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Aaron Sorkin Embraces the Pajama People

Thanks to his new online screenwriting class, Sorkin has willingly gone to the one place he used to disdain above all else: the internet

"Aaron Sorkin is ready for you," the ominous subject line read.

A few days earlier, in an inquisitive mood, I’d disabled my ad blocker to remind myself what internet advertising looked like. In the few panicked, vulnerable moments before I re-raised my shields, I’d been exposed to — and for the first time, actually clicked on — a Facebook ad, which must have made some algorithm in Menlo Park pretty pleased with itself. The ad promised that if I paid a company called "MasterClass" money, Oscar-winning screenwriter Aaron Sorkin would teach me the tricks of his trade.

The ad called to my cursor not because of any burning desire to be a screenwriter, but because I couldn’t believe that this was the same Aaron Sorkin whose disdain for the internet was once matched only by that of Aaron Sorkin characters who’d loudly declared their own disdain for the internet.

In his younger days, Sorkin stooped to the internet’s level and responded to criticism by posting on forums with sock-puppet accounts. Later he learned to lash out through his scripts and by talking to the media (preferably the print kind), accusing the internet of making us "meaner and dumber" and of being "a bronchial infection on the First Amendment." As The New Yorker’s Richard Brody wrote in reviewing Steve Jobs, Sorkin specializes in "face-to-face confrontations and dialectical jousting," treating "the abstracters, the dematerializers, the face-time reducers as his personal enemies and the enemies of society."

Yet here he was, willing to share his wisdom with (and answer questions from!) the nocturnal nut brigade, the pajama people, the anonymous owners of actual Twitter accounts. Had he mellowed in his mid-50s, softened in his stance as he began to look less like Val Kilmer and more like Elton John? Was this a well-intentioned outreach attempt, an olive branch to the blogosphere? Or was it a ploy, a way for Sorkin to condescend directly while siphoning some of the easy money so many internet commenters make while working from home?

It was time to find out. I opened the email: "Start your screenwriting MasterClass with the man who brought us The West Wing, The Social Network, and The Newsroom," the message said, which was like referring to Ridley Scott as "the man who brought us Blade Runner, Gladiator, and Exodus: Gods and Kings." Sorkin says he’s ready for me? All right; I’m ready for Sorkin.

My goal is to binge-watch all of Aaron Sorkin Teaches Screenwriting. The only impediment is that there’s so much of it: 35 lessons, totaling seven hours, 37 minutes, and seven seconds of concentrated Sorkin (not counting the clicking, buffering, and browser-crashing between episodes). And I’m aiming to do it all in one day, lest my girlfriend dump me because I brought the sadness home. The diary of my journey of Sorkin discovery lies below.

0:50: "There are chunks of [writing] that can be taught, and there are chunks of it that can’t be taught," a sweater vest–wearing Sorkin says in the first taped lesson, sitting in an out-of-focus office. "It’s entirely possible that the way I work and the way I approach it, another person would not be able to relate to at all." We’re 50 seconds in, and I’m ready to request a partial refund. The Facebook ad didn’t have any asterisks.

1:55: "Unfortunately, and I apologize for this in advance, when I’m speaking out loud, as opposed to writing, I swerve all over the road," Sorkin says. "I communicate much better on paper than I do when I open my mouth." This is true. Of course, Sorkin could have scripted these lessons, but after funding Serena Williams Teaches Tennis, maybe MasterClass couldn’t afford his "insane fee."

4:23: For most of this lesson, Sorkin wears one pair of glasses, but in the last shot, he has a second pair around his neck. MasterClass continuity error!

5:10: Sorkin warns us against slipping into his "old habit, back when I was 21 … of just writing snappy dialogue that doesn’t add up to anything." We all did dumb things when we were 21, especially those of us whose dialogue got too snappy, too soon.

7:15: Sorkin, now wearing a suit and sitting on different furniture, is discussing the foundation of drama: intention and obstacle. Intention is what the protagonist wants; obstacle is the thing in his or her way. "If you don’t have that," he says, "then it’s journalism." Ouch.

7:55: Sorkin emphasizes that the intentions have to be solid; if a character is driving across the country just to see a game at Dodger Stadium, we won’t care if he makes it. "Because I’ve been to Dodger Stadium, and it’s no big deal," he says. SHOTS FIRED. Looking forward to Lesson 17, "Vin Scully sucks."

19:29: Sorkin says he’s never written anything that he didn’t wish he could have back and write again, which he admits was "particularly true with The Newsroom. I never felt comfortable writing that show. I never felt comfortable in my chair, I felt like I had a pebble in my shoe … I could write an almost good episode, but I just could not, for some reason, put it together." This is not news to Newsroom watchers, but it might have surprised 2012 Sorkin, who said, "I’ve never been more proud of anything I’ve done than this."

23:41: "I really like romantic comedies, and I’d like to write them," Sorkin says. "No thanks," the women of America answer in unison.

42:10: Sorkin explains that he doesn’t create long character biographies or lists of character traits, because those details would distract from the intentions and obstacles. The downside: Without those backstories to set them apart, some Sorkin characters seem almost interchangeable.

48:52: Sorkin says he tries to fill his writers’ room with smart people who aren’t like him and won’t hesitate to express conflicting options. (Example: "Listen, Aaron, what you don’t understand about the people I grow up with is this.") He adds that their arguments will have equal weight, "at least for a while." And after "a while"? Sorkin doesn’t say, but we can assume that an overruled writer would have an array of enticing options to choose from, such as being replaced or merely being removed from the room.

1:11:11: Sorkin confesses that his computer expertise is limited to asking, "Should I turn it off and then turn it on again?" (Which, to be fair, works pretty well.) Earlier, he called himself "technically illiterate." It’s been said before, but it’s a testament to Sorkin’s abilities that despite his obvious ignorance of/outright hostility toward some of the subject matter, he was not only hired to write two high-profile films about titans of Silicon Valley, but he also pretty much pulled them off.

1:27:32: "The best way you’re going to learn about screenwriting, about writing for television … is by watching movies, watching television," Sorkin says. He’s almost ordering me to quit his class and start the first season of Stranger Things, which I could definitely finish in the time it will take to watch seven-plus hours of Sorkin.

1:30:11: Sorkin cites soccer as an example of why rules are necessary for sports and art to function. "If you were allowed to pick up the ball, run into the stands, run down to the other end of the field, shoot the goalkeeper in the head, and toss the ball in the net, it wouldn’t be a very interesting game," he says. It sounds like he’s describing a cross between basketball, football, and pro wrestling. I’m almost sure it would be the biggest sport in the country within weeks.

1:30:41: Extending the soccer illustration to baseball, Sorkin says, "Abner Doubleday was a freakin’ genius." Aaron, my man — Doubleday was great at Gettysburg, but the belief that he invented baseball is a myth worthy of its own Wikipedia page. By the way, we’re only on Lesson 9, and Sorkin has already made six baseball references (none of which was about Moneyball).

1:42:43: Sorkin spends a lot of time talking about script length. Compared to the typical script, he says — in a tone that borders on humblebrag — his are "a lot longer." As he also notes, though, his dialogue-heavy scripts are showers, not growers; speech takes up space on the page, but action eats up more minutes on screen. Moments later, Sorkin racks up baseball reference no. 7, reminding the viewer that mostly great movies can fall flat if they don’t end in satisfying fashion: "Even when you hit a home run, you are obligated to round the bases."

2:16:22: He’s relocated to a conference room to workshop scripts from five young screenwriters who’ve presumably spilled other screenwriters’ blood to be there. After advising them to keep their descriptions of action scenes concise, he tries to provide an example off the top of his head. Finally, he has one: "Jeanie falls down," he says. Women losing their balance: still a Sorkin staple.

2:17:12: "I don’t know what you kids are doing these days," Sorkin says. "I don’t know what’s ‘down’ with the kids these days. I try to keep my finger on the pulse of the kids, but what with the, um, what’s this … internet thing? Internet? Is that what it’s called?" I like self-aware Sorkin.

2:20:09: A reference to corn in one of the young screenwriters’ scenes sends Sorkin into a reverie that really resonates in the room.

As Sorkin said of The Newsroom, "There isn’t an episode in which there isn’t a reference to a musical." The crowd-displeasing streak stays alive!

3:02:45: One of the young writers reads a script that includes a long, A Christmas Story-esque exchange in which an Asian employee at a nail salon struggles to pronounce the letter "L." "I was very impressed with this joke," Sorkin says.

3:29:17: In a moment of unwitting symbolism (and possible karmic payback for his amusement at the nail-salon joke) Sorkin can’t pronounce "modernity."

3:32:00: "For those of you who don’t know what the overture at the beginning of a Broadway musical is, I can’t help you," Sorkin says. Halfway through the class seems a little late to reveal this.

3:37:52: Sorkin says it was easy for him to identify with Mark Zuckerberg when he was working on The Social Network. "All I had to do was pretend that someone was claiming that they wrote something that I wrote." Someone such as, say, a writer for Friends, or worse, a time-traveling version of Sorkin.

4:25:41: Sorkin sings opera! I’m getting my money’s worth.

4:31:42: In explaining how he trims the fat from his scripts, Sorkin alludes to the Michelangelo line, "You just chip away the stone that doesn’t look like David." He knows the name of the statue, and he knows the quote, but somehow, he doesn’t know who’s supposed to have said it.

4:39:54: If you picked Lesson 24 in the pool for first Studio 60 on the Sunset Strip reference, congratulations! Sorkin slips it in while listing the shows he’s worked on with director Thomas Schlamme. The moment ends faster than the series itself.

4:56:29: Sorkin decides to "do something a little crazy" for lessons 25–32: turn the conference room into a virtual writers’ room and plot out a mock premiere for the fifth season of The West Wing, which he still hasn’t seen. He’s back in his element, looking livelier than before. This is wish fulfillment for fans of the show, but it’s painful to know it’s not real. It hurts even to see Sorkin pretend to swoop in and save John Wells’s West Wing.

5:36:51: Seconds after calling Donald Trump a "Constitutional crisis waiting to happen" (and an hour after flunking art history), Sorkin undermines his credentials as a political commentator by mixing up William Henry Harrison and James Garfield, whom he chastises for failing to wear a coat. According to contemporary accounts, Garfield was wearing a coat when his assassin struck. It did keep him warm, but it couldn’t block a bullet. (Nor could a coat have helped Harrison).

5:43:47: Sorkin is still plotting The West Wing’s Season 5 premiere. "Let’s assume Rob Lowe is willing, let’s bring Sam [Seaborn] back," he says. Now he’s just twisting the knife.

5:56:32: Sorkin comes out in favor of untoasted, unfrosted Pop-Tarts. Discussion about proper Pop-Tart preparation ensues, and one of the writers pipes up to say he doesn’t like Pop-Tarts, period. "Shut the hell up, I don’t know how you got in this room," Sorkin says.

6:39:42: Sorkin interrupts one of his writers’ pitches to reveal an anecdote he heard about the writers’ room for The Office. When they were stuck on a story in Scranton, the writers would "break" an episode of Entourage, just for fun. The catch: Vince had to win the Best Actor Oscar at the end of each one. It’s true! If Sorkin played this game, his solution would be simple: Have Vince hire Aaron Sorkin to produce an Oscar-worthy script.

"I feel like we’ve always been watching this," says my girlfriend, who hasn’t dumped me yet.

7:24:23: "In the final lesson," MasterClass promises, "Aaron offers his parting wisdom and leaves you with one more assignment that will last the rest of your life." One piece of wisdom: Don’t try too hard to placate the critics. For one thing, Sorkin says, it won’t work. And second, he adds, "Dumbo@Dumbo.com doesn’t know what they’re talking about. That’s why they write a blog and you write what you write about." Thirty-five lessons later, I’ve discovered the Sorkin I set out to find.

Way back in Lesson 9, Sorkin instructed aspiring screenwriters to be diagnosticians, saying, "When you see something and it doesn’t work, instead of just being snarky about it, instead of just joking with your friends about how bad this thing was that you just saw, figure out why it’s bad."

I’ve snarked about Sorkin, but I haven’t disobeyed his instructions, because Aaron Sorkin Teaches Screenwriting isn’t actually bad. Like Sorkin’s 385-page first draft of The American President, it’s too long, dwarfing the other seminars available via the same site. And like Sorkin himself, it recycles some material. But it works, both as a tutorial and as a window into his world. He’s self-deprecating and cocky, flipping back and forth between dismissing himself as a schmuck and adopting what Rob Reiner dubbed a "Trust me, I’m Aaron" attitude. He’s clever and corny, mindful and myopic, hopelessly hidebound but more likable than he was when Will McAvoy was his mouthpiece. Maybe it’s Stockholm syndrome, but after spending 7 1/2 hours with Sorkin, I think the guy is growing on me. And maybe that works both ways; Sorkin still isn’t living the full online life, but we know he’s not a strict isolationist.

After I finish the last lesson, I notice a new email in my inbox. "Aaron thanks you," its subject line says. Not so ominous now.

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