Sundowners, the new dark comedy from Toronto filmmaker Pavan Moondi, centres on a luckless wedding videographer and his worker-bee buddy who head to Mexico in the hopes of turning their sad-sack lives around. At its core, the film is about the terrifying gulf of expectations that exists between what our lives promise and what they actually deliver. It is occasionally brilliant, if completely uncomfortable.

But its cynical preoccupation with the distance between hope and reality is understandable. Despite this being Moondi's third feature after two widely acclaimed projects (2015's Diamond Tongues, 2014's Everyday is Like Sunday), a solid reputation in an absurdly small industry, and a daring and fresh voice that's the perfect antidote to decades of Cancon gripes, it is a minor miracle that Sundowners got made at all.

"This was very difficult, and took a lot longer than Diamond Tongues, which itself was incredibly difficult to get made," says Moondi, 31, sitting in a quiet west-end Toronto bar one morning last month. "I think we only got Telefilm money here because something else fell through. But it was pretty necessary."

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Indeed, because while Sundowners only cost about $1.2-million to make – peanuts when it comes to American indie comedies or the literal peanut budget on any mainstream studio movie – it is by far the most expensive project of Moondi's career, and likely represents a ceiling for certain Canadian filmmakers not named Egoyan, Cronenberg or Gross (and even those talents face their share of obstacles).

"I started writing Sundowners right after Everyday Is Like Sunday, so it was supposed to be the next one," Moondi says of the script, loosely based on his early years as a directionless wedding videographer, which he used as an admittedly depressing substitute for film school. "The response was that it was too large scale a film, which is fair because it needed to be shot partially overseas, in this tropical-resort setting. So I got a producer who said, 'Write a smaller film, I'll kick in the cash,' and when Diamond Tongues did better than any of us expected, we got the Telefilm money for Sundowners."

Although Sundowners is ambitious in scale when compared with, say, Diamond Tongues, which cost $30,000 to shoot – half of the new film was shot in Colombia, subbing for Mexico, and Moondi snagged a genuine American talent in co-star Tim Heidecker, a giant of the alt-comedy scene – it doesn't seem like it should be that hard a sell for savvy Canadian producers or the various funding agencies that keep homegrown artists afloat. Most importantly, it is crafted with a bracing vision and raw honesty, qualities that stand in stark contrast to whatever definition the public typically conjures when thinking about "Canadian film."

From a distance, Sundowners seems like a rote meshing of two overplayed genres: the vacation-goes-wrong film, and the bros-will-be-bros movie. Yet as Eeyore-like videographer Alex (stand-up comedian Phil Hanley) and his reluctant companion Justin (musician/actor Luke Lalonde) get dragged to a destination wedding by the former's insane boss (Heidecker), the narrative quickly reveals a darker, more subversive edge.

"I'd been shooting weddings myself and hating it, and I ended up going on this trip to Mexico on which this is loosely based. For a while, it was just my best, crazy story that I could pull out at parties. But when I wrote it as a script, I knew something was missing," Moondi says. "It took a while to realize that I needed to go deeper with the characters, with the real intention to engage with the expectations of what a vacation-gone-awry comedy is. We do it on purpose 10, 12 times in the film, where we veer people down a path of where they think they know what's going to happen, but then it doesn't pay off, deliberately."

So Moondi and his team flirt with studio-safe disaster, only to flip the script again and again.

"The risk is that you could disappoint people who want some crazy Hangover type of thing, but it's also about reality getting in the way," Moondi says, freely admitting that his vision immediately extinguished some of the more standard routes of financing. "The Harold Greenberg Fund rejected us because there's no payoff. They wanted bigger set pieces, and that's deliberately the movie I don't want to make. I kept referring back to that Harold Greenberg application because it's the rare grant where they write you pages of analysis of why you were rejected. It was motivational to read it back all the time."

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Yet if Sundowners is considered both not ambitious enough (by the funds set up to help burgeoning Canadian talent) or too ambitious (by private investors), then how exactly is a young filmmaker supposed to reach that next level? Moondi is working every angle he can, going beyond film to make inroads in the still-cutthroat and insular Canadian television market (he directed all eight episodes of CBC's sitcom Four in the Morning, and is currently on the writing staff of the network's Schitt's Creek). But he also half-jokes about signing up for medical experiments to keep his artistic career afloat and admits that the answer to his dilemma is a familiar one.

"I was lucky enough to get Telefilm money on this one, but I feel I should probably try to make a film without it, so I'm not in this self-perpetuating cycle of constantly relying on the Telefilm model. So I have another feature that I'm done writing, and it's the hands of a producer in L.A., where we're trying to cast it and get private money," he says.

"We've painted ourselves into a corner now," he adds. "When you're a Canadian film, you're only eligible for certain programs at film festivals, like 'world cinema.' But the style of films that I'm making are too comedic, and those comedies don't typically find a home in those world cinema programs, because they're mostly foreign language or way more art house than what I'm doing. To get the most of the next one and get it seen by as many people as possible, it just might make sense to make it American with private money."

The flight south carries a certain level of irony, notes Moondi, given that the new film takes place in Montreal and he aims to shoot it there, with an all-Canadian crew. "If you're a Canadian comedy, it is simply hard to brand out of Canada," he says.

That line of reasoning is easily echoed in the work of Moondi's contemporaries, including Matt Johnson, whose raucous 2016 mockumentary Operation Avalanche was acquired by U.S. giant Lionsgate. Which means that unless the industry wakes up to the enormous talent knocking down its door, ready to move on from the micro-budget programs that ensure only a certain level of exposure, Canadian comedies will continue to hit a wall.

Toward the end of Sundowners, its heroes (or, more accurately, its lead characters, as Alex and Justin never quite hit the necessary levels of courage or conviction to qualify as protagonists) head back from Mexico with an air of defeat. But Moondi allows them something of a silver lining, albeit in the subtlest of ways.

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If the Canadian industry wants to champion and develop its own artists rather than propel them southbound, perhaps producers and bureaucrats and anyone with their hand on the till can echo Sundowners ' good graces, and give the country's talent the happy ending they, too, deserve.

Sundowners opens Aug. 25 at the TIFF Bell Lightbox (tiff.net)