In 2011 Hollywood was rocked by the news that the FBI had opened an investigation into what would soon become the most infamous poker ring in history. It all started when a hedge fund manager lost $25 million playing alongside acting's biggest stars—Ben Affleck, Matt Damon and Tobey Maguire among them.
The criminal investigation and effect on the industry's A-listers became the biggest story of the summer, revealing delightfully sordid details like dark backroom clubs, secretive games in high-priced hotel suites and Ponzi schemes. Rumors and news of the poker ring trickled out for years afterwards, thanks to courtroom proceedings and paperwork that was slowly released to the media. It had all the markings of an expensive, testosterone-filled blockbuster movie. Even Leonardo DiCaprio was involved.
The only problem that Hollywood's inner circle tightened even harder around the details of the ring, and nobody would talk. It's hard to make a movie based solely on conjecture. Until Molly Bloom, the woman who ran most of these high-priced poker tournaments for a decade before being arrested by the FBI, decided to write a book. That's where Jessica Chastain comes in.
The Oscar-nominated actress is the star of the upcoming Molly's Game, due to hit theaters on November 22, which tells the story from the point of the view of Bloom herself. Anyone who enjoyed the fast-paced, take-no-prisoners woman of steel that Chastain produced in the recent Miss Sloane will find another unlikely heroine here.
The actual story of how Bloom came to power in the poker ring is something that truly cannot be made up. She began as a cocktail waitress and had been hired by a wealthy real estate investor to play hostess at a gambling tournament he was throwing at Hollywood's infamous club The Viper Room. That night's game was attended by all of the movie industry's biggest players, and Bloom called them all out by name in her memoir: Todd, Bruce, Tobey, Leo. Molly came away with several thousand dollars in tip money that evening, and suddenly she had a new career.
Cocktail waitressing at a a game run by her boss quickly turned into running her own high-stakes games and run-ins with groups like the Russian mob (hence the arrest), and she became notorious among the elite class of gamblers that included directors, actors and producers.
So how do you go about making a movie that simultaneously skewers many of the movie industry's biggest players, most of whom still don't like talking about the incident to this day? First you have to cast the lead role. For Aaron Sorkin, who makes his directorial debut with Molly's Game, playing Molly was not for beginners.
"What you needed was one of the finest actresses in the world," he explained at the movie's Toronto International Film Festival press conference. "There was a nuance to this role, a strength, a very interesting sense of humor. Jessica fit the bill like no other, and it was a matter of wooing her to get her to put her considerable reputation into the hands of a person who had never directed a movie before."
Yet Chastain describes taking on this role as an easy decision; the magnitude of tackling the salacious subject matter didn't even dawn on the actress, because she was so drawn to the character of Molly Bloom. She has made it no secret as of late that she's looking to change the landscape for women in Hollywood, and she believes it all starts with her movie selection process.
"I'm now really aware of what I'm putting out into the world," Chastain said at the press conference. "What am I doing to contribute to the industry in a positive way? To me that means playing women who are complicated, who aren't angelic or a sexy object of desire. I'm interested in playing authentic women who make a lot of mistakes and who can get quite messy sometimes."
To prepare for playing a woman who was all of those things (and, on top of them, someone who has plead guilty for a federal crime), she needed to learn everything she could about the poker industry and Molly's role in the Hollywood poker ring. She admits that when she first Googled the story, she found it impossible not to judge her. This was a woman who helped Tinseltown's biggest players win millions of dollars, after all.
But then Chastain met Molly, and went to watch poker matches that were similar to what went down in the movie, and began to form an understanding of what she went through.
"The more time I spent with her, the more I started to understand the position she had been forced into," she said. "She was in an industry that was male-dominated and where they made all the rules. Her livelihood was dependent on whether they [the poker players] felt like she was giving them enough attention. I had a lot of empathy for her for that."
While Chastain learned plenty during the making of Molly's Game, including the in's and out's of the competitive poker industry and, one would imagine, more than her fair share of gambling lingo, she left the set with a few takeaways for her own life, as well. Most importantly, she wants women to take a stand whenever they can.
"Molly makes a lot of mistakes in the film, and for me the first was when her boss tells her she has an ugly dress and shoes," explained Chastain. "She changed who she was to fit into what she thought she needed to be, to find power and success. Just wear the ugly dress and the ugly shoes and make people respect you for more than just what you present physically"