Best Actress Watch: Will Jessica Chastain Be a Player for Molly’s Game?

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Jessica Chastain in Molly’s Game. Photo: Michael Gibson/STX Productions/TIFF

This year’s Best Actress race is stacked with laureled veterans and exciting newcomers, and it promises to be a real contest. Many of the leading-lady contenders will be appearing at this week’s Toronto Film Festival, and Vulture is on the ground in Canada to help you sort through their Oscar odds. Which of these talented women will make the final five?

The Actress: Jessica Chastain, 40.

The Awards History: Chastain was nominated for back-to-back Oscars for her roles in The Help and Zero Dark Thirty. For the latter, she won a Golden Globe, and she’s been nominated for that particular award four times.

The Role: Reader, let me be the first to tell you: Aaron Sorkin’s directorial debut Molly’s Game, a biopic about high-stakes poker facilitator Molly Bloom, is one of the most ruthlessly entertaining films of the fall. Perhaps I shouldn’t have been so surprised! After all, Sorkin is an Oscar-winning writer who’s put his fingerprints on some of the best-received films and TV shows of recent vintage, and Chastain has a role here that’s right in her wheelhouse. Bloom is a whip-smart, driven heroine with an unlikely arc: After a freak accident torpedoes her career as an Olympic skier, Bloom moves out to Los Angeles to do Hollywood-underling coffee runs and somehow parlays that into a job running the most exclusive, celebrity-courting poker games in the country. How she gets to that point — and what happens after, when her personal stakes grow even greater than the millions regularly exchanged in all those poker hands — is half the fun.

Still, no matter how laureled Sorkin and Chastain are, you never know what to expect from a directorial debut, and the recent trailer for Molly’s Game didn’t make a whole lot of noise. Tonight’s Toronto Film Festival premiere of the film ought to turn heads, then, confirming Sorkin and Chastain as the sort of pair you’d be unwise to bet against.

Few actresses this year will shoulder more of their movie than Chastain does in Molly’s Game. She’s in every single scene and nearly every single shot; and between her dense, defiant Sorkin monologues and all that snappy narration, she delivers enough dialogue to power two whole movies with a little bit left over. You can easily find a through line from Chastain’s determined Zero Dark Thirty character Maya to the driven Molly Bloom, but Chastain has the space here to show many different sides of Molly, and she’s clearly having a blast playing her. Berated by men who seek to control her, Molly is always working the angles, looking for a way to smoothly turn the tables and give those limited dudes what they think they want while claiming a smarter, more unexpected victory for herself. The movie is long — around two hours and 13 minutes — but moves so fast that every time Chastain’s Molly had to figure her way out of another jam and get one over on the guys, all I wanted was more.

In Her Favor: The leading actors in the last three films that Aaron Sorkin scripted — The Social Network, Moneyball, and Steve Jobs — were all nominated for an Oscar, which bodes well for Chastain’s chances. (Most of those Sorkin films also scored a supporting nod, and Idris Elba, who gets some great late-movie scenes as Chastain’s straight-and-narrow lawyer, will certainly be in the mix.) Since her back-to-back nominations, Chastain has come awfully close to another nod several times, and the Academy may think it’s time to finally give her that third shot.

Working Against Her: Though there are some top-flight awards publicists working on the film, it’s being distributed by STX, a studio that has recently suffered through some big bombs including Valerian, The Circle, and The Space Between Us. (And that’s this year alone!) Will there be enough money left to push Molly’s Game into awards contention, and can its complicated premise — hardly an easy one-sentence sell — entice mainstream moviegoers and build some sort of momentum? Sorkin’s last film, Steve Jobs, was considered to be a major Oscar front-runner until it stumbled at the box office; and while Michael Fassbender and Kate Winslet were still nominated, it wasn’t the bounty Universal had been expecting. I want the best for Molly’s Game, but any poker player knows you can hold a great hand and still run into trouble. Let’s see how the film fares upon release this November.

Will Jessica Chastain Be an Oscar Player for Molly’s Game?