still, there’s no shame in providing some laughs, and Undercover Brother does just that.
It takes place in an anonymous, New York-ish city, and after lurking in interior locations for its first half, pulls out all the stops when it tours our town, exterior-style. Look close and you may even spot that rarest of sites: the CN Tower in a film that doesn’t take place here.

It’s always nice to take a spin out on Dundas West.
The film starts (and ends) with a bravura sequence in which the titular Undercover Brother demonstrates his driving prowess. In particular, he manages to parallel park his car after spinning it around several times, all without spilling a drop of his Big Gulp orange soda. He pulled off the stunt out on Dundas Street West, near where St. John’s Road and Laws Street intersect.
Art Deco evil lairs are few and far between.
This is the second Reel Toronto in a row to feature a Dave Chappelle movie, and it is the third in a row to feature the ubiquitous RC Harris Filtration Plant.
In this flick, the Queen East plant plays the island headquarters of the villainous The Man. It’s a nice change from the usual penitentiary roles we’ve seen of late, but we still wonder how such a purty building can be so darned bad.
When Chris Kattan is your bad guy—heck, when he’s in your movie—you’re swimming against the current, baby.
In a nice twist, we actually get to see the interiors this time. If you’ve never toured the luxurious inside, perhaps during Doors Open, you would never guess at all the marble and other design features that lie inside a building with such a straightforward purpose.
Yup, it was even enough to lure James Brown in to bust a move or two and, at the film’s end, it gets blown up. Blown up reeeeeal good.
The irony of our upscale district playing dirty never gets old.
If you read Reel Toronto, you know that every film shot here has to feature the RC Harris plant and/or The Distillery District, and Undercover Brother does not disappoint. This time out, the latter provides the setting for the end of a long motorcycle chase between our hero and the semi-evil Denise Richards. Even in the reverse shots, you can appreciate it in all its red-brick glory.
Bad Girl + Motorcyles + Toronto = Comedy Gold
The chase itself is edited awfully tightly, so it’s hard to spot landmarks, but it clearly zips east along Adelaide Street.
No illusions here. This store actually is a place where rich, white people shop.
When our hero visits the Banana Republic–like “Khaki Republic,” you can clearly spot the Eaton Centre and Pier One Imports out the window. That’s right––we’re on Yonge Street. The store interior is now the Buffalo at 225 Yonge, where white people who want to be cool actually do buy their denim.
It’s a bank office playing a bank office…no big whoop.
When Undercover Brother goes deep, deep undercover as a yuppie-type, he takes in a meeting at a bank tower. We admit we’re not 100% sure, but we know scenes were filmed at Scotiabank and First Canadian Place so…um…take your pic. Either way, that’s definitely the Toronto Islands out the window, with the airport visible on the right.
Again––no irony here. It really is a super-upscale golf club.
The golf course scenes, including the slo-mo golf cart chase, were shot at the lovely (and hoity-toity) Wooden Sticks club up in Uxbridge. Each hole is apparently designed to replicate a famous PGA hole, so if you’re part of the rare Undercover Brother Fan/PGA Fan demographic, this is definitely where you want to tee off.
A team of scientists is working to determine what the name of this facility was when the film was shot.
Hopefully you don’t think we gave James Brown short thrift before. His cameo is part of an elaborate finale that begins outside our very own Sony Centre (aka Hummingbird Centre, née O’Keefe Centre, soon to be part of some kinda crazy L-shaped condominium).
It’s hard to miss the distinctive port cochère, or the Shopsy’s across the street, and the Hockey Hall of Fame lurking in the corner of the frame. It’s impossible to miss the trompe l’oeil on the back of the Flatiron Building as Neil Patrick Harris chases James Brown’s limo down the street.
Other scenes were shot at La Maquette, on King Street, and the 11th Hour club on Pearl Street.
It’s the world’s, um, second-tallest freestanding structure, sucka!
How solid is Undercover Brother‘s Canadian cred? So solid that the production company is called “Three Canadian Brothers.” But did it win even a single Genie Award? As Will Smith would say, “Hell, naw.” What more need be said about the problems with our indigenous film industry?