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Nicole Holofcener attends the The Land of Steady Habits red carpet premiere during the 2018 Toronto International Film Festival on Sept. 12, 2018, a couple days before the film begins streaming on Netflix.Sonia Recchia/Getty Images for Netflix

As she spreads jam on a piece of toast and advises a young woman about marriage (“I didn’t think about it, I just did it”), my first sight of writer-director Nicole Holofcener in the Netflix lounge of Toronto’s Shangri-La Hotel truly feels like a scene in one of her movies. Just put her long-time muse Catherine Keener in a peasant blouse and you’ll have another acclaimed dramedy from the creator of Lovely & Amazing and Walking and Talking.

For fans of a certain type of talky, radically vulnerable and always woman-driven dramedy (think Nancy Meyers with her claws out), Holofcener is the greatest writer-director of her generation. At the Toronto International Film Festival, she has two formidable titles, having co-written Marielle Heller’s Can You Ever Forgive Me? (a biopic based on Lee Israel’s memoir, which should earn the screenwriter an Oscar nomination if justice prevails) and directed her sixth feature, The Land of Steady Habits.

Both films showcase Holofcener’s unique ability to portray the most broken of people and ensure they earn our sympathy. She’s obsessed with the lengths characters will go to not learn the painful lessons that would make their lives so much easier, depicting the most unseemly and self-destructive moments in someone’s life as a badge of honour. She’s also a chameleon, applying her voice to everything from Woody Allen-esque New York family dramas (Please Give) to sardonic ensemble comedies about the privileged class of Los Angeles (Friends with Money) to a truly hopeful, wistful middle-aged romcom (the best movie in the world, Enough Said).

In The Land of Steady Habits, which starts streaming on Netflix on Sept. 14, mere days after its TIFF premiere, Holofcener enters the world of broken men. Australian actor Ben Mendelsohn plays Anders, a wealthy ex-banker who copes with his remorse of being retired and estranged from his wife (Edie Falco) and son (Thomas Mann) by developing a troubling friendship with a teenage drug addict. His regression into casual sex and drug use is straight from Ted Thompson’s 2014 novel (the first time Holofcener has adapted someone’s else work as a director) and is the most unsettling in the filmmaker’s oeuvre.

“Netflix allowed me to make this movie exactly how I wanted to make it and so it felt like a good trade-off,” Holofcener said. “It’s not unlike one of my films, except it goes much darker, sadder and creepier. It’s not like I was looking to write about a male protagonist, I just really liked this one. And then I got to work with Ben Mendelsohn as the lead and that was wonderful.”

While Keener, Holofcener’s cinematic stand-in, is sorely missed here, Mendelsohn is a perfect fit for the filmmaker. The rakish star has never been more attractive, or pathetic, and will make you develop a very weird crush that will flip everything you know about middle-aged men in Patagonia parkas gently inquiring about what antiques they should buy for their new condo, before gaslighting you for being unable to maintain their erection. (It is that kind of film.)

“You’re attracted to [Mendelsohn] because he’s incredibly attractive,” Holofcener said as she assured me. “And that was part of why I cast him, not so much for his handsomeness, but for the softness in his eyes where you can see his humanity, despite his terrible behaviour. And he was so great to direct, he was like putty in my hands."

When asked how Holofcener can travel to such dark, humiliating places in her writing and then instruct other people to act them out in front of her, she says it’s always a process of disassociation.

“There were some tough scenes in this film, but Please Give was the hardest,” she said about her 2010 drama, in which Keener plays a New York antique dealer who develops a guilty conscience about her privilege. “The scene where Catherine volunteers with the Down syndrome kids made me very anxious because she was playing me and she’s falling apart and I can’t fall apart, I’m the director! So it was very, I guess what people call ‘meta.’ Is that what that means when you’re in and out of something at the same time?”

It was now time to ask Holofcener the inevitable question – how it is being a female filmmaker whose 1996 first feature, Walking and Talking, was produced by Harvey Weinstein and whether she feels if things are actually changing. Because what is going to happen now that we’ve talked and shared so much in so many panels and documentaries and TIFF Share Her Journey rallies about the issue? Holofcener rolled her eyes through most of this query.

“Well, percentages are going up, right? That’s the only way to know. But I still open the [Directors Guild of America] magazine and there’s usually one woman amongst maybe 20 men whose movies are screening and they’re mostly white. I’ve been so fortunate so I haven’t been as angry as I should’ve been … but I do always try to help young female filmmakers. I think we need all the help we can get," she said.

“I did this round table recently with these other terrific female directors and we had nothing in common, except you know, our genitals," she added. "They were lovely, but we all kind of looked at each other like: ‘Why aren’t men in here? What is this about?’ It’s ridiculous; I want to be mixed in with other people. Even using this word ‘journey’ sounds so feminine and almost soft. It sounds like I write in my journal.”

The Land of Steady Habits has its final TIFF screening at 9:45 a.m. on Sept. 15 at Scotiabank Theatre and begins streaming on Netflix on Sept. 14.

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