High Stakes: Aaron Sorkin directs Jessica Chastain as a formidable poker queen in 'Molly’s Game'

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It's a highly potent combination: the Oscar-winning screenwriter Aaron Sorkin directing his first movie and the twice Oscar-nominated actress Jessica Chastain starring in it.

The result is STX Entertainment’s Molly's Game, based on the true story of Molly Bloom, a charismatic young Olympic-hopeful skier who, after a devastating injury, took a job running the world's most exclusive high-stakes underground poker game, where the players included Hollywood royalty, sports stars and business titans.

Its path to the screen started with a book written by Bloom, whose winning streak had come to a grinding halt when she become entangled with Russian mobsters and was arrested by the FBI.

Sorkin was initially reluctant to meet Molly, nicknamed “the Poker Princess” by the tabloids, and did so solely as a favor to an entertainment lawyer he knew. "I was not expecting to be impressed. I thought I was going to be meeting a woman who was cashing in on her decade-long brush with celebrity and that’s not something I like," he recalls during a conversation in a beachfront hotel in Santa Monica. Calif. "I don’t like gossip, I think it’s bad for all of us. And I certainly don’t like gossip for money. So I went to this meeting as a courtesy."

But ten minutes into their first meeting, which would be followed by many others, Sorkin knew he wanted to write her story and include many of the facts she had omitted from the book. "Boy, did I want to write it" he says. "This was like a blind date that you are not looking forward to, but you leave knowing that this is going to be the person you are going to spend the rest of your life with. Obviously I am not talking about Molly the person, but Molly the story. It was love at first sight and that had only happened once before, when I was having lunch with Stacey Snider, who was then head of DreamWorks, and she asked me if I'd heard about two guys claiming that Mark Zuckerberg didn’t invent Facebook and that it was them. An hour after that, my agents made a deal for me to write The Social Network."

Sorkin, who won an Oscar for writing The Social Network and is a five-time Emmy winner for the TV series “The West Wing,” has a distinctive and unmistakable style, although not everyone is a fan of his witty, fast-talking dialogue and morality tales with politically liberal messages. Still, “The West Wing” is considered by many to be one of the best television dramas of all time.

To the Hollywood powers-that-be, he is a bona-fide moneymaker, with hit movies going back to 1991’s A Few Good Men (based on his stage play). He followed it with Malice and The American President and created the highly praised half-hour series “Sports Night” and the short-lived drama “Studio 60 on the Sunset Strip.” Following his adaptation of Charlie Wilson's War, he wrote The Social Network and received more acclaim for Moneyball and Steve Jobs, although his HBO cable drama “The Newsroom” received more mixed reviews.

Reading Bloom's book, Sorkin was worried about the implications, because he had worked with some of the people she had written about, including four very famous actors. Some were his friends.

He spent the next two years hearing more of her stories and another year writing the screenplay. "I started out the same way I have always started out, though, with quite a bit more enthusiasm," he recalls. "There was something here that was very special: I felt that where other people were seeing a story of glamour and decadence and sex and money and bold-faced Hollywood names, I was seeing a story set against the backdrop of those things but I was also seeing the story of an honest-to-God, real-life movie heroine—someone with a kind of quiet integrity and character that is rare today, even less common in popular culture. I just felt that I had found a hero in the strangest place and that even Molly herself didn’t realize that."

To avoid using the real-life names in the drama, he invented a composite character, played by Michael Cera, to replace the high-profile movie stars who were Molly's regular clients and came up with a fictional lawyer he called Charlie, played by Idris Elba, who discovers there's a lot more to Molly than was revealed in the salacious tabloid stories.

But he had not even thought about directing Molly's Game until producer Mark Gordon asked him. "I didn’t pursue that job," says Sorkin. "I was asked to direct it and I am very grateful now that I was. I knew I would be risking humiliating myself on a very big stage because of the chance that the movie would tank, But I was willing to do that rather than risk the movie in someone’s hands being something else.

"In other words, if this was going to go bad, I wanted it to be my fault," he smiles.

Although this was Sorkin’s directorial debut, he was by no means a novice on a movie set. "Because I have been a show runner on four television shows that I created, and being a show runner with a distinct voice, I have had experience," he affirms. "And I have been on the set every day of every film that I have written, which doesn’t qualify as directing experience, but I think maybe I was a little bit further along than other first-time directors."

One of his concerns in deciding to direct the movie was gathering the very best cast and crew around him. "Charlotte Bruus Christensen was our DP, and Josh Schaeffer and Alan Baumgarten our editors, but particularly, who was going to play Molly and who was going to play Charlie? And would a Jessica Chastain or an Idris Elba be willing to work with a first-time director and how would that go?

"And thank God they were willing, and they too felt like I wasn’t a first-time director because of the other places where I had had control."

In fact, his first meeting with Chastain formed the foundation of their mutual admiration society. "It wasn’t an audition, because Jessica didn't have to convince me of anything," Sorkin says. "I went simply to discover if Jessica Chastain—Golden Globe-winning Jessica Chastain, two-time Academy Award-nominated Jessica Chastain, who has been directed by Ridley Scott and Chris Nolan and Kathryn Bigelow and Terrence Malick—would be willing to take direction from a first-time director. Or would I be taking direction from her?

"We sat down and exchanged pleasantries and about two minutes into the meeting, she said, 'This meeting is stupid, you should just give me the part.' And I said, 'Yeah, okay, you're right.' And it went on like that from there. Jessica was directing me a lot of the time." He laughs.

On Chastain's part, she had no qualms at all about working with a first-time director as long as it was Aaron Sorkin and he had written the screenplay. "I kind of feel like all the work I’ve done up till now has prepped me to do an Aaron Sorkin script," she says before Sorkin briefly joins her for a reunion hug. "He's a political filmmaker and in his writing there are these themes of justice prevailing against the odds. Which is why we're so inspired by ‘The West Wing,’ A Few Good Men and ‘The Newsroom.’ I think he’s the best writer we have in our industry and you definitely feel his own signature rhythm and style. As an actor, you feel this music that’s within the language of great writers, and because Aaron Sorkin's dialogue is so musical, a lot of the time I was singing musicals with Aaron.

"We’d be on set and someone would say, 'OK, we’re going to turn around, the camera’s going to turn around.' And Aaron and I would sing, 'Turn around.' It was like a game we would play every day when someone would say something and we would just break into a song-and-dance number that would go on and on." She laughs. "I’m hoping in the future he and I can work on something musical together."

Chastain also laughs about getting her brain to work at Sorkin speed, saying it helped that she had learned to perform the work of a wide range of modern writers while studying acting at Juilliard.

But it was by no means an easy shoot. "In fact, it's the hardest thing I've done," Chastain says. "We did 47 pages of dialogue in the very first week, which I've never done before on a film. I thought Miss Sloane was a lot, and this one was double that. But it was like theatre, so we had a great time."

Sorkin has nothing but fulsome praise for his star. "Jessica straps this movie to her back in her very first scene, runs a full sprint for two hours and twelve minutes and doesn’t put the movie down until the end credits roll. That is called 'carrying a movie,'" he says.

Sorkin jokes that his directorial style is to say yes to people when they have really good ideas. Then he adds seriously: "Yes, I do like having the final say, but I am not looking for people to work with who will simply follow my instructions; I am looking for people who are better than my instructions. I am looking for people who will push back and say, 'I think I have got a better idea.' I want people who are bringing their own thing to the table.

"In the editing room, there was nothing better than having the editors say, 'We tried something, and it may sound crazy, but just take a look at it.' And sometimes it is crazy and sometimes it elevates the entire movie. Those are the people that I want to be with, and that is true with actors as well as cinematographers, production designers, editors, cameramen and everybody."

Now that Sorkin has directed his first movie, he wants more. "I love working with great directors and I want to continue to do so. But I had a wonderful time directing this movie and I am very proud of what we did together. So I want to do it again. I would like to direct more movies."