'Molly's Game': How Aaron Sorkin Bet the Farm on Poker-Queen Biopic – and Won

Why the Oscar-winning screenwriter went all in for his directorial debut about underground card-game impresario Molly Bloom

How Oscar-winning screenwriter Aaron Sorkin took a gamble on poken-queen biopic 'Molly's Game' for his directorial debut – and won the whole pot. Credit: Michael Gibson

There are two things you should know about Aaron Sorkin. 

One is that the man likes to talk. A lot. This will not surprise anyone who's seen the 1992 screen version of his play A Few Good Men, starring Tom Cruise and Jack Nicholson. Or has watched a TV show he's had a hand in developing, like the one about an all-sports cable channel (Sports Night) or the one about an all-news cable channel (The Newsroom) or the Emmy-winning one about an all-drama idealistic White House (The West Wing). Or remembers the sharp, rat-a-tat-tat dialogue in the screenplays he's written or cowritten for The Social Network, Moneyball and Steve Jobs. You know that shot in every film about New York summers, where kids are splashing around a gushing fire hydrant? Sorkin is the verbal equivalent of that hydrant. At one point, his publicist has to shuffle him off to his next interview while he's still finishing an answer, which the gentleman is determined to extrapolate on from every conceivable angle. So the 56-year-old writer keeps chatting as we speed-stroll down a hallway – at which point it occurs to everyone concerned that they are taking part in a real-life Aaron Sorkin walk-and-talk scene.

The second thing – the bit that is surprising, given the reason Sorkin is at the Toronto Film Festival, in September of 2017, talking to journalists in hotel passageways – is that the man hates poker. "My TV is permanently tuned to ESPN, so you can't help but trip over the World Series of Poker every so often," he says. "And it is the Worst. Spectator. Sport. Ever. I’ve tried watching a few minutes of it – even while I was writing this movie, which is when it would have been the most useful to me – and it's the exact opposite of 'You can't take your eyes off it.' You can’t keep your eyes ON IT! Because I don't want any of these guys in their Member's Only jackets and bad sunglasses and backwards baseball caps to go home with any money. I'm not rooting for anybody. Is there a way the waitress can win instead?!"

The game, in other words, is not why Sorkin decided to write and – for the first time in his decades-long career, direct – Molly's Game (which opens wide on January 5th), the story of former Olympian hopeful-turned-underground "Poker Queen"-turned-enemy of the state Molly Bloom. As played by Jessica Chastain, this woman isn't much of a motormouth, at least at first. Her skill lies in silently listening and playing very, very close attention to the ins and outs of how her boss's invite-only crème de la crème card game works. Soon, she's running her own high-roller, celebrity-filled poker nights, first in Hollywood and then in Manhattan. The Russian Mob takes an interest. So do the Feds. And then, when it behooves Molly to speak in order to save her skin, she shuts up. 

So yes, he could give a flying fuck about how an ace-high hand fares in a Texas Hold 'Em showdown. But refusing to compromise your principles when the chips are down – now that was something the man admired. And a strong moral center was what Bloom had in spades. "Listen, I love watching superheroes with capes as much as any 12-year-old," Sorkin says. "But integrity, character, doing the right thing ... that's what I love writing about. I basically keep writing characters that are variation of my father. And Molly reminded me a lot of my father."

The man takes a quick breath. "And also if Wile E. Coyote was crossed with Jessica Rabbit." 

Sorkin had actually been contemplating several projects when a lawyer "who I knew socially" passed along his client's book to the screenwriter – a tome blessed with the Sorkin-level verbose Molly's Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World. Despite the fact that the dreaded word poker was listed prominently in the title, he agreed to give it a read and found the book "fun ... but I had zero interest in adapting it. None. Not in the slightest. And then I met Molly, and everything changed." 

Specifically, Sorkin says, it was the disconnect between the story that Bloom's book told and the real version of her tale. "It wasn't just that she had a sly sense of humor and was smarter than I was – one does not have to be too smart to pull off that feat," he notes. "It was the why behind Molly deciding to leave so much out of the book. She didn't feel she could let people down when she'd given them her word, which was something that meant a lot to her. What actually happened was a lot more complicated, nuanced and emotional than what was on the page. 

"Plus when I met her," Sorkin adds, "she'd just been sentenced to 200 hours of community service, had been handed a massive fine and was paying several millions' worth of taxes on the money the government had seized! Yet Molly just seemed very casual about it. After that first meeting, I felt like I knew her well enough to tell her, 'I've never met someone so down on their luck and who seemed so confident.'" He left that face-to-face knew that he wanted to tell her story. What the writer didn't know was that he'd also just unwittingly signed up to become a director as well.

When Sorkin finished the screenplay for Molly's Game, he did what any in-demand Hollywood scribe would do: He gave it to the best filmmaker he knew. "Like anything I write, I had a strong emotional attachment to it and I want the very best director to make to it," he says. "So I went right to David Fincher. I gave it to him first – I mean, I'd give any of my scripts to David first!" According to Sorkin, the Social Network auteur was completely on board to take the reins (ironically, the Oscar-nominated movie about the founding of Facebook was almost Sorkin's directorial debut per a making-of doc) before running into problems regarding the proposed budget and walking away from the table.

"Ok, fine, since it wasn't going to be David, it was going to be somebody else," the writer continues. "But I always had a fear that, because of all the shiny objects – the money, the decadence, the sexuality, the Hollywoodness of it – it was easy to make something where all of those things could overwhelm the story that I wanted to tell." The thought of directing it himself had not occurred to him; it was the movie's producers who initially proposed the idea. "There was a meeting between myself, Mark Gordon and Amy Pascal in which we all had a list of directors in front of us. We went through the pros and cons of each of them, but apparently, there had been a conversation before I had arrived. After the last name was debated, they said, 'Why don't you do it?' This was right before Christmas ... they asked me to take the holiday break and think it over."

"There's a line: 'Mmmmm ... I'm a brat.' We're doing the scene for the first time, I say, 'Mmm ... I was a brat.' And he yells, 'Cut. Jessica, five M's ... not three M's. Five.'
-Jessica Chastain

When the trio met again, Sorkin started to lay out his apprehensions. "And Mark just cut me off and said, 'Look, there's no I'm-leaning-toward this or that here ... you're either in or you're not.' And I just said 'I'm in.' At which point I was struck by an overwhelming sense of terror that I still have yet to shake." He laughs. "Maybe one day."

He began looking in to casting immediately. It was Pascal who suggested Idris Elba for the part of Molly's lawyer – Sorkin had loved a five-episode arc the actor had done on The Office, so he enthusiastically cosigned. He wanted Kevin Costner for the role of Molly's father, but figured "there was no chance in hell" they'd get him; when the Oscar-winner did get onboard, Sorkin gifted him with a showstopper of a monologue, in which the hard-driving dad distills a decade's worth of therapy into 10 minutes. ("With an actor like Kevin and a scene like that, it's sort of like driving a Ferrari," the director says. "You don't have to put your foot on the gas very hard.")

As for the part of Molly, that proved to be a little tougher to fill. "Write down a list of actresses who you think would be up for it," Sorkin says, "and I guarantee you I had a meeting with all of them. All fantastic, too, but the role required someone to play her from age 22 to 35, and I wanted to skew more toward the latter – so really, if we're being honest, it's Jessica Chastain or Emma Stone." When he did finally talk to Chastain over a long afternoon, the connection was immediate. "You could see Molly's sense of humor, Molly's smarts, from the moment she opened her mouth. She just sort of hit out of the park from the first second."

"Yeah, I thought he'd be a total control freak," Chastain says, laughing over the phone several months after the film's Toronto premiere. She's already begun promotional duties as the holidays, and the movie's Christmas release in New York and Los Angeles, approaches rapidly. "This was before I'd met him, mind you! His writing is just so precise, you assume the man would be like, 'I am the only genius on this set.' And then I met him, and he could not have been more collaborative, more open to exploring things, more 'well, what do you think?'"

Which didn't mean, she's quick to add, that Sorkin wasn't occasionally nitpicking actors over what he'd written, sometimes down to the letter – literally. "He loves to tell this story," Chastain says, "about ribbing me over one single line. It was simply, 'Mmmmm ... I was a brat.' And we get on set, Aaron calls action, we're doing the scene for the first time, I say, 'Mmm ... I was a brat.' And he yells, 'Cut. Jessica, five M's...not three M's. Five.'

"But my revenge," she continues, "happened a little later, when we were rehearsing a scene, and I say, 'Yeah.' And he walks over and goes, 'That's not the line, Jessica.' 'Uh, no, that's the line, Aaron.' 'I have never written "Yeah" in any of my scripts!' 'Ok, where's the script supervisor?' She comes over. Opens to the page. Guess what word is staring back at him? That was my favorite day on set." She bursts into raucous laughter. "It was like, don't mess with me, man. You wanted memorized and prepared, you got memorized and prepared. 'You may think you write more heightened language than "Yeah," but you will be wrong!'"

And while Sorkin will freely admit that "every sound that comes out of an actor's mouth ... if it's not there in the script, I don't want to it to happen," he mentions that some of his best moment as a director happened because he was willing to let people go completely off-book. "Keep in mind that this movie is not Rounders – there's no Matt Damon or Ed Norton character," he says. "We do not care who wins. This is all about Molly. But we had six or seven days set aside for shooting just poker scenes, and we wanted to get a lot of inserts: chips being pushed forward, ice clinking into glasses, decks being cut and cards being dealt, all that. We'd hired a lot of real players for the background. And during the last few hours of shooting, I reminded them that, when we first got to set, I was going to cut a check for $2500 to whomever had the most chips when we wrapped.

"Then I told everyone, 'Guys, just play cards. Don't worry about your lines or the cameras,' he says. "I wanted them to have an incentive to really go for it. And it turns out – professional card players do not need an extra incentive to win. They just need to win. The reason racehorses run fast is that they have some kind of instinct that makes them want to run faster than all the other racehorses. These all want to be the best player at whatever table they're sitting at, real or fictional. So not only did we get great stuff, a number of folks went home with huge piles of cash. Those extras were the highest-paid people on set. I think [Michael] Cera left without his house."

So has Sorkin now been bitten by the directing bug? For the first time in a half hour of talking, he stops and thinks for a second or two, or five, or 20. "You know," he says finally, "when I was doing Charlie Wilson's War with Mike Nichols, I remember all of us sitting down for the very first table read. You know, there are a lot of words in that script, a lot of lines; some of the actors look a little worried. And Mike stands up, looks at everyone and says, 'Here's how you do this script: start talking when it's your turn. Don't stop until your turn is over.'" Sorkin sits back. "If I can keep making movies that way, I'll do it. I mean, if it's good enough for Mike Nichols ...."