Hollywood's most celebrated and scrutinized screenwriter ups the ante for his directorial debut as he floats a 'West Wing' reboot (with a black president) and reveals the anxiety that fuels his ambition: "I always feel like my life depends on writing something good."

On a late summer evening, Aaron Sorkin wandered into a pizza shop, folded himself into a counter seat and ordered a plain slice, with a Pepsi to wash it down. He was stomach-grumbling hungry and in need of a distraction.

Down the street, at the Toronto Film Festival, his poker thriller Molly's Game was playing for the first time before a crowd of some 1,500 festivalgoers. Sorkin didn't need to be in his reserved seat at the Elgin Theatre to know exactly where in his film the audience was. He took a knife and fork to his slice — "a mortal sin if you grew up in New York," he acknowledges, but he couldn't risk a spill on his premiere-night suit — and began, in real time, running through the movie, the first in his three-decade career as Hollywood's most celebrated and scrutinized screenwriter that he directed as well as wrote.

"Did I ever change that thing I wanted to change?" he panicked. "That sound right there of the skate on the ice, did we get that right?" His mind raced, concerns ping-ponging between the response of the audience and that of the film's inspiration, the infamous poker princess Molly Bloom, who was seeing the fictionalized retelling of the bleakest chapter of her adult life play out for the first time in a packed theater.

"I was very nervous," Sorkin says more than a month later, seated in his dimly lit office on the Warner Bros. lot in Burbank, surrounded by framed photographs of his heroes: Arthur Miller, George Bernard Shaw, Tennessee Williams and Hunter S. Thompson. Dressed in his uniform khakis and a button-down shirt, his eyes gaze toward the window: "I'm still very nervous."

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When Sorkin's directorial debut, starring Jessica Chastain and Idris Elba, comes out on Christmas Day, its success will be measured against the unfairly high bar of his own past work. "I'm proud that when I write something, expectations are high," he says, "but it's not an advantage." The fact that Molly's Game tests an entirely new creative ambition — Aaron Sorkin, movie director — only raises the stakes. For the 56-year-old auteur, whose name is synonymous with a certain hallmark style of percussive dialogue and whose association is damn near a guarantee of widespread attention, the ability to experiment quietly is a luxury he gave up long ago. Sorkin doesn't need those images of Miller or Williams or Shaw looming above to intimidate him; he does that all by himself. "Whether it's an episode of television, a movie or a play, I always feel like my life depends on writing something good," he says, "and in a very real way, it does."

At this point, the industry's highest-paid screenwriter, who earns $4 million a script (and another $1 million if the film gets made), could make a fine living by simply rehashing his past successes. He already has agreed to tackle a live staging of his first breakout, A Few Good Men, for NBC, though now he reveals he'll need to push back its planned spring 2018 airdate another year. Filling out a cast led by Alec Baldwin (as Col. Jessep) has proven a challenge, and he can't quite figure out how to make the 1980s-set play feel fresh. There's also a standing offer from the same network to reboot The West Wing, which Sorkin considers on occasion. When asked if he'd introduce a Trump-like figure in his fictional White House, he winces, arguing that the current president holds no appeal for him, fictional or otherwise. "Trump is exactly what he looks like: a really dumb guy with an observable psychiatric disorder," he says. Sorkin's preferred scenario, he tells me, would involve "Sterling K. Brown as the president, and there's some kind of jam, an emergency, a very delicate situation involving the threat of war or something, and [President] Bartlet [played by Martin Sheen], long since retired, is consulted in the way that Bill Clinton used to consult with Nixon." How he brings Allison Janney's C.J. Cregg or Bradley Whitford's Josh Lyman into the new scenario is where Sorkin gets stuck. So, for the time being, fans will have to settle for reruns.

To Sorkin's amazement, Molly's Game came considerably easier, though not without its own backstage drama: He battled over the release date, cut ties with longtime agent Ari Emanuel and watched as emails referencing his alleged financial woes were picked apart in the wake of the Sony hack. But now the film is done, and all he can do is sit back and wait on the audience — to say nothing of the awards groups, which are already screening the movie and will determine its place in this year's wide-open Oscar race. "It's this huge weight on his shoulders," says Molly's Game producer Mark Gordon, who also produced Sorkin's last screenplay, Steve Jobs, "because the expectation from everybody is, 'If it's Aaron, it's going to get nominated.'"

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Sorkin fell in love with the sound of dialogue long before he had a grasp of what the words might mean. His schoolteacher mother and lawyer father would take him, the youngest of three, to Broadway shows as a kid: He saw Man of La Mancha at 6 and Who's Afraid of Virginia Woolf? at 9. By the time Sorkin hit his teens, he was vice president of the Scarsdale High School drama club; when he left for Syracuse University, his plan was to become an actor.

In the summer of 1983, he moved to Manhattan and, as legend now has it, found himself holed up for the night at an ex-girlfriend's apartment, where he fed a few blank sheets of paper into a semiautomatic typewriter. What emerged became the bones of his debut play, Removing All Doubt, about a bunch of high school pals who get back together in their 20s. Writing it was an intoxicating thrill, as was the adulation that quickly followed. That first play began attracting actors like Matthew Broderick and Kevin Bacon to do stage readings; and his second, a one-act play about show business, got an off-off-Broadway run and helped land him a theatrical agent. Then came a call from his sister, a lawyer headed to Guantanamo Bay to defend a group of Marines accused of killing a fellow soldier. Sorkin turned her predicament into a Broadway play, and then an Oscar-nominated film starring Jack Nicholson and Tom Cruise called A Few Good Men.

That first brush with Hollywood was instructive in good ways and bad. A studio executive on the film insisted that the characters played by Cruise and Demi Moore sleep together. Sorkin strongly disagreed, arguing that these two young lawyers are in way over their heads on the murder case and would be doing nothing but working. "The note I got from the studio executive was, 'If Tom and Demi aren't going to sleep together, why's Demi a woman?' " he reveals now. "I think about that note when I read about someone wondering why we never see Molly with a boyfriend. No one ever asked why Brad Pitt didn't have a girlfriend in Moneyball."

After A Few Good Men, offers began flooding in, and drugs followed. "You know how I got addicted to cocaine? I tried it," Sorkin said during a commencement address he delivered at his alma mater in 2012. Staring out at a sea of early 20-somethings, he opted not to sugarcoat the decade or so he spent high. "The problem with drugs is that they work, right up until the moment that they decimate your life." Throughout Sorkin's darkest years, of which he has only faint memories, he convinced himself he needed those stimulants to fuel his creativity. It was a phone call from Carrie Fisher, then a virtual stranger, who made him consider the alternative: "I know you think you're not going to be able to write," he remembers Fisher telling him, "but I promise your writing is going to get better."

This coming April, Sorkin will celebrate 17 years drug free, and in that time, he has written five movies, four television series and a Broadway play and won an Oscar for penning The Social Network. He has no plans to slow down, either. The day after we meet, he heads to New York for the first table read of his Broadway revival of To Kill a Mockingbird, set to debut in 2018 with his Newsroom star Jeff Daniels as Atticus Finch. From there, he'll write his Lucy and Desi movie, with Cate Blanchett attached to play Lucille Ball. Though he hasn't made much headway on the plot — the appeal was her and their relationship, he says — he reveals that it will be told against the backdrop of a single production week at I Love Lucy, from table read to audience taping. It's a familiar construction for Sorkin, who has offered peeks behind the scenes of a TV show many times before: on Studio 60 on the Sunset Strip (with late night), Sports Night (sports) and The Newsroom (cable news).

In all the years that Sorkin has been at it, however, the process hasn't gotten any less torturous. "I have two gears," he says, puffing on a cigarette: " 'I'm stuck, I've got nothing, and I've already written the last thing I'm ever going to write,' and 'It's going well.' " To get from the former to the latter, he relies on a succession of showers (as many as eight a day, each time a kind of do-over) and a mix of long walks or drives in which he acts out whatever scene he's working through. Sorkin once was so absorbed role-playing a scene from The Newsroom that he lunged into a mirror in the sprawling Hollywood Hills home that he lives in alone and broke his nose. Pictures of his swollen face later zoomed around the internet, where in recent years Sorkin has taken more than his share of lumps.

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Type Sorkin's name into Google, for instance, and a deep well of material turns up, much of it railing against him for various creative offenses. A persistent critique is that he diminishes his female characters, putting them in situations where they have to be redeemed by men. Such views will likely re-emerge when Molly's Game is released, though he's hoping to remain outside the fray and let the work speak for itself. "Once I put it on the screen, I don't have — and I shouldn't have — anything to say about how an audience member receives it," he tells me, before acknowledging that the criticism can periodically get under his skin: "Sometimes it stops being about the movie or the play or the episode of television, and it gets personal. Sometimes it's a character diagnosis by someone who's never met or spoken to me [and] who wasn't within miles of what they're writing about."

It certainly won't hurt to have Chastain, one of Hollywood's most vocal feminists, in his corner as he sets out to promote Molly's Game. A story about patriarchy, featuring a self-made woman whose high-stakes poker empire lands her at the center of an FBI investigation, was an easy sell for the actress, and she gives him ample credit for making it his directorial debut. "Aaron could have told any story he wanted, and he chose to tell this one," she says, describing the film as "an incredible social commentary about a woman who's struggling to find a voice and have success in situations where men make the rules and those rules change based on their whims." Ironically, the movie began filming the day after the 2016 election, and it was a note that Sorkin wrote that morning to his teenage daughter, Roxy, and her mother, Julia, a former studio lawyer and Sorkin's ex-wife (the couple was married for nearly a decade and remains fiercely tight), that put Chastain at ease about her new collaborator and the world that they would now inhabit. A sample line of the excerpted letter, which later zoomed around the internet as well: "Grandpa fought in World War II … I will not hand his granddaughter a country shaped by hateful and stupid men. Your tears last night woke me up, and I'll never go to sleep on you again."

More recently, as a wave of sexual misconduct allegations has rocked Hollywood, Sorkin's response again impressed his star. In this case, it was his support of Chastain's early advocacy on behalf of the victims following a pair of bombshell reports of Harvey Weinstein's alleged abuses. "It's a very scary thing to be a woman in the industry where men are making the rules and stick your neck out and say, 'I don't care. I'm going to defend these victims and amplify their voices,' " she says. "Aaron Sorkin was the only person in the industry who sent me an email. It said, 'There's not a day that goes by that I'm not proud to know you.' " Sorkin has had similarly powerful conversations on the subject with Roxy, now a junior in high school, who has filmmaking aspirations of her own. He wanted to be sure his only daughter knew that she could fight back if she ever were to find herself in a situation where a man forced himself on her. Roxy flipped the scenario on her father, asking why he was teaching her to defend herself and not teaching those men not to be predatory. "I told her, 'You are 100 percent right, but until all the men who have to change, change, I want you to scream your lungs out,' " says Sorkin. "Then I showed her a Three Stooges short to teach her how to go for the eyes."

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Sorkin didn't initially set out to tell a story from a woman's point of view. In fact, he only agreed to sit down with Bloom in July 2014 as a favor to a lawyer pal, who was representing her memoir. But by the time his hour with her was up, he knew he'd found his next movie. "Molly was not at all whom I expected her to be," explains Sorkin, "and the fact that idealism could be found in a story set against the backdrop of high-stakes underground poker was a big part of what drew me."

For the next six months, Sorkin and Bloom met regularly in his office, where he peppered her with questions about her past, from her early years as a champion skier to her later ones running bicoastal poker games that made her a target of both the FBI and the Russian mob. On many of those days, Bloom, a self-described Sorkin megafan, would leave her session with a homework assignment. Once, it was a paper about the specificities of the slope she used to ski down. Another time, it was one about the recruiting and vetting process for players. "Let me tell you, getting a writing assignment from Aaron Sorkin is not your most fun day," she laughs, recounting the many hours she poured into her prose.

The more time the two spent talking, the more fascinated Sorkin became by the impact that Bloom's highly demanding father had on her life. It's a piece of her story that she'd left out of her book entirely, and, she admits, "It was harder to have those conversations with Aaron because not only was I getting personal about my life, I was getting personal about someone else's." That relationship between Bloom and her dad ultimately became a central throughline of Sorkin's screenplay, reminiscent of how the charged one between Steve Jobs and his daughter plays out in his 2015 film. Says Sorkin, "The easiest thing in the world to do is for one father to empathize with another father."

Bloom remained hands-on in the development process and became a big proponent for casting Chastain. Other A-list actresses including Emma Stone had been considered, but Chastain offered a winning combination of vulnerability and maturity, and within minutes of sitting down with Sorkin to discuss the role, she had wowed him. "The meeting took place at midnight in my hotel suite," he tells me, attempting to keep a straight face. "I answered the door in my bathrobe. You know, the way all meetings happen in Hollywood." We both laugh nervously, and then agree, given the deplorable nature of what had already come out, that it's probably too soon to be making a Weinstein joke. I ask if he'd tried a similar line the night prior, when he introduced Chastain at Elle's Women in Hollywood event, where sexual harassment was topic A. "No," he cringes, seemingly horrified at the mere suggestion. "I made the decision to get Jessica up there and let her talk, and if you can refill anybody's coffee pot, do that." Adding to the discomfort that evening was the fact that some of the other actresses whom he had met about the role were in attendance: "It was like the scene from Four Weddings and a Funeral," he says, "when Hugh Grant is at the table with all of his ex-girlfriends."

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In the end, the decision to direct Molly's Game was, in large part, a way for Sorkin to protect Bloom's story. Unlike others who had approached her about putting her life onscreen, Sorkin wasn't interested in the shinier aspects of Bloom's story, be it the money or the bold-faced names like Ben Affleck or Leonardo DiCaprio who had played in her games. Though it was producers Amy Pascal and Gordon who had proposed the idea of Sorkin helming it — "It was a story about the things that Aaron cares about: human resilience and human dignity," says Pascal, "and it was the right size movie to start with" — the desire to maintain the sanctity of the story ultimately convinced him to say yes. In the interim, he sought the advice of several others (Warren Beatty, David Fincher and Elvis Mitchell among them), and then hired a trainer to ensure he was physically prepared. At one point, he even got a prescription from his doctor to try to kick his smoking habit, though he later rationalized that he couldn't risk mixing its side effects with the stresses of directing his first movie.

By all accounts, however, Sorkin slipped into the role of director with phenomenal ease. "Once he decided to do it, he became the director: He knew exactly whom he wanted in the movie, he knew exactly what he wanted it to look like, and he knew exactly how he wanted to shoot it," says Pascal, who shares a long history with Sorkin from her prior tenure as an executive at Sony, which released The Social Network and Moneyball. Elba, who was prepping his own directorial debut (crime drama Yardie) while shooting Molly's Game, was similarly impressed, both by Sorkin's willingness to delegate and his ability to appear calm. "Aaron trusted the people whom he gave jobs to," says the actor. "He didn't try to be an actor or a DP or even the writer on set. He stayed in his lane as the director."

Still, there were hiccups. The first came early, when Sorkin, who had already made a deal with Sony to write the Wall Street drama Flash Boys, decided he wanted to make Molly's Game instead. In fact, he was so eager to get started on it that he told Pascal he was willing to be paid scale, cashing in only in success — just enough, he joked in an email that later went viral as part of the Sony hack, to let him "pay Roxy's tuition in the meantime." He would later come to see another hacked email from a top Sony executive to Pascal, which read, "Don't let Aaron guilt you by mentioning Roxy's tuition." Says Sorkin, "I was like, 'What? That was a joke. I was telling you that you don't have to pay me.' " With some distance, he's able to appreciate the irony of the subsequent "Sorkin is broke" narrative that took hold. Then he offers, unprompted, "I believe that Amy speculated [in those hacked emails] that I was sleeping with Molly, too. Neither of those things were or are true."

A tug of war over the budget of the film — which moved from Sony to Gordon's eOne-backed company with a $9 million boost from distributor STX Entertainment — came next. "Aaron had a very strong point of view and very strong vision, and he wasn't going to make the $15 million version of the movie," says Gordon, recalling with a chuckle some of the tense conversations the pair had early on. "I'm laughing now, but he pushed me to my limit and beyond." The two finally settled on a number in the $30 million range, which by and large allowed Sorkin to make the movie he set out to make. (He kept his $4 million fee, paid when the film was still with Sony, but plowed his $1 million production bonus into the budget.) More tense conversations followed, as Sorkin grew concerned that his collaborators lacked the expertise to release the movie in the manner to which he had grown accustomed. For the first time, he had neither a major studio behind him nor his frequent producing partner Scott Rudin, whom he historically relied on to herd an aggressive campaign. STX's initial launch ideas seemed geared to a different kind of movie than the one Sorkin believed he had made, and though he had brought the picture down below its contractually mandated length of two hours and 15 minutes, he now worried that it was still a few minutes too long. The release date was another sore point. Early on, the distributor proposed February, outside of the traditional awards corridor; Sorkin, for whom that recognition is hugely important, pushed back. "Of course you don't want this movie to open in February," he explains now. "It's good."

It was in the midst of these heated back-and-forths that Sorkin decided to part ways with Emanuel, his representative of 17 years, and sign with rival CAA, which had been courting him for some time. Sorkin felt intense loyalty to his longtime agent, who had seen him through a heavily publicized drug relapse in 2001 and, in the years since, made him the only writer in Hollywood whose deal includes a clause prohibiting a studio from replacing or rewriting him. But his mounting concerns over the Molly's Game release strategy introduced a new variable into the mix — and gave CAA its opening. The agency brought Sorkin in for a meeting with its head of marketing and presented him with an elaborate, awards-focused plan to roll out the film. By the time it was over, he was convinced that making the leap was now necessary. "It wasn't just about me anymore; it was about the movie and everyone who worked on it," says Sorkin. Nevertheless, he adds, "leaving Ari was every bit as difficult for me as my divorce."

Back in Toronto, Sorkin takes a final swig of Pepsi and returns to the Elgin Theatre in time to see the audience's rapturous response to Molly's Game as the credits roll. He is ushered backstage for a private moment with an emotional Bloom, and then onstage with the stars, including Chastain, who, like him, has just been thrust into the Oscar conversation in a meaningful way. Then he slips into a car, and as it weaves its way to the afterparty, his longtime publicist begins reading aloud the first wave of tweets and reviews, each one more effusive than the last. "It's the kind of stuff you write in your head as you're falling asleep," says Sorkin, who, for just this moment, is satisfied and at peace.

SORKIN'S NEXT ACT(S)

To Kill a Mockingbird

Sorkin has been spending time in New York in recent weeks, attending table reads for his Broadway revival of To Kill a Mockingbird, set to debut in late 2018. The play reunites him with The Newsroom's Jeff Daniels (who will star as Atticus Finch) and producer Scott Rudin. It brings the auteur back to the platform where he got his start, which — if forced to choose — is still his favorite. Bartlett Sher is attached to direct the play, and, per Sorkin, "the cast and design team we're putting together is a murderers' row of seasoned theater professionals."

Lucy and Desi

Though he has yet to write a single word, Sorkin already has a star (Cate Blanchett as Lucille Ball), a distributor (Amazon Studios) and the support of Ball and Desi Arnaz's children. What he knows at this stage: His latest peek behind the scenes will examine a single production week at I Love Lucy, from table read to audience taping. For Sorkin, the pioneering TV personalities offered several appealing factors, beyond simply the backdrop. "Their relationship is very interesting to me," he says. "And she is interesting to me. I didn't know that she was accused of being a communist."

A Few Good Men

Sorkin has committed to reviving his film breakout, A Few Good Men (based on his own play), as a live play for NBC. "It's something I've been talking to people about for years," he says of the live TV format, adding with a laugh: "I just didn't think it would be my play." Though the net recently announced that Alec Baldwin will play the Col. Jessep role inhabited by Jack Nicholson in the 1992 film, Sorkin is still mulling the project. "What does it look like on TV? The fact that I can't give you an answer yet is one of the reasons I want to [push it to next season]."

This story first appeared in the Nov. 29 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.