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It's not every week that two movies set in Toronto open in Toronto on the same day, but this is one such week. Even less common is the fact that both movies – Denis Villeneuve's Enemy and Bruce McDonald's The Husband – are about men in their 30s undergoing heavy identity crises. Then consider that, in each film, Toronto is an oppressively drab, spiritually oppressive place where the primary distinguishing characteristic is a clogged system of looped expressways, the city ribboned by roads to nowhere. In both movies, the spectacle of looming condo towers is regarded with a shudder, and intimacy as an impossibility. This is weird and compels closer scrutiny.

In Enemy, based on a novel by the late Jose Saramago, Jake Gyllenhaal plays Adam, a joyless history professor whose punishingly dull life gets a shot of existential strangeness when he sees an actor who looks alarmingly like him in the background of a movie scene. Striking out in stalking pursuit of the actor, our hero runs smack into his worst nightmare version of himself.

The Husband is about another lost soul in perpetual driving mode. Just before his wife is to be released from prison on charges of having sex with a minor, Hank (Maxwell McCabe-Lokos) starts tracking the teenager in question, hanging around parking lots, eavesdropping in restaurants and peering through school fences in a desperate attempt to build something from the rubble of an exploded life. Humiliated, emasculated, impulsive and obsessive, Hank has completely lost his sense of who he is and thinks that tracking the boy will provide the answer. It won't, of course: With each trip down the shadowy alley of delusion, Hank drifts further away from the ground zero of self.

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It would come as no surprise if he were to pass Enemy's Adam in one of those alleyways, so similar is their state of disconnection, and so apparently endemic to the city itself.

Certainly the movie version of Toronto (when it's not required to play something other than itself) has always provided a particularly conspicuous setting for fracturing of identity.

Going back to Don Owen's Nobody Waved Good-bye (1964), which chronicled a suburban teenager's migration to downtown Toronto in a doomed attempt to establish independence, and again in Don Shebib's Goin' Down the Road (1970) in which a pair of unemployed Maritimers find only rejection and more unemployment in the city, Toronto has so consistently set characters adrift that it's almost a defining characteristic.

Think of David Cronenberg's three best-known Toronto movies – Videodrome (1983), Dead Ringers (1987) and Crash (1996) – or the films that established Atom Egoyan's reputation (Speaking Parts, 1988; The Adjuster, 1991 and Exotica, 1994), and you see a city of terminal isolation and hard, concrete impersonality. Answering machines abound, people live alone in apartments, sex is dispassionate, stalking is prevalent and insomnia epidemic. And yet again in Toronto-based movies as otherwise disparate as The Silent Partner (1988), A Man in Uniform (1993) and Last Night (1998). In this city, the only community is comprised of loners. No wonder Glenn Gould, agoraphobic and reclusive, felt right at home here.

It might be attributed to Toronto's geographical anonymity – no mountains, a perpetually mutating skyline – or perhaps it's that the city lacks a specific identity. Unlike New York, Chicago, London, Paris, Rome or even Los Angeles, Toronto isn't easily placed in terms of distinguishing landmarks – one reason why it's so often dressed in drag as somewhere else. Then consider the envious civic mindset of Toronto being a "world class" city, and you have a place with no "here" here. You have a city always dreaming it is somewhere, or something, else.

Now think about the visual representation of the city in the two new films. In Enemy, Toronto is canopied by a sky that hovers low and sickly yellow, a veil of urban jaundice beneath which people live in vertical cubbyholes, emerging only long enough to cross sprawling parking lots in which cars wait to merge into the blocked arteries of lurching traffic.

While The Husband opts for a different overhead colour scheme – a dull, metallic, sunless blue-grey – it's just as likely to buckle its protagonist behind the wheel, driving in frustrating pursuit of an elusive destination, and trying to avoid the cold stares of fellow travellers suspended at stop lights. In the movie that merges in my head, Hank looks over and sees Adam staring back at him.

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Were the two to pull over for coffee, they might provide some welcome comfort to each other, a shared experience that could offer a way out of their loneliness. But they'd probably have to drive a long way first. Somewhere far, far from Toronto.

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