Aaron Sorkin and Jessica Chastain on Female Characters and Molly’s Game

Photo: Valerie Macon/AFP/Getty Images

Whether they’re collaborating onscreen or off, Aaron Sorkin and Jessica Chastain are a whole lot of fun together. Onscreen, they’re offering the hit Molly’s Game, which represents Sorkin’s directorial debut after a career writing acclaimed projects like The Social Network, A Few Good Men, and The West Wing. In the fact-based film, Chastain stars as Molly Bloom, who ran exclusive, high-stakes poker games with some of the wealthiest and most famous men in America. She’s savvy, competitive, and a hell of a talker: When Molly butts heads with the straight-arrow lawyer (Idris Elba) hired to represent her, it’s a mano-a-monologue clash of the titans, and Sorkin and Chastain are clearly thrilled to bring this real-life character to the screen.

When Vulture caught up with the two of them at the Toronto Film Festival, their interplay was just as delightful as a scene Sorkin might have scripted. They admire and tease each other, often in the same sentence, and Sorkin and Chastain had a whole lot to say about how the film came together, why this is a female character worth touting, and portrayals of women onscreen. First, though, there was a little small talk, and a clarification Sorkin was keen to solicit: What’s so funny about him going to one of Hollywood’s most notorious nightclubs?

Jessica, I know that you like to go see other movies when you come to film festivals. Did you have the chance to see anything yesterday?
Jessica Chastain: No, I was doing a little X-Men.
Aaron Sorkin: So it’s true?
JC: What’s true? X-Men?
AS: You’re saying you were at the X-Men?
JC: I’m in X-Men, the movie.
AS: That’s what I’m saying. You’re in the X-Men … thing.
JC: I was shooting yesterday.
AS: And you’re a villain?
JC: Well …

Villainy is in the eye of the beholder.
JC: Exactly. Villainy is … actually, I could go there super easily, but let’s not talk politics.
AS: [to Vulture] I have to ask you something quickly before we get started, because I’m so curious. You guys ran a piece a few weeks ago, after I had done a phone interview with someone else …

The post about you going to 1Oak for the first time?
AS: Yes.
JC: [Laughs.]
AS: And I couldn’t figure out why. I understood that this is obviously snarky and that there’s something funny about my having gone to 1Oak, but I could not understand what it was.
JC: I think for me, I would like to imagine what Aaron Sorkin even wears to 1Oak. [She gestures to his tan suit.] Did you wear this?
AS: I don’t even remember what I wore yesterday.
JC: Did you wear black jeans?
AS: I don’t think I own 1Oak clothes.
JC: Do you own a pair of black jeans?
AS: No. I own a pair of blue jeans. A couple pairs.
JC: I think that’s what’s funny about it, Aaron.

It’s a fish-out-of-water story.
JC: It’s amazing. It would be like if I went to the boxing fight, since I’m not really into men beating each other up. It’s that kind of thing, you know?
AS: Hmmm, okay. Well, I’ll tell you what I did discover from that trip, which made it into the movie: There are girls in pink wigs that you buy shots for. They’re employees of the place, but you buy them shots, which obviously uses up all the liquor. I thought it was so funny. I couldn’t get over it, and neither could Molly.
JC: And so you used it in the movie.

Aaron, you’ve always seemed to enjoy plunging yourself into some unfamiliar milieu for your work and learning everything there is to know, from slang to power structures. When I see Molly googling poker terms as she hears people say them at her games, I thought, “I could see Aaron Sorkin doing that, too.”
AS: That’s true. In fact, in this particular case, so many of the questions that Idris Elba’s character Charlie asks her are questions that I asked Molly. He’s so curious about her and obviously there are pieces that are missing, so he keeps asking her these questions that, at first, she doesn’t want to talk about. As a favor to a lawyer, a friend I know socially, I read Molly’s book and agreed to meet with her, and in that first meeting, which was an hour long, and I knew by the end that there was something there that was really wonderful and I wanted to write it. It began with her not being anything like who I thought she was going to be, and Charlie has that surprise, too. This woman is not who the tabloids made her out to be, and that was my discovery.

The movie was a bit of a discovery for me, too. I liked it so much, and I had gone in sort of wary, wondering if Molly’s story could really sustain a film for two hours and 20 minutes.
JC: It’s two hours and 20 minutes?
AS: It’s two hours and 12 minutes.
JC: I didn’t know that! It’s probably a good thing that I couldn’t tell. I’ve been in movies where you could tell that when you watched it.

I know you’ll blanch at this comparison, but it reminded me of Goodfellas in that if I were to come upon this on TV sometime, I’d be powerless not to watch and get swept up in it. It’s fun, and it just moves.
JC: He had me watch Goodfellas!
AS: First of all, I should tell you that no one is going to mind being compared to Goodfellas. But I had her watch Goodfellas just because there’s so much voice-over in it, like there is in Molly’s Game. And to my knowledge, Jessica had not done a film with voice-over at all.
JC: Yes, I have.

She’s done the mother of all voice-over: Terrence Malick voice-over.
AS: Oh, yeah, Tree of Life. Tree of Life.
JC: I had done a couple. And I had seen Goodfellas already, but it was really great for me to see it again because the voice-over in that is very different from any voice-over I had done in the past.
AS: It’s also different than the voice-over in Molly’s Game, and here’s how: Yes, there’s a ton of voice-over in Goodfellas, but it’s largely expository, whereas the voice-over in Molly’s Game … sure, there’s some that’s expository, but a lot of her character and personality is in that voice-over. We’re seeing another Molly in those moments, a Molly who knows how this story ends.
JC: Like a TED talk.
AS: I would put it to Jessica: Pretend you’re doing Molly Bloom’s TED talk, and she’s been asked to tell her story.
JC: My favorite thing is that when we finally finished the voice-over — and actually, I really liked doing them and I’m glad we spent so much time on it — is that I said to Aaron, “Now, as a gift to me, I want you to take the most dramatic scene in the movie and voice Molly for me.” And he did.
AS: Somewhere around here is the footage of me saying, “It’s. My. Name!”
JC: I have the video clip. I took it on my phone.
AS: I’d also like to say something else, which is that before we started shooting, there was a lot of conversation about Jessica’s hair color in the film.

AS: Why, indeed. A) I don’t really care that much, and b) I am incredibly uncomfortable telling anyone, much less a woman, what I want them to look like. “Here’s what would please me, if you looked like this.” I’m very uncomfortable with that, but hair color had a slight importance because I wanted Molly to look different in present day than she does in flashback, and I wanted there to be a couple of different flashback looks as Molly gets further and further from who she was as she’s reinventing herself. I really liked Jessica’s red hair …
JC: … but I wanted to look more like [brunette] Molly, and he wanted to make her look like me.
AS: But who cares if you look like Molly? It doesn’t matter.
JC: This conversation went on for a long time — “red hair, brown hair, red hair, brown hair” — and then, finally, we’re on set and I do look like Molly. And I will say, many people have told me that I looked better in this movie than I ever have before, which is interesting. But anyway, we’re on set, and someone holds up a poker chip and Aaron goes, “Is that poker chip red?”
AS: I said, “You’ve got to understand, I’m color-bl …” I froze. I stopped in the middle of the sentence. And Jessica went, “Were you about to say, I’m color-blind?”
JC: We’ve been talking about my hair color for ages!
AS: Well, it was a good discussion, because it looks great.

Jessica, you were on the jury at Cannes this year and you bemoaned the lack of interesting female protagonists.
JC: Actually, I’ve seen some of the stuff you’ve written about that and I really want to talk to you off the record about it. Come find me later in the festival.

Well, I think those comments struck a chord with people who want to see female characters who aren’t just passive love interests. So now that you’ve got everyone’s attention, how would you sell Molly’s Game to them as being in line with those comments?
JC: It’s the story of a woman who uses her intellect and her competitive nature to become powerful in an industry traditionally dominated by men. For me, that is a very interesting story to tell. It’s also a woman who has her own agency. She’s not there serving the male characters in the story, she has her own wants and desires. She has an arc in the film. A character can be small and have an arc, but this film rests on Molly’s shoulders and we spend a lot of time with her. As you know, I love movies and see everything I can, and I will say that what’s really been heartbreaking to me is that there are these brilliant filmmakers I’ve always wanted to work with, but when I look back over their careers and say, “Have they ever made a movie about a woman?” in many cases, with these great filmmakers, the answer is no. Aaron Sorkin is already a filmmaker in his own right and so successful; he didn’t have to write a movie about a woman’s journey, and he did. That, to me, is so touching and inspiring and I hope other artists in the industry will take note of it. I hope they’ll know that you can tell a story about a woman and it doesn’t have to be this traditional, stereotypical role of what a woman was in the past.

Aaron, you’ve written female co-leads before, but is this your first no-bones-about-it female protagonist?
AS: It is, but I certainly didn’t say to myself, “What I’d like to do now is write about a woman.” Listen, the fact that Molly is a woman is not irrelevant to the story, by any means, but I will say that it’s irrelevant to how I wrote it. I wasn’t thinking in a different way.
JC: You have a daughter. Your daughter is very much important to you.
AS: Here’s what I’m nervous about: I don’t want how I write a character to be interpreted as how that character speaks. One of the things about this that I was really attracted to was Molly’s wit, her brains, her communication skills. Most of the characters I write are smarter than I am, and that appeals to me. Most of the characters that any writer writes are more something than the writer is, right? They’re more daring than the writer is if you’re watching Mission: Impossible, they’re sexier than the writer is if you’re writing a romantic comedy, they’re more villainous than the writer is if you’re writing that sort of thing. So Molly definitely fell into the category of characters who are smarter than I am, but I don’t think there’s a specific way a woman is supposed to speak, and I’m not going to make that statement about three and a half billion people. I was just writing Molly. I wasn’t writing a woman.

Has your daughter influenced your writing at all?
AS: As far as Roxy goes … she’s a teenager now. That happened fast, she used to be very little. Fatherhood is something I’ve started writing about more. Back in Steve Jobs, I was doing it, and it became a very important part of the story [of Molly’s Game] to me. But even more than that, Molly was a person and a character that I ended up wanting my daughter to take a look at and admire. Her integrity, how important capital-C character is to her … I thought that was so important today when it is tougher and tougher to raise a woman. Particularly where I live, which is Los Angeles, but I think it’s everywhere. Young women are being asked to value themselves in terrible ways, so this was yet another reason why this all appealed to me.

Aaron Sorkin and Jessica Chastain Dish on Molly’s Game