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

Jake Gyllenhaal and Jessica Chastain Arrive
Roadside Attractions/STX Entertainment

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.


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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.)


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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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  1. MovieBabble says:

    I’m fascinated by what Molly’s Game could bring. The trailer showed off some of that patented Sorkin dialogue and one can’t help but imagine that his film will be wonderful now that he has complete control over writing and directing.

  2. Aaron says:

    I second Allison Janney. She’s received just as much praise as Margot Robbie. She’s the type of film and tv veteran they would be eager to reward with a first Oscar nomination. Emma Thompson has also received excellent reviews for The Children Act.

    What’s exciting is that there hasn’t been a huge dud this festival season – except for The Current War, which was less than rapturously received and will probably sit this season out.

    I, Tonya, Molly’s Game, Stronger, mother!, Three Billboards Outside Ebbing, Missouri, Battle of the Sexes, Lady Bird, The Shape of Water, Darkest Hour, Call Me By Your Name…all these films have wildly passionate fans and all contain highly acclaimed performances. Should be an interesting Oscar season.

    • Kevin says:

      Similar to Idris Elba, most of Allison Janney’s noteworthy work has been on television, so the film academy may be less inclined to view her as overdue than you’d think.

      While festival reception (we can’t really call it critical reception until the actual release) has been quite good for most of those movies, the commercial prospects for each look quite bleak. There is a sense that critics, fearing the future of the industry, could end up going a bit easier than they otherwise would on this fall slate. We should also prepare for another round of diversity controversy, given the demographic makeup of the actors in these pieces. I am not expecting a particularly uplifting awards season this year.

  3. Querbus says:

    I think Richardson would get in over Maslany in Supporting Actress because it’s a scene-chewing turn. Also, BAFTA and the Hollywood Foreign Press absolutely love her, and she’s almost certainly getting a BAFTA nom. It’s been ages since she’s had a plum film role.

  4. Bryan says:

    Is Amazon giving “You Were Never Really Here” a 2017 release? I’d love to see Joaquin in the mix again after the Cannes buzz and a great first trailer.

  5. Tweets also praised Allison Janney a lot for I, Tonya.

  6. Bill B. says:

    Gyllenhaal was robbed of a nomination for Nightcrawler. He was brilliantly creepy.

  7. So there’s a chance Robbie/I, Tonya might move up to 2017? Hmmm….I do hope it’s withheld until 2018 though. This year is too crowded as it is. I’m hoping a few get pushed back so they don’t get buried in the abundance of this awards season.

    I’m thrilled for Chastian and Gyllenhaal both, as well as their films. If Chastain is nominated, I wonder if she can win. I was and still am rooting for Hawkins atm, and think her type of role might just possess that extra factor. But Chastain is considered “due” (not overdue, by any means, but due because they feel she was robbed by J-Law). Meanwhile, Gyllenhaal is DEFINITELY “due” for at least a 2nd nomination. Both of these actors continue to seek challenging, fascinating roles.

    And if proper awards traction can be attained by both, I hope their supporting players may possibly ride the wave. (Even though they merit it on their own.) But if Chastain becomes a frontrunner, I can see Elba getting his first nod. Meanwhile, since supporting actress is…well, practically barren–I can see a slight possibility of a push for Maslany, although I’m skeptical because it’s part-wishful thinking. But her positive reviews are exciting at least.

    • Kevin says:

      Are there any actors you are not hoping get nominated?

    • Steve says:

      My guess is that Elba gets in and Maslany doesn’t, unless her film absolutely explodes. I think people are ready to welcome him that way. As for Jessica, I’d love to see her win. It’s time that happened. But Sally H. may be hard to beat.

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