Aaron Sorkin Teaches You How To Win the Lottery

Notes from his MasterClass on Screenwriting

If you were casting a movie and needed someone to play a teacher of screenwriting, you would probably pick someone like Aaron Sorkin to play the part. He is a middle-aged white man. He wears sweaters. He has oval, bookish-guy glasses. His hair is still very good; a few strands of it artfully fall over his forehead in a way that may or may not be engineered. He makes insightful, put-it-on-a-poster observations while also saying “ah” or “um” with regularity, like a smart person who is not so brilliant as to seem unapproachable.

Aaron Sorkin wants to teach you screenwriting, for a new website called MasterClass that has a mysterious business model. They got some of the biggest stars in given fields to sign on as teachers — there’s Werner Herzog on filmmaking and Annie Leibovitz on photography — with more to come. Being a teacher (I’m not going to say “master”) means recording hours of teaching material in the form of direct-to-camera addresses or workshops where the teacher is interacting with students in a classroom setting. These are big names — quick, name a more famous screenwriter or photographer other than Aaron Sorkin or Annie Leibovitz who is also still alive. They must have paid them handsomely for their participation, and yet the class is $90.

I am suspicious of all of this.

Should you plow ahead, here are things you may notice while taking Aaron Sorkin’s screenwriting class:

  • I may be confusing him with other middle-aged white men and their tendency toward a lack of self-awareness, but I am surprised by how humble Aaron Sorkin genuinely seems to be. He references an element of a previous show of his as “good” and then hastily corrects himself: “Not that I think it’s good writing…” and not even with undertones of “Peep how humble I am!!!” Maybe part of this is being a recovering addict, as Sorkin famously is; maybe when you’ve hit bottom, it’s impossible forever after to think of yourself as hot shit.
  • He identifies himself early on as possibly a crap teacher because he has thought patterns that don’t move in particularly linear and helpful ways. He is a man who has written a lot about politics and knows something about expectation-setting — set the bar low, and it’ll be easy to top it.
  • You will find yourself endeared, despite yourself.
  • Aaron Sorkin once had a male character say “You’re a woman!” to another male character as an insult, so Aaron Sorkin and I are still not entirely okay.
  • Within the first three classes, Aaron Sorkin achieves what no other screenwriting class I have taken has accomplished (and reader: I have taken some), in two ways:
  • First, he explains the fundamental elements a good script — intention and obstacle — in a way that an entire giant copy of Robert McKee’s “Story” will not put quite so clearly. It’s the simple idea that you are sunk if your main character doesn’t want or need something that is believably difficult for them to get. He describes intention and obstacle as a clothesline that runs throughout your script — you need both for it to stand up at all, and only when you have both can you start adding more stuff to it.
  • The second thing Aaron Sorkin does that no one else really does is acknowledge that making shit up is hard. Figuring out what’s going to happen in a story is really hard! The actual writing of it, the hands-to-keyboard part, is the fun part, but so much of writing is the figuring-shit-out part, and if you feel like you’re bad at it and it’s painful now at least you know that Aaron Sorkin finds it painful too.
  • Aaron Sorkin specifically calls out writing scripts full of snappy dialogue in which nothing happens, making the viewer watching think back on his past work and say softly to herself, “Oh.”
  • There are a series of student workshop sessions in which Aaron Sorkin sits in a room with five students and workshops opening scenes of scripts. Some of the scripts are incomprehensible and he gently asks “Did everyone understand what happened in this scene?” in a way that will bring you back to every creative workshop class you have ever taken.
  • At one point, Aaron Sorkin makes a very dry joke about a continuity error that a student doesn’t understand as a joke and it’s awkward because Aaron Sorkin doesn’t want to acknowledge latent power structures.
  • At the end of one session, Aaron Sorkin makes a big show of saying “Here’s your homework for tonight! Let’s all sleep on this!” And then, in the next episode that’s supposedly the next day, Aaron Sorkin and the students are all still wearing the same outfits as before. “So did anyone have a chance to think about this overnight?” he says. No, Aaron, I was apparently sleeping in my clothes? It makes you doubt everything: Are these kids real screenwriting students or are they actors? Are their lines, their work, all of it, scripted? What is the truth, MasterClass??
  • During the student workshop Aaron Sorkin brings out a second pair of glasses, a reading pair, that he wears on a chain around his neck like an 19th-century New England schoolmarm, and you’ll will yourself further to not be endeared.
  • Aaron Sorkin is only really cringe-worthy one time, and it’s when a conversation goes on way too long about a pitch he’s making to his students (IF THAT’S WHAT THEY ARE) on a show called “Mission to Mars.” It’s actually really clever — a workplace drama/comedy set entirely on a spaceship en route to Mars, where everyone knows they will probably die. But when the student-actor-kids don’t show as much enthusiasm as he would like, Aaron Sorkin says “Mission to Mars! Come on!” in the way that people watching sports will sometimes chide players for not making obvious connections on the field. The kids remain unmoved. You can see Aaron Sorkin wondering if the end of manned space missions has killed a sense of wonder in our nation’s youth.
  • The class ends with Aaron Sorkin exhorting us to make original work that matters, which is inspiring in the way that Aaron Sorkin speeches can be if you’re a certain type of earnest person who likes Aaron Sorkin movies and television shows.

But in the end, I wonder what the point of any of this is (beyond returning the investment of whatever VC money was put into MasterClass as a whole). Unlike so much of continuing education — knife skills, art history, woodworking, photography — screenwriting is nearly useless as a form of art to practice or enjoy in its own right. A script, historically, is not a consumable product on its own. You can’t Kickstart or self-publish it. The movie is the product, and movies (and TV shows) have one of the highest barriers to production imaginable because they are, for the most part, fucking expensive to make at even minimum levels of quality. Because money is important, gatekeepers become important, and the usual rules apply to who tends to get past the gates. Very few people sell scripts, very few scripts actually get made into films or TV shows, in numbers such that the widest point of the funnel — writing a spec script without connections to the industry — approximates buying a lottery ticket.

Maybe this screenwriting course is more about learning how to appreciate film, or getting good enough to eventually get a job in a writer’s room, or just pass the time as an amusing hobby, but it’s not really sold that way. It’s sold inspirationally, as a way to make art, and in that sense, Aaron Sorkin might be a bit too Aaron Sorkin for the job.


Laura Olin runs The Awl’s newsletter, Everything Changes, and as a long-time professional Democrat is actually a secret giant Sorkin fan. You can follow her on Twitter at @lauraolin.