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With the release of Turning Red and Scarborough, two very different films set in the city, Barry Hertz asks: What image does our ‘world-class’ city offer to audiences at home and abroad?

Illustration by Salini Perera

On the screen, Toronto can be Chicago, New York, Hong Kong, even Kandahar. But in those rare opportunities where Toronto gets to play itself, what image does the “world-class” city offer to audiences at home and abroad? What is, even, a “Toronto movie”?

This month, two new films attempt to answer that question, in wildly different ways. Pixar’s Turning Red casts Toronto as an animated bubblegum-pop paradise, the perfect playground for a young girl discovering herself and her heritage. The micro-budget drama Scarborough, meanwhile, offers a raw street-level view of the city’s forgotten corners. But both are good excuses to list the 20 Best Toronto Movies Ever Made.

Are the following films ranked in order of their excellence? Not exactly. Instead, consider this list a balancing act between genuine cinematic artistry and just how creatively filmmakers depict this strange city of ours. It is all entirely subjective, too, so feel free to yell at me later – though, in true Toronto fashion, please do so in the most passive-aggressive manner possible.

20.5 Kids in the Hall: Brain Candy (1996)

Directed by Kelly Makin

All right, including one extra film is a cheat right off the bat. But I couldn’t not include Brain Candy, even if the comedy doesn’t explicitly take place in Toronto (nor any city, really), and the Kids in the Hall troupe hated making the film, which was as tortured a production as these things could be. Still, the satire of the pharmaceutical industry is filthy enough with images of Sam the Record Man, RBC Tower and Berczy Park to qualify for this list. Plus: Brain Candy is an intensely funny experiment that has only gotten better with age.

Currently unavailable digitally in Canada (which is a scandal!). But if you do some searching on YouTube ...

20. The Stairs (2016)

Directed by Hugh Gibson

I’m unsure that there is a Toronto film as empathetic, as deeply human, as Hugh Gibson’s The Stairs. Shot over the course of five years, the documentary follows three residents of the stigmatized Regent Park neighbourhood – a community outreach worker, a former sex worker, and a drug addict – as they struggle on the road to recovery. Generous and devoid of easy gawking, Gibson’s work is unforgettable.

Streaming on TVO.org

19. I’ve Heard the Mermaids Singing (1987)

Directed by Patricia Rozema

Patricia Rozema’s feature debut remains a marvel of off-beat artistry, 35 years after it became the first English-language Canadian film to win an award at Cannes. Focusing on a temp worker (Sheila McCarthy) prone to flights of fantasy, the dramedy features myriad Toronto hallmarks in fantastical ways, reconfiguring our understanding of the city (especially its skyline). Rozema, McCarthy and co-star Ann-Marie MacDonald would all go on to higher-profile, bigger-budget projects, but I’ve Heard the Mermaids remains a nexus point for Canadian cinema.

Currently unavailable digitally in Canada, though a new 4K restoration will play select theatres starting March 11 (kinomarquee.com)

18. Diamond Tongues (2015)

Directed by Pavan Moondi and Brian Robertson

Like Kazik Radwanski’s films (keep reading), there is a vivid west-end specificity to Pavan Moondi and Brian Robertson’s Diamond Tongues, a cringe comedy that follows an actress (Leah Goldstein) stumbling her way through Toronto’s arts scene. With a sharp script, a courageous performance from Goldstein, and music by Broken Social Scene’s Brendan Canning, Diamond Tongues is a nervy portrait of downtown creatives trying to break through. All this, plus it boasts a genuinely funny George Stroumboulopoulos cameo.

Streaming on CBC Gem; available for rent/purchase on Apple TV, Google Play, Cineplex Store

17. Bollywood/Hollywood (2002)

Directed by Deepa Mehta

Like David Cronenberg and Atom Egoyan, Deepa Mehta has become synonymous with Toronto cinema. Yet the filmmaker has only set a handful of her films here, and each competes with the other for representing that perfect marriage of directorial sensibilities and ineffable Toronto-ness. Which is a long way of saying that, while I still have the opening of 2008′s Heaven on Earth seared into my brain (that unbearably sad journey from Punjab to the suburbs of Brampton), it is Mehta’s Bollywood/Hollywood that has the Toronto-movie edge. Joyous, colourful and unabashedly Toronto, this melting-pot rom-com is a delight.

Streaming on CBC Gem, Crave

16. Owning Mahowny (2003)

Directed by Richard Kwietniowski

The best thing about watching Owning Mahowny – an ‘80s-set drama based on the real tale of a CIBC banker who embezzled $10-million to feed his gambling habit – is marvelling at the towering talents of Philip Seymour Hoffman. The worst thing? Remembering that Hoffman is no longer with us. Somewhere between those extremes is a tense and slick drama that captures Toronto as a neat “just-because” setting: it is used because it is where Brian Molony (”Dan Mahowny” in the film) happened to live, work and steal. Toronto is not so much a character as it is a neutral background player. In that way, Owning Mahowny is one of the more fascinating Toronto movies ever made.

Streaming on Crave

15. Anvil! The Story of Anvil (2008)

Directed by Sacha Gervasi

The best movie ever made about North York (okay, perhaps the only movie made about North York), Sacha Gervasi’s documentary about a forgotten heavy metal band is a head-banging triumph. As Gervasi follows the ups and downs (mostly downs) of guitarist/singer Steve “Lips” Kudlow and drummer Robb Reiner (not that one, even though there are strong This Is Spinal Tap vibes here), Anvil! delivers a true underdog story. One that also acts as a neat chronicle of the city’s Jewish community. Mazel tov, boychiks.

Available for rent/purchase on Apple TV

14. The F Word (2013)

Directed by Michael Dowse

I’m not sure that the world outside of Toronto truly appreciates Michael Dowse’s rom-com. First: its nervous U.S. distributor CBS Films retitled the production What If, undermining Dowse’s ribald-but-sweet vision. Second: I can’t imagine that international audiences get as much of a thrill watching Daniel Radcliffe and Zoe Kazan as they court each other around the city, including an intensely charming moment inside the George Street Diner. Third: Torontonians can sorta boast that we helped make supporting players Adam Driver (pre-Girls/Star Wars/House of Gucci) and Mackenzie Davis (pre-Halt and Catch Fire/Terminator/Station Eleven) superstars.

Streaming on Prime Video, Crave; available for rent/purchase on Apple TV, Google Play, Cineplex Store

13. Take This Waltz (2011)

Directed by Sarah Polley

Ignore the fact that characters jog from Parkdale to Kew Beach. Or that rickshaw drivers can afford to live in non-basement apartment homes (I suppose this might’ve been the case in the early aughts). Instead concentrate on the lovingly sensuous Toronto that Sarah Polley renders, a sweltering antidote to the city’s chilly reputation. Focusing on a love triangle that will make you root for the power of a scalene, Take This Waltz tempts and challenges, all while delivering a summer-set ode to a city written in sweat-stained red ink.

Streaming on CBC Gem, Crave, Hoopla, Tubi; available for rent/purchase on Apple TV, Cineplex Store

12. How Heavy This Hammer (2015)

Directed by Kazik Radwanski

Over the course of just under a decade, Kazik Radwanski has invented a new kind of Toronto film: anxious, intimate portraits of men and women trapped by the impossible largeness of a city that stretches out in every direction. While Radwanski’s 2012 feature debut, Tower, and his 2019 art-house hit, Anne at 13,000 ft., are touchstones, Radwanski’s best Toronto movie is How Heavy This Hammer. The character drama follows Erwin (Erwin Van Cotthem), a depressed father of two who seems almost allergic to the world outside his apartment: a stretch of Bloor Street West that perfectly encapsulates Toronto’s pull toward gentrification and its stubborn resilience to hold onto the dingy, nearly forgotten past.

Available for rent/purchase on Apple TV, Google Play

11. The Silent Partner (1978)

Directed by Daryl Duke

One of the first films made during Canada’s anything-goes tax-shelter era, The Silent Partner is a wild artifact of Toronto sleaze – and proves that the city’s polite reputation is rather phoney. As this list illustrates, filmmakers have long viewed the city as a go-to den of Hitchcockian sin, the kind of place where a psychopath (played by Christopher Plummer) can come in search of easy cash and easier prey (in this case, Elliott Gould’s crooked bank teller, not dissimilar to Hoffman’s antihero in Owning Mahowny). Although screenwriter Curtis Hanson’s adaptation of Anders Bodelson’s 1969 novel is dated and wildly sexist, the film still delivers timelessly cheap and dirty thrills.

Streaming on Kanopy.

10. Turning Red (2022)

Directed by Domee Shi

Animation giant Pixar has set films in San Francisco, London, Tokyo, Sydney and the deepest reaches of outer space. But its most impressive, hyper-local setting might be the Toronto featured in Domee Shi’s Turning Red. From the film’s opening minutes featuring an extremely accurate rendition of a TTC streetcar to its climax set inside the SkyDome (the film takes place in 2002, pre-Rogers Centre), Shi’s tale of a young girl cursed/blessed with the power to turn into a red panda is a giant, juicy love letter to the city she grew up in.

Streaming on Disney+ starting March 11

9. Exotica (1994)

Directed by Atom Egoyan

While 2009′s Chloe is Atom Egoyan’s most Toronto-y film – even with its extremely confused geography – the movie that best highlights the director’s hometown instincts remains the strip-club drama Exotica. A beguiling look at jealousy, loneliness and the city that provides a steady stream of both, Exotica lingers all these decades later, like the scent of a lover you long left (or a lap dance instantly regretted). Curiously, the film’s legacy will likely outlive the last Toronto strip joint, given that an increasingly condo-dense downtown no longer has room in its heart for such venues.

Streaming on Criterion Channel; available for rent/purchase on Apple TV

8. Goin’ Down the Road (1973)

Directed by Don Shebib

Perhaps the first true “Toronto movie” (well, no, scratch that – the real answer might be Don Owen’s landmark 1964 drama Nobody Waved Good-bye, which is unofficially No. 21 on this list), Don Shebib’s Goin’ Down the Road is a hugely influential work that is intoxicating, challenging and deeply sad. So: a stew of vibes that pretty much nails the city. Following two Cape Breton fellas (Doug McGrath and Paul Bradley) who come to the Big Smoke to make it big, Shebib’s film is a scrappy work of cinéma vérité, a poignant debunker of the rural-to-urban dream, and a historical document of a city remaking itself in real-time. Plus, the movie spawned SCTV’s best-ever sketch, Garth & Gord & Fiona & Alice.

Currently unavailable digitally in Canada (well, now I’m just mad ... Although again, there is YouTube ... )

7. Rude (1995)

Directed by Clement Virgo

This year, filmmaker Clement Virgo is set to deliver one of the most anticipated Toronto-set movies in ages: Brother, an adaptation of David Chariandy’s award-winning novel set in Scarborough circa 1991. It is a time-travel project of sorts for Virgo, whose own breakthrough came at about the same time with Rude, a landmark look at Black-Canadian lives. Telling three interconnected stories in Regent Park, where Virgo himself grew up, Rude tackles racism, homophobia and generational trauma with a bold, live-wire energy.

Currently unavailable digitally in Canada (though Virgo says some good news may be coming in the next few months ...)

6. Enemy (2013)

Directed by Denis Villeneuve

If Toronto is a city of neighbourhoods, then Enemy’s Toronto is a city of cerebral freak-outs. Featuring doppelgangers, giant spiders and women performing acts of crush-fetishism (look it up), Denis Villeneuve’s film, released after (but shot just before) his Hollywood debut Prisoners, offers a broken-puzzle Toronto that takes multiple viewings to piece together. This might also be the only Toronto movie to crisscross the city with such devoted detail: Jake Gyllenhaal’s history professor lives in St. James Town, commutes to the University of Toronto’s Scarborough campus (here called the University of Greater Toronto), and makes pilgrimages to Mississauga’s curvy “Marilyn” condo towers. Villeneuve’s Toronto is a deeply creepy place to visit, but I sure wouldn’t want to live there. Which is as best a summation on the city’s evolving state that I can come up with.

Streaming on Crave, Hoopla; available for rent/purchase on Apple TV, Google Play, YouTube

5. Scott Pilgrim vs. the World (2010)

Directed by Edgar Wright

A Toronto epic for the Super Nintendo generation, Edgar Wright’s hyperactive adaptation of Bryan Lee O’Malley’s graphic novel series about a slacker’s up-and-down romance was released in 2010 to a torrent of local hype ... and then underperformed at the box office, dashing the dawn of a new Hollywood-Toronto love affair. But time has been kind to Scott Pilgrim, and given the film’s core elements – O’Malley’s unfettered obsession with Toronto ephemera, a presciently cast group of performers (Canadians Michael Cera, Alison Pill and Ellen Wong, plus pre-Marvel stars Brie Larson and Chris Evans) – there was little doubt it would be guaranteed cult-canon certification. Wright delivers a Toronto that is bright, romantic, and, most challenging of all, fun.

Streaming on Crave; available for rent/purchase on Apple TV, Google Play

4. Videodrome (1983)

Directed by David Cronenberg

I wrestled long and hard, Eastern Promises-style, with whether to put David Cronenberg’s Videodrome ahead of Crash or vice versa. The deciding factor: The great in-joke about Videodrome – that CIVIC-TV president Max Renn (James Woods) is a nasty riff on Citytv maestro Moses Znaimer, who cameos here – might be lost on today’s cord-cutting audience. Meanwhile, Crash’s spin on the city’s roadways will stand long after the concrete falls. Still, Videodrome’s heart pumps Toronto blood through and through, with Cronenberg crafting a horrific satire that speaks as much to our collective lust for on-screen violence as it does to Toronto’s hunger to become something bigger, stronger, all-consuming. Long live the new Toronto flesh.

Streaming on Crave; available for rent/purchase on Apple TV, Cineplex Store

3. Scarborough (2022)

Directed by Shasha Nakhai and Rich Williamson

So many “Toronto movies” capture the quote-unquote quintessential city: attractions instead of communities, destinations instead of homes. Scarborough is blessedly different, offering an intimate view of the Kingston-Galloway neighbourhood, where three children and their caregivers struggle to make it to the next day. Together with screenwriter Catherine Hernandez, who adapts her own novel, filmmakers Shasha Nakhai and Rich Williamson deliver a heartbreaking, wrenching and devastating work that is also, ultimately, uplifting – a true Toronto story.

Now playing in select Canadian theatres

2. Crash (1996)

Directed by David Cronenberg

The greatest argument for the preservation of the Gardiner Expressway, David Cronenberg’s masterpiece – not that other, Oscar-crowned Crash – underlines a Toronto that is crassly seductive and classily dirty, and continues a long dialogue that the director has been having with the metropolis since the start of his career. Shifting the setting of J.G. Ballard’s 1973 novel about the erotic pull of vehicular destruction from London to Toronto, Cronenberg creates a film that confronts and then upends perversions, along with expectations of what exactly a Toronto movie might be. (There are no CN Tower shots, the focus is instead on the city’s labyrinthine highways and the anodyne balconies that look out over them.) It is half polite, half frustrated, fully Toronto. A singular work whose improbability and influence grow with each passing year already, the film will long stand as the most audacious Toronto movie ever made.

Streaming on Crave; available for rent/purchase on Apple TV, Google Play, Cineplex Store

1. Last Night (1998)

Directed by Don McKellar

When the very last movie theatre in Toronto closes its doors (hopefully not in my lifetime), the final screening can only be Last Night. Don McKellar’s end-of-days dramedy is an ode to this wonderful, maddening, beautiful, messy city as well as a break-glass-in-case-of-emergency eulogy for a place, people and style of filmmaking that will one day feel quaint and bygone, if it is felt at all. Set on the eve of the apocalypse, Last Night follows a handful of lost souls (McKellar’s sad sack forced into a final family dinner, Sandra Oh’s stranded wife in search of one last bottle of wine, Callum Keith Rennie’s hedonist crossing off a bucket list of sexual adventures) as they navigate The End as only self-conscious Torontonians can. If this is the way that the city ends, then it is not with a whimper, but a cinematic bang.

Streaming on CBC Gem, Prime Video, Crave; available for rent/purchase on Apple TV

Stories they tell: Directors on their own private Toronto

Michael Ori

Shasha Nakhai on Scarborough

Early in the drama, neglected child Laura is abandoned in the Warden subway station, then rescued by a kindly shopkeeper who offers her a beef patty.

“Warden was our very first day of shooting, and there were just five of us on the subway platform. We couldn’t afford to close it all day and fill it with 200 extras, so we had a small group chasing people to sign release forms if they wandered into the shot,” says Nakhai. “There were no tripods, no lighting, it was bare bones. The Warden station patties are famous, too. They have their own Instagram account! It was important to actually shoot there.”

Tijana Martin/The Globe and Mail

Kazik Radwanski on How Heavy This Hammer

At one point in the character drama, newly separated father Irwin takes his two young sons to the rooftop of his apartment to sadly showcase his exceedingly modest Bloor West hood: “You can see everything from here! Coffee Time! Ali Baba’s!” Turns out the rooftop was the same one above Radwanski’s own apartment.

“It’s this funny relationship with the city: the splendour of it, but also this self-effacing humour,” says the director. “There is a specificity to Toronto that often gets glossed over in other films. It’s about finding the alienation there, or the drama within something quotidian or ordinary.”

Vivien Killilea/Getty Images for SCAD

Clement Virgo on Rude

Rude opens with a hypnotic scene of an Indigenous man (a young Michael Greyeyes) dancing, the downtown skyline in the background – a stage-setting juxtaposition of the natural and urban worlds.

“We shot on top of the old CBC building off of Shuter Street. I don’t know why I had this image in my head as a 25-year-old writing the script, but I always loved the idea of the natural and magical merging together in one image,” recalls Virgo.

“I think I worked Michael too hard in terms of the dancing, though. He put everything into the first take, and I loved it. But as a young filmmaker, I wasn’t sure I had it in the can, so I wanted to go again and again. But he was game, a truly dedicated artist.”

MARTA IWANEK/The Canadian Press

Deepa Mehta on Bollywood/Hollywood

Halfway through Bollywood/Hollywood, the film’s culturally mismatched (or so they seem) romantic leads engage in a Bollywood-inspired dance number atop a downtown building, with Toronto’s skyline behind them.

“We shot that on Wellington Street, the camera swirling around, the view of the lakefront in the back. It was great fun, because I wanted something light, something Canadian, but also about India,” says Mehta. “I had just got shut down with making Water in India, so I came back to Canada and said to myself that the next film needs to be fun. And it was a breeze! It showed Canadian-Indians in a great light, and broke every preconception. That was important to me.”

The best stealth Toronto movies

Aaron Johnson (as Kick-Ass) and Chloe Moretz (as Hit Girl) star in KICK-ASS.Courtesy of Marv Films / Lionsgate

When I think of “Toronto movies,” my mind instantly goes to the late Bob Saget’s forever-underrated Norm Macdonald vehicle Dirty Work, a film that is incredibly Toronto-y but is definitely not set in Toronto.

Other stealth/secret-ish examples: American Psycho (whose filming here caused no shortage of uproar at the time), Mean Girls, Good Will Hunting, Zack Snyder’s Dawn of the Dead, and Resident Evil: Apocalypse (notable for its climax in which Milla Jovovich runs down the side of City Hall’s west tower).

There is also Kick-Ass, which is mostly annoying but retains a place in my heart due to one scene showcasing the Scotiabank Cineplex, which I watched ... while seated inside the Scotiabank Cineplex.

The worst Toronto movies ever made

The cast of The Love Guru.Photography by: George Kraychyk

Don’t think Canadian politeness will let you off the hook, filmmakers. For every Toronto masterpiece, there is a GTA-sized mess: Little Italy (more distasteful than dumpster-diving outside a Pizza Pizza), The Love Guru (in which Mike Myers ruins hockey), Run This Town (which robs Torontonians of the proper Rob Ford story that they so richly deserve), and The Sentinel (ultra-bland political conspiracy nonsense) all come to mind.

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