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Brothers Dave Franco, left, and James Franco in The Disaster Artist.

When he was 14, Greg Sestero was unceremoniously axed from the Monte Vista High School freshman baseball squad. Crestfallen but undaunted, he appealed to the coaches. After all, he was a pitcher, and they hadn't even seen him pitch. What did he have to lose? The coaches – Steve McCatty and Wayne Gross, both formerly of the Oakland Athletics, incidentally – consented, allowing Sestero to step up to the mound.

It all unfolded like a movie. Exterior: a ballpark in the wealthy, Republican suburb of Danville, Calif., empty save for an aspiring youngster and his disbelieving coaches. A gentle breeze blows across the field as the sun sets behind centre field, casting a golden hour glare on the fateful proceedings. Cue Vangelis's triumphant score from Chariots of Fire – or that Eminem rap about nervous vomiting from 8 Mile.

"I went up to the mound," Sestero recalls, decades later. "I threw three pitches, and one of the coaches said, 'I'll see you tomorrow.' I ended up winning the MVP award that year for pitching."

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There's a lesson there, sappy and saccharine as it may be: Persistence pays off. There's no such thing as a done deal. In a way, it's been the wonky arc of the now-39-year-old Sestero's life and career. As the star of the 2003 cult film The Room – famously hailed as "the Citizen Kane of bad movies" – Sestero has spent more than a decade trying to reverse his fortunes on similar terms.

The Room found an audience among underground cinephiles, L.A. comedians and others amused (or perplexed) by its seeming improbability. At the centre of it all, the font from which all of the film's weirdness flows, is writer-director-producer-star-enigma Tommy Wiseau, a singularly odd-looking man whose raven mane falls over his craggy, clay-like face, who speaks in an unclassifiable, vaguely Eastern European, vaguely French accent and who stumbles and sputters through line readings despite the fact he wrote the lines himself. The Room became a midnight movie sensation, with regular screenings in repertory houses across North America throughout the 2000s. Wiseau became a cult-cinema mystery man, an inscrutable Ed Wood, about whom little was known and much was conjectured – he had far-flung Mob ties, he was a high-minded conceptual-art prankster, he was actually a vampire, et cetera.

Sestero, who co-starred in The Room as Wiseau's cuckolding bosom buddy Mark, was caught in the crossfire. Gaining renown for starring in The Room is sort of like becoming famous for winning a hot dog eating contest. It stirred a weird blend of emotions, as Sestero was at once eager to embrace the film's unlikely success while remaining slightly embarrassed about its source.

"It's something I stumbled into," he explains over the phone from Los Angeles. "And it all of a sudden became this thing that people would see. I didn't really have a voice. I never got a shot to develop myself, in a way. Like I can't take The Room and show it to an agent and say, 'Hey man, cast me in something.' It's an alien film."

This desire to regain control of his wildly careening movie career led to The Disaster Artist, an award-winning 2013 memoir that Sestero co-authored with Tom Bissell. The book tells the story of a young Hollywood naif who happens across Wiseau in an acting class. The two form a cagey relationship with shades of The Talented Mr. Ripley and Sunset Boulevard. Jealous of Sestero's talent and youthful, soap-star good looks, Wiseau channels his seemingly endless financial resources into his own ill-fated vanity project.

The Disaster Artist contained much of the melodrama of The Room – envy! mystery! cartoonish theatricality! – but put it across gracefully, turning a movie with grandiose classical Hollywood ambitions into a meta-narrative that actually realized those ambitions. As Sestero says, "My goal was to write something as powerful and affectionate in a way that The Room wanted to be."

Now, The Disaster Artist is a movie of its own, directed by and starring James Franco as Wiseau and younger brother Dave Franco as Sestero. It's the latest improbability and meta-twist in a story that's full of them: a bad movie embraced as a so-bad-it's-good cult movie reworked as a making-of that aspires to be a good movie. The Disaster Artist is set to make its world premiere at TIFF on Sept. 11 as part of the Midnight Madness program. After an early preview screening at Austin's South by Southwest festival in March, it's already drumming up standing ovations and Oscar buzz for Franco's performance as the tortured Wiseau – although such hype should be tempered in light of the dense layers of irony that have come to define Room fandom.

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"I've always had a complicated relationship with The Room," says Peter Kuplowsky, TIFF's newly appointed Midnight Madness programmer. "At some of the screenings of The Room, the laughter felt a little mean-spirited or cynical." He bristles at The Room – or any movie, even the most godawful – being hailed as "so bad it's good." He prefers more charitable terms such as "outsider art" or "eccentric cinema."

A veteran of such outsider/eccentric/don't-call-them-bad-movies cult movie circles (he co-presents regular screenings of such fare at Toronto's Royal Cinema alongside filmmaker/podcaster Justin Decloux under the Laser Blast Film Society moniker), Kuplowsky regards these films as legitimately compelling curiosities. For all their conventional failings on the levels of style or storytelling, they're often shot through with flashes of bungled brilliance, abounding with the intense personalities and preoccupations of their makers.

"I try to join the wavelength of the filmmaker," Kuplowsky explains, "as hard as that may be. That's the fun of the experience: wrapping your head around why decisions were made. It creates a meta-narrative. You're watching a movie and imagining its construction at the same time. A movie like The Disaster Artist illuminated that construction."

With a cast that includes current comedy heavies – alongside Franco are Seth Rogen, Paul Scheer, Hannibal Buress, Jason Mantzoukas and Nathan Fielder – one might reasonably fear that The Disaster Artist indulges the kind of mocking, half-contemptuous laughter that has come to define screenings of The Room. But, like Sestero's memoir, its aim is illuminating, Kuplowsky says. It invites viewers to get on the weird Franco-Wiseau wavelength, sucking them deep behind the scenes of the greatest worst movie ever made. Both Kuplowsky and Sestero compare it to Ed Wood, Tim Burton's deeply affecting (and funny) biopic, which cast Johnny Depp as one of American cinema's most eccentric outsiders.

The Disaster Artist is a fitting reversal of fortunes for Sestero. For him, the movie is the culmination of his 15-year journey inside The Room and the unlikely realization of his 20-something Hollywood fantasies. "The only reason I came to L.A. in the first place was to tell stories and make movies," he says. "Whatever way you can do that – if you can do that – at whatever level, that's rewarding."

With respect to Eminem, maybe you get more than one shot. Maybe you get two or three. And then, even if you bungle those, maybe you can recast that bungling as an affecting story of unlikely, ass-backward success. And then get that story turned into a James Franco movie. Stranger things have happened. And anyone who says otherwise probably hasn't seen The Room.

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The Disaster Artist plays TIFF on Sept. 11 and 12.

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