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Oscars: Jake Gyllenhaal and Jessica Chastain Arrive in Very Different Biopics

Aaron Sorkin’s directorial debut “Molly’s Game” and David Gordon Green’s emotional drama “Stronger” landed at the Toronto Film Festival Friday, providing showcase true-life roles for Jessica Chastain and Jake Gyllenhaal, respectively. The two stars, who are incidentally set to partner on screen together in Stephen Gaghan’s Tom Clancy adaptation “The Division,” could dive headlong into very different lead actor and actress Oscar races this year.

It’s been more than a decade since Gyllenhaal roped in a supporting actor nomination for his performance opposite Heath Ledger in Ang Lee’s “Brokeback Mountain.” In the years since, he stumbled just enough (2010’s “Prince of Persia: The Sands of Time”) to recalibrate and maintain a true heading on roles that excite and challenge him. Indeed, that recalibration has become the actor’s ongoing narrative, as performances in films like “End of Watch,” “Prisoners,” “Enemy,” “Nightcrawler,” “Southpaw” and “Demolition,” among others, reveal a fearless trajectory and a desire to work with compelling artists like Denis Villeneuve and Jean-Marc Vallee.

Already this year Gyllenhaal has appeared in Bong Joon-ho’s “Okja,” delivering an off-the-rails portrayal that sparked quite a divisive reaction — one that seemed to amuse the actor all the more. But he’s on the complete other end of the spectrum in “Stronger,” which tells the true story of Boston marathon bombing survivor Jeff Bauman. Bauman lost both legs in the blast and even assisted in identifying terrorist Tamerlan Tsarnaev for investigators, helping to ensure he and brother Dzhokhar were brought to justice. But the film doesn’t focus on the intense manhunt that proved electrifying fodder for Peter Berg’s “Patriots Day.” Rather, it’s concerned with Bauman’s hard-fought recovery and his emotional journey from aimless townie to responsible adult. Naturally, that allows quite a canvas for Gyllenhaal to work with.

“Molly’s Game,” meanwhile, represents an assured transition for screenwriter Aaron Sorkin to the director’s chair. For Chastain, it provides a ripe opportunity to deliver an impressive range as Molly Bloom, a waitress-turned-poker-maven who ran high stakes poker games for elites in Los Angeles and New York. But the story, for Sorkin (working from Bloom’s memoir), isn’t about a waitress-turned-anything. Rather, it’s about a promising Olympic-grade skier who had her career-cut short thanks to a twig (you’ll get it when you see it) and was fearlessly driven to succeed otherwise — all the way into the grips of an FBI investigation.

The film allows Chastain to play confident, vulnerable, proud, ashamed — the gamut. Center throughout is a sense of integrity that gives the character her enigmatic edge. Bloom is a less damaged version of Chastain’s forthright lobbyist in last year’s “Miss Sloane,” but a more nuanced one all the same. She was peripherally in the Oscar race for that film, but “Molly’s Game” ought to leave a deeper impression, depending on how STX Entertainment plans to negotiate its latest Oscar shot. (Pitches for “Free State of Jones” and “The Edge of Seventeen” ran out of track last year.)

The lead actress race is already bottlenecking, however. The Venice and Telluride film festivals just put Sally Hawkins (“The Shape of Water”), Saoirse Ronan (“Lady Bird”), Emma Stone (“Battle of the Sexes”) and Frances McDormand (“Three Billboards Outside Ebbing, Missouri”) on the board. Judi Dench arrived in “Victoria & Abdul” as well, though a movie that slight won’t likely stick while others are sure to linger (even if she is Dame Judi Dench). There are probably half a dozen legitimate contenders besides, and Margot Robbie is primed to leap into the discussion if “I, Tonya” finds a distributor.

Conversely, a less competitive lead actor race benefits Gyllenhaal’s bid. The only sure-fire nominee to be seen so far is Gary Oldman in “Darkest Hour,” and not to put too fine a point on it, but it may be a race to lose to him. Christian Bale could make it interesting with a “Hostiles” acquisition, and there are a few contenders set to drop in Toronto and New York in the coming weeks like Denzel Washington (“Roman J. Israel, Esq.”), Andrew Garfield (“Breathe”) and Bryan Cranston (“Last Flag Flying”), among others. And don’t forget Daniel Day-Lewis’ well-publicized final film performance (for now). All in all, however, that race just feels a bit more fluid than the lead actress competition.

Green and Sorkin’s movies do have a handful of supporting performances worth mentioning. In “Stronger,” Tatiana Maslany stars as Bauman’s girlfriend Erin Hurley, who helps him pull it together with a healthy dose of tough love. The Emmy-winning “Orphan Black” star actually does quite a lot with the familiar role. Miranda Richardson’s complex rendering of Bauman’s mother, meanwhile, is expert but unfussy. In “Molly’s Game,” Idris Elba gets to chew on most of the film’s Sorkin-esque dialogue as an attorney taking on Bloom’s radioactive case, while Kevin Costner stars as her steel-willed psychiatrist father.

But these are films owned by their leads, platforms that will catapult two of the industry’s top stars into the awards conversation just as the prestige season begins to take shape.


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