Director Jason Reitman doesn’t mind unhinging his audience

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There's a polarizing moment early in the new drama Labor Day, which opened Friday, a moment when you either buy into the story – about an escaped convict (Josh Brolin) who takes refuge in the home of an agoraphobic single mother (Kate Winslet) and her adolescent son (Gattlin Griffith) over a steamy summer weekend in 1987 – or you don't.

I won't tell you what the moment is; you'll know. But when Labor Day premiered at the Toronto International Film Festival last September, I asked its writer/director, Jason Reitman, if resting a whole movie on such a delicate hinge makes him nervous.

He has an answer. Montreal-born, L.A.-raised, the son of director Ivan Reitman, Jason is 36, genial and hyper-articulate. He always has an answer. But, first, he has to stand up in mid-sentence to replace a phone that the previous occupant of this hotel room has left dangling off its receiver. "Sorry … it's been bugging me," he says.

He sits back down. "Okay," he continues, "I feel like I've been dealing with that delicate hinge moment since the beginning of my career. When you decide your hero is going to be the head lobbyist for Big Tobacco," – as Reitman did in his first feature, 2005's Thank You for Smoking, which won an Independent Spirit Award for best screenplay – "you know that some in the audience are not going to go with you. When a pregnant teenage girl has a blasé attitude toward her pregnancy" – as was the case with his second feature, 2007's Juno, which netted him an Academy Award nomination for best director – "or when your hero fires people for a living, and promotes an ideology that life is meant to be lived without connection to other human beings," – that would be 2009's Up in the Air, which earned Reitman three Oscar nominations, for best screenplay, director and picture – "you're going to lose people. I'm drawn to that. That's what gets me excited. That's why I'm here."

That 2011's Young Adult – Reitman's precursor to Labor Day, about an aging mean girl (Charlize Theron) who is not redeemed – was his most polarizing work also makes him most proud of it. "It's probably my most truthful film," he says. "I'm disappointed by how few films challenge me that way. I'd much rather spend time with Mavis [Theron's character] than I would with traditional film heroes who believe in good things, and good things happen to them, and they save the day. To me, that's boring. Give me people who are challenged, who are messed up and troubled and don't understand life, who have chosen their own avenues and have a different point of view. I find that far more interesting."

Reitman's previous pictures have been, to one degree or another, comic dramas. Labor Day is different; it's a love story that flirts with old-fashioned melodrama, both dream-like and tense. It's based on Joyce Maynard's 2009 novel, whose manuscript had been passed over by publishers until Maynard's agent sent it out without her name on it. "Then it got a ton of heat, because everyone thought it was the first work of a young man," Reitman says. "There was a rumour that James Franco had written it. It's amazing that a woman in her 50s nailed the mind of a 13-year-old boy, who narrates the story."

Reitman's producer, Helen Estabrook, found the book for him: Although it was different from anything he'd done, she knew he would love it. "She was 100-per-cent right," he says. "It was about so many themes I'm drawn to: inexplicable love, desire, trust. I love characters who make unexpected decisions, and leave me asking why. This is a book, and hopefully a movie, where three people come together, you don't exactly know why, you're not completely comfortable with it, but there's a part of you that wants to go along with it, and knows they need each other. That they're broken and somehow they're going to heal each other."

Many of Reitman's key crew members, some of whom he's known since he was a teenager, work with him from film to film; for this one, "we knew we had to grow," he says. For weeks, they gathered at Reitman's house to screen dramas and point out details. They watched Body Heat, for example, just to analyze sweat, and spent two hours afterward talking about how sweat looks in hair, how it looks in clothes. Should it be damp? Should it merely sheen?

They also learned, from Maynard, to make pie. A lot of pie. When Maynard's mother was dying, she announced she didn't care about watching her figure any more, and Maynard made her a pie a day. There's a pie-baking scene in the book, and in Reitman's screenplay, he unabashedly describes it as "the greatest pie-making scene in cinema history." Brolin took on that challenge: Over the course of the shoot, in Concord, Mass., he made a pie every day – always the same kind, peach. After he depleted the peach stock in Concord, he had production assistants driving around Massachusetts looking for more.

"Josh is the picture of masculinity, so it was hilarious to show up at the cottage he was renting, and find him wearing an apron, over the moon by the crust he'd achieved that day or the juices he'd coaxed out," Reitman says. "He'd give the pies to the crew, and at first it was really charming, like: 'Oh wow, Josh made me a pie.' By the end of the shoot it was like: 'Not another friggin' pie.'"

It all contributed to the mysterious alchemy of movie-making: Griffith's watchful stillness, the power Brolin brings to a glance, the careful log that Winslet kept of every time her character's hand shakes, every ragged sigh. "You should have seen Kate's screenplay," Reitman says, "notated within an inch of its life, every square of blank space covered with her tiny scrawl." (The omission of Winslet's performance from awards lists is to me the most puzzling aspect of this season.)

"I'm a big believer in chemistry in every definition of the word, in life and in performance," Reitman says. "I can screw up a lot of things, but I have to pick the right actors and they have to have chemistry. It all goes back to a piece of advice my father gave me before I made my first film: 'Your job is not to make things funny or tense. Your job is to find truth on a daily basis.' You have to write a screenplay that you think is funny or tense or dramatic, but once you get to set, the whole job is, 'Does this feel honest?'

"Storytelling in general is a self-discovery masquerading as entertainment," he concludes. "The best stories are bound to address the things that confound us the most."