John August

Scriptnotes, Episode 649: The Comedic Premise with Simon Rich, Transcript

Scriptnotes Transcript

The original post for this episode can be found here.

John August: Hello and welcome. My name is John August, and you are listening to Episode 649 of Scriptnotes. It’s a podcast about screenwriting and things that are interesting to screenwriters.

Today on the show, which ideas are inherently funny? We’ll discuss what makes a comedic premise and how you develop and execute upon that idea. To do that, we have a very special guest. But first, Drew, we have some news and some follow-up.

Drew Marquardt: We do. We’ve talked about the quest to make a Harry Potter series, and the uncomfortably public search for a showrunner.

John: As a reminder, they said, “Oh, we’re gonna make a Harry Potter series and we’re gonna go through a series of rounds of different writers who might become the showrunner. It got kind of public in a way that made me feel eugh.

Drew: It was a bake-off, right?

John: Yeah.

Drew: We have news that Warners has made their pick. It’s Francesca Gardiner of Succession along with director Mark Mylod, who also did Succession and Game of Thrones and The Last of Us and all sorts of stuff. They seem like a really good team to do that. I would say going into this, I was skeptical that anybody would want to step up to do this, especially in the bake-offy situation, but it looks like they ended up with some really talented people. I wish them luck. I think it’s gonna be a hard road ahead, but we’ll see what they’re able to make. That Harry Potter series will eventually probably come to your screens.

Second bit of news is very, very local here. For the last 20 years I’ve had this blog, johnaugust.com, that we reference every week. One of the things I’ve done on the blog over the years is have these little short snippets of scripts in there as examples, for like, here’s an example of dialogue, here’s what this looks like. They’re just these little boxes that show a little bit of screenplay format. To do that, we created this thing called Scrippets, which Nima Yousefi, who works for us, initially created. It’s super useful. It’s a plugin that you can install through WordPress. It’s been really great and useful.

The trouble is time moves on, and the plugin is no longer working well under the most recent versions of WordPress. Somebody out there listening probably does this for a living or as a hobby and has created WordPress plugins. If you are that person and you would like to step in and update this plugin for us, that would be fantastic. I’m sure there’s somebody out there who knows what they’re doing and could get this working. Scrippets, by the way, became the whole basis for plain text screenwriting. It has a long legacy, so you would be helping continue that legacy. If you’re that person and you want to help us out, just email Drew, ask@johnaugust.com, and he will be the person who can point you in the right direction.

With that done, it’s time for our main guest. Simon Rich is a writer and showrunner who created the series Miracle Workers and Man Seeking Woman and the film American Pickle. He’s also an author, who’s written novels and short story collections, such as Spoiled Brats, Hits and Misses, and New Teeth. His new book, Glory Days, is out July 23rd. Welcome to the program, Simon Rich.

Simon Rich: Thanks so much. Thanks for having me.

John: You have twice been my One Cool Thing, although Craig’s read your books and liked them too. Way back in Episode 179, which was the conflict episode, I talked about Spoiled Brats. In particular, one of my favorite short stories of all times is Gifted, a thing that I probably go back and read every year or two. I think it’s just such a brilliant short story.

Simon: Thank you so much. It really means a lot to me. Big fan of this show and a fan of your writing. It’s just thrilling to hear that the work resonates with you, truly.

John: For folks who have not read Gifted, the premise of it is that essentially this couple gives birth to what’s clearly the antichrist, clearly a demonic creature, and they’re so obsessed with getting it into the best private schools in New York City. I want to talk about the comedic premise and how we get into all that and why it’s a short story versus something else. But before we do that, I’d love some background on you, because I know you from your writing, but I don’t know basically anything about you. If you can tell us the backstory of Simon Rich.

Simon: The backstory, I grew up definitely obsessed with comedy, for sure. I would say particularly premise-driven, absurdist sketch comedy, Kids in the Hall, Mr. Show, The State, the chunk of SNL that was after Update where you were allowed to be a little bit more serial. I was also really obsessed with premise-driven genre fiction.

As much as I loved Kids in the Hall, I was equally obsessed with people like Richard Matheson or Stephen King or Bradbury or Philip Dick, Shirley Jackson, just anyone who would hook you at the end of the first page and make you keep reading. I was really always thinking of writing through the lens of what is a premise, what is a hook that I can generate that is strong enough to get people to keep turning the pages.

John: That’s great. What were the initial things you actually wrote? Were you in a stand-up group? What were the ways you were exploring this idea, like, “Here is the premise. Here is how we hook people in.”

Simon: My first book, which was called Ant Farm, it was a collection of short stories that were so short that they basically don’t even have narrative. Each piece is basically a premise, and then it ends before it’s developed in any way. That was pieces I’d written for The New Yorker and other magazines.

Basically, it wasn’t really until I got to Pixar – I was a staff writer at Pixar and I worked for Pete Docter writing on Inside Out. It wasn’t until I got there that I really started to think more in terms of narrative and storytelling. I kept being obsessed with premises, but that’s when my writing veered more into a traditional narrative space.

John: Great. In our Bonus Segment for Premium Members, I definitely want to talk about magazine writing and your short stories in magazines, because I really have no idea how that whole world works. Clearly, that was a great entrée for you. But let’s get to Pixar. Was that your first time being a professional staff writer where you were going in to do a job and your job was to write funny stuff?

Simon: No, my first job was at Saturday Night Live.

John: I’ve heard of Saturday Night Live. It’s a show. For people who don’t know, it’s a very successful comedy program.

Simon: My first book had come out. Like I said, it was just a list of premises, and so SNL was a pretty good fit. I never had to really learn any narrative tools, because a lot of the sketches at the time just ended with everybody jumping out of a window. We literally got a warning once – or not a warning, but a very polite request from Seth Meyers, as one of the head writers, just asking us if we could, just for fun, have a week where no sketch ended with every character jumping through a plate glass window while a random ‘80s song played, because that was our go-to sketch out. It was just starting to get on everyone’s nerves.

It wasn’t really a story-centric show. That show was all about how do we get people to laugh by any means necessary. I learned so much about comedy and premise writing and dialogue there. I was there for four years. Then it wasn’t until I got to Pixar that I started to actually think about, what is this three-act thing.

John: Because this is a show that’s largely listened to by aspiring writers, they want to know how do you get hired into Saturday Night Live. Obviously, at this point you had Ant Farm. People could read that as a sample that, “Oh, this is a guy who understands what a joke is. He understands what a premise is.” But were you also submitting a packet? What was the process of getting hired at Saturday Night Live?

Simon: I had no packet. I had Harvard Lampoon. Colin Jost was two years ahead of me. I think he just handed my book to Seth and said basically, “I think you should read this and give this writer consideration.” I wasn’t really thinking about getting into TV and film at the time. I was a magazine writer at that point. I had another book that I was working on. I don’t think I had a television agent at the time. I had a book agent. I fell into it, but I’m really grateful that Colin thought of me for the show.

John: what I love about your description of your backstory in your biography is that you keep omitting things that were clearly important steppingstones along the way, like Harvard Lampoon. Harvard Lampoon is of course a great classic training ground for comedy writers. A lot of Saturday Night Live writers, a lot of Simpsons writers came out of Lampoon. Talk to us about – did you go into Harvard thinking, “Oh, this is a place I want to find myself.”

Simon: I went in desperate to write for the Harvard Lampoon, desperate to get better at writing. But I did really want to be a short story writer. It’s such a strange ambition.

John: Talk to me about that. Who are the short story writers that were inspiring you to say, “This is my calling.”

Simon: I would say when I was 18 years old, the writer that I was probably most obsessed with was TC Boyle, whose work has been adapted into a lot of films. Probably the people listening know Road to Wellville is one of them. But TC Boyle is this extremely funny, premise-driven writer. He’s written a lot of historical novels, but his short stories to me were just mind-boggling in terms of how original they were, how funny they were, and how had they incorporated various genres. He was never tethered to a specific genre. He was willing to write a Sherlock Holmes-inspired story and then go straight into a Western. He was a huge idol of mine. I remember going into one of his readings freshman year and just being too afraid to even meet him afterwards. That’s really what I wanted to be.

I would send my stories to every magazine on earth. There were a lot more magazines back then. The way that you would submit – it was before online submissions, actually, when I started. You would send a self-addressed stamped envelope along with your story, because the magazines were too cheap to mail you back. You would send your little short story. Under your name at the top, you had to put how many words it was to warn them what they were getting into. I was like, “This is 7,000 words.” I always felt pressured to keep them short, because I knew if that number was too big, they might not even read the first sentence.

I would send it off to places like Playboy and Esquire. These were magazines at the time that were publishing really good fiction. The New Yorker. Then I would always put the Lampoon as my return address, because the mail was more reliable coming to our office than to the dorm rooms. Every month, everybody would watch as I would get my stack of rejection letters.

Then I eventually started to get nicer rejection letters. I remember I did get a nice rejection letter from Playboy telling me to submit more. It was awesome. A couple others where they had actually written something back, as opposed to just sending you a form letter, which is the typical response, where it’s, “Thank you so much, but we… ” I still have some of those in a drawer somewhere. Some of them were really cool looking. I think the Paris Review had a really cool letterhead. Then I started selling some pieces. The first magazine that I sold to with any kind of consistency was Mad Magazine.

John: That’s great.

Simon: Then eventually, I started to place pieces in The New Yorker. Ant Farm is a collection of my most successful stories by that age. But again, they weren’t really stories. They were just kind of comedic premises without any elaboration whatsoever.

John: Let’s talk about the comedic premise, because one of the things I love about your short stories is I think if someone just handed me a book blind and said, “Read these short stories,” like, “Oh, this is Simon Rich.” I recognize a consistency of voice, despite the genres, despite whatever else. It’s all focusing on characters who are in violation of the social contract or that they have this opportunity to break the social contract, and the repercussions there, and there’s one thing that’s tweaked about the world.

It’s a very relatable premise of, it’s a dad who’s taken his family on the train and recognizes it was a big mistake because it’s taking too long. He goes to the bathroom, and he meets the troll there who tries to con him out of… The troll is the addition to the thing that makes it just not a grounded-in-reality story.

But let’s talk about, with that story or really any of your stories, what is the comedic premise? Is the comedic premise the thing that’s different or the thing you’re actually going to be able to explore by going into that? The example I gave you is a story about what it’s actually really like to be a parent and just give in and just let your kids do what they want to do. What is the comedic premise for you in those kinds of situations? Is it’s what’s different or what you can get out of it?

Simon: I would say that there are comedic premises that are really, really funny but are not necessarily emotionally – they don’t have what I would call narrative legs necessarily. For example, when I was at SNL, I wrote a lot of sketches with John Mulaney and Marika Sawyer. John Mulaney actually reads the audio book for Glory Days. I’m supposed to plug the hard cover, because it’s more expensive, but everyone should obviously listen to this one instead.

But we wrote a sketch called Rocket Dog. The premise is that Tracy Morgan is a film director and he has directed an Air Bud style film called Rocket Dog, the inspirational story of a boy and his dog and a rocket that they fly. It becomes clear, after watching the clip based on the in-memoriam sequence that runs at the end, that many dogs died, and also some people, during the making of Rocket Dog. That’s what I would call a comedic premise, but I don’t know if that necessarily is a premise that has narrative legs. It’s a premise that can support hopefully a three-minute-and-a-half sketch.

John: Let’s talk about that, because essentially what you’re describing, that is the punchline. The premise is the punchline where you’re getting to, and you have to establish the context around it. Talk about that specific sketch. What was the initial pitch on it? What was the process of going from, “What about this sort of space?” to, “There’s now something written down. There’s something that we’re going to get approved. There’s something that we’re actually going to rehearsal.” Can you walk us through what that’s like?

Simon: The pitch is the hook. The pitch is you reveal in an in memoriam that – you show a bunch of dogs. That’s the pitch. It’s like, okay, great, that’s a strong turn, a strong comedic reveal. How do we sustain it? The answer, of course, sketch comedy rules, as we had to figure out new ways to escalate it and show multiple in memoriam sequences and make sure that we’re escalating the carnage at every turn. Also, we have to write a lot of jokes and have reaction shots from Kristen. You just kind of go through the mechanics of sketch writing.

A big important execution thing for that is what music do we play for the in-memoriam sequence. Marika Sawyer, one of the funniest people ever, wisely pointed out that it had to be a pretty uplifting, jaunty song. Otherwise, it would just be too sad to watch all of these dead dogs float by. She selected Life Is A Highway, which is just perfect. Still to this day, it’s one of my daughter’s favorite songs, actually. To this day, when it comes on our Alexa, I just think of hundreds of murdered animals.

John: That’s great. But I want to get a little more granular in terms of, okay, you have this idea. How is it written up and how is it presented to the group? How does it get approved to be in the episode of the week?

Simon: Oh, like in the process at SNL. At SNL, the writers are really allowed to write whatever they want, for better or for worse. That’s probably an idea that we had on Monday. Then on Tuesday night is when we would’ve actually written it into script form. That’s just the three of us in a room pitching jokes. Typically, we would write a long outline first. That was every single joke option in order. We had a rough shape of a sketch, but there’s many, many alts. But they’re arranged loose, chronologically. All the entrance jokes are at the top. All the premise-establishing jokes are at the top.

John: When you say writing, is this just in Word or something? What are you doing this in?

Simon: I always like to write the first outline in Word. It would always be a long Word document. Then we wouldn’t switch into script form until we basically were sick of writing jokes for it. Then it’s about just picking your lanes and reading it out loud many, many times.

We were lucky that one of us could act. That was actually really important for Mulaney to basically read all the main parts, so we could actually hear whether or not it was good, because Marika and I are not performers. If we didn’t have somebody with comedic timing, we would have to just hear it in our heads, which is not as successful a way to vent comedy. It’s better to hear somebody who’s actually funny read it.

John: Over this course of – this is Tuesday night you’re writing or Wednesday night you’re writing?

Simon: This is Tuesday night into Wednesday morning, 2:00, 3:00, 4:00 a.m. Then you turned it in. Then Wednesday there’s this big table read where you hear cast doing it and the host doing it for the first time. Now it’s down to 40 sketches, I think, or even less. But when I was there, they would read sometimes up to 50 sketches.

John: Wow.

Simon: They would pick a dozen, and those would be fully produced, and then they would cut four during dress rehearsal on Saturday night.

John: In this Wednesday table read, so you already said Tracy Morgan will play the director. You’re already making those choices. Tracy doesn’t have time to prep it. He’s just reading it cold, right?

Simon: Right.

John: Great. Then hopefully, the sketch gets selected. You figure out how to produce it. Then you do it in the dress rehearsal. Then you see if you’re actually going to do it like for the big show. Rinse and repeat hundreds of times.

Simon: Yeah, exactly. You had everyone’s help for the rest of the week. Once the sketches are picked, you have a whole day on Thursday where you have essentially a room that is a very traditional LA style writers’ room. We had one day a week where it felt like working for a sitcom, where you come in at a normal hour, and everyone argues about what to order for lunch. You’re spending a day collectively looking at scripts, figuring out as a group how to improve it, how to pitch alts, how to make scenes more efficient. There was one day a week that felt like traditional sitcom writing feels like.

John: You have dozens of sketches you have to do, so you can’t spend the whole day working on Rocket Dog.

Simon: No, but they would split into two tables. There’d be five or six sketches maybe per room. Every eight-page script got at least an hour of attention. It always felt supported by the writers’ room.

John: Then at the end of the writers’ room day, the three of you would go back with the Rocket Dog sketch and get it into its final shooting shape? There’s obviously the rehearsal before there’s the dress, and then there’s the final show. How much would change between the rehearsal, between the dress and the final?

Simon: A lot is changing after the rewrite table, although not that much typically. I would say maybe it’s 10 or 20 percent different after a Thursday. It has to be pretty close to the goal line for them to pick it. It’s probably a new ending, definitely some improved jokes, but it’s essentially the same thing. The casting remains the same. The structure usually remains the same. Friday and Saturday you’re really mainly focused on production, like what are they wearing and approving props. At SNL, you’re approving everything, because the writers produce their own sketches at SNL.

John: Now, how many years were you working on Saturday Night Live?

Simon: Four seasons.

John: Four seasons. You went from there to go to Pixar?

Simon: Yeah, I went straight from SNL to Pixar. It was maybe a few days in between the end of the season and my first day. It was such a culture shock, because I’d literally been coming from an environment where we would spend six days making a 90-minute piece of entertainment. At Pixar, it would be 10 years to make the same number of minutes. I mainly worked on Inside Out. Just to put it into perspective, I think I was maybe the second or third writer on that. It had already been a year maybe of development before I showed up. After I was gone, it was I think five more years before it came out. It’s just absolutely glacial, especially compared to late-night television.

John: I’ve been to Pixar and on their campus. It’s such a strange place. Lovely, but super calm. They’re riding their bikes all around. I heard them say things like, “Let’s do a three-day offsite about this scene.” I’m like, “Oh my god.” That just terrifies me. They’re drilling down and being so granular on certain things. I don’t think I could survive it. But tell me about what you were doing on a daily basis. What words were you putting out?

Simon: That job, I guess I would describe it – it was a lot, I think, like being a staff writer for an animated sitcom is what I would compare it to. With the director, in this case Pete Docter, being the creator showrunner. It’s Pete’s movie. It’s Pete’s idea. It’s Pete’s vision. He’s the showrunner. Then as a staff writer, you’re working with him but also with storyboard artists and co-directors to help Pete break the story. Then I would be assigned scenes to write. It’s pretty similar to what I imagine it would be like to write for an animated sitcom.

John: At any given point, was there a fully completed script, or were you just doing pieces and little chunks? Could you ever print out a script and say this is the script for the movie at this state?

Simon: No, because it’s so iterative. Every single sequence is at a different stage. Some things are in animatics. Some things are just in boards. It’s a very complex process. Part of it is just because it’s really hard to animate a movie.

John: What you’re describing, people should know, is very traditional for how animated movies are done. Disney does it this way. Pixar does it this way. Most places are doing it this way. Then weirdly, I’ve had the opposite experience, where I write a script and turn it in, and they make that script. For the stop-motion animation I’ve done for Tim Burton, there’s a script. Yes, there are storyboard artists and other things, but they’re figuring out how to execute the script, rather than this being this back and forth.

It’s a very different experience for writers who are doing what you’re doing, which is having to constantly react to what other people around them are doing. It’s not theater, but it’s just like you’re almost documenting what the current state of the story is.

Simon: Totally.

John: I want to drill in a little bit more here, because you said this is the first one that you’ve learned about character in three acts and moving beyond that initial premise, because a sketch or your shorter short stories are literally just the premise, and it’s just the punchline. Here, you have to keep moving on beyond that. What stuff did you learn at Pixar?

Simon: I think the clearest explanation of what I learned is you get to see how much I ripped them off. I wrote a story when I was there called Unprotected, which is the story of a very conventional premise. It’s a teenage boy, and he is struggling to figure out a way to lose his virginity, so essentially the premise of a million summer movies for many decades. What made it unique is that it was told entirely from the point of view of the condom in the boy’s wallet, who is waiting and waiting and waiting and waiting to be used. It is just Toy Story. It is just a straight one-to-one version of Toy Story, an R-rated Toy Story, where it’s a coming-of-age story about a young person told from the perspective of this anthropomorphic object. It was so blatant.

I remember coming to campus when The New Yorker ran it. I remember walking past the lamp, the little lamp statue, and a storyboard artist pointed to me and was like, “Toy Story, right?” I was like, “Yep.” I didn’t get in trouble or anything. But that was just me really trying to see if I could take the story moves of literally a famous Pixar movie and just ape them for my own creative purposes. That’s something I’d keep doing. But I’m not shy about it, because Pixar would do the same thing.

We would constantly map out the story for hugely popular movies and just say, “Okay, how can we turn our project into this? What would happen if we copied it exactly?” Invariably, you’d find, we can copy these aspects exactly, but not these, because we have a slightly different agenda. That process of modeling and emulation is another really important thing that I learned from them, in addition to just literally copying them.

John: One of the things I think you can get away with so well in short stories – you can also do it in SNL sketches – is be able to take a piece of existing IP and completely just subvert it or ask the question you could never ask in the initial IP. The title story in Glory Days is Mario’s journey into middle age and what he’s wrestling with. Can you talk to us about that premise and what you were trying to explore and what was the initial instinct? Was it the wholly formed idea, or was it just like, “Oh, wouldn’t it be funny to do a story about what Mario’s life is actually like?”

Simon: The initial instinct was I read an article on my phone, I’m sure, that was like, “Super Mario debuted in 1984, 40 years ago,” or whatever. I said, “Oh, Mario’s turning 40. That’s hilarious. What is his midlife crisis like?” I was really excited to dive in, especially because I knew I’d be able to get to write the entire thing in Mario’s singular voice.

John: “It’sa me.”

Simon: Yeah, which is this incredibly offensive two-dimensional stereotype Italian accent. I was really excited to be able to take a voice like that, which is so dumb and so lazy, and just imbue it hopefully with some humanity and some pathos. You find out that he lost all his coins. He got so many. They had whole rooms of coins that he just pocketed. But he made a rookie mistake in the business, which is he trusted a friend to manage his money. Yoshi just took him for all he was worth. He’s estranged from the princess.

John: Who he still needs to rescue.

Simon: Who he needs to rescue for the millionth time. He says he’s starting to suspect that she’s getting kidnapped by Koopas on purpose, which of course is really offensive. But that is what he believes.

John: His relationship with Luigi is strained, and because of Luigi’s partner, and there’s lots of very specific things.

Simon: Luigi got sober, which is great, because he was gonna die. But he’s married to this extremely boring guy, Kalami, who is really nice and super loaded and has this fancy job, but is just constantly getting on Mario’s case, like, “You need to get a job.” He actually makes Mario fill out a resume, which is this very tragic scene, because Mario is like, “I have experienced saving princesses.” Kalami’s like, “You need to put down your plumbing experience, because that’s where the jobs are at in this market.” Mario is just kind of devastated.

It ends up being a story of different types of winning. Mario is a character who has a very specific idea of what it is to win. You get a lot of points. You climb that castle thing and you jump and grab that flag thing. Then you stand next to the princess while Japanese text scrolls slowly by your face. That’s what winning means. In midlife, through the story that he lives through, he kind of comes up with different priorities and a different understanding of what victory can look like.

John: You said that the premise was Mario’s turned 40, what’s Mario’s midlife crisis like. How much did you figure out about everything else you just described before you sat down to start writing, or was it just the process of writing that you explored all the other things?

Simon: Great question. Basically, what I do is – the first thing, still to this day, and this is what I’ve been doing since I started writing as a kid – until I have the premise, I basically don’t do any story or comedy work whatsoever. It’s just finding the premise.

Once I got the premise, then I do a lot of what I guess you would call exploratory writing or free writing, where I’m like, “Okay, I really like this hook. I think it has a motion and legs. It makes me laugh.” Then I just write a bunch of just random scenes. If it’s close third person, there’ll be third-person scenes. If it’s first person, there’ll be first-person paragraphs, just to test it, to make sure that it’s fun, that I’m gonna have a fun time doing it.

Then I take a big step back and I outline it. That process is, I would imagine, very similar to the one that most screenwriters go through. I take a big step back and I say, “Okay, what is the act one, act two, act three.” I don’t do that unless I’m really in love with the premise and in love with the point of view.

John: You say you don’t want to start until you really know the premise. By the premise, you mean the hook, and do you think what the engine is that will get you through the story?

Simon: No, I don’t necessarily have the engine. I think I just have the premise and the point of view. Is it going to be first person, is it going to be close third.

John: Let’s also define close third person, because it’s a term that people may not be familiar with. Third person is obviously we’re looking at the character doing stuff, so “he did,” “she did,” that kind of stuff. But close third person is like the camera’s almost right behind the person’s back and we’re only seeing the stuff and knowing the stuff that they would know.

Simon: Exactly. Screenplays, they are pretty much written in what fiction writers would call the omniscient third, where it’s like, this is what is happening. This is literally what you are looking at. There are exceptions, like if you’re Shane Black or whatever, where the stage directions have a personality maybe or they’re written in the first person by the screenwriter.

John: They’re also written in the first-person plural. That’s why the “we hears,” “we sees,” the feeling like we are here together watching this movie, but we don’t have insight into just one character. We can have a global view.

Simon: You never write a stage direction like, “As she crosses the crosswalk, she sees a bird out of the corner of her eye and recalls a childhood song.” That would be very hard for the viewer to notice in a wide shot.

John: If you establish the premise and the point of view before you go into it, then you’re free writing to find what are the things that are interesting there, find what do you think the little bits and moments might be.

Simon: It’s like test driving a car or something. I just want to know that it’s going to be fun, because writing a story is really hard. I want to make sure it’s going to be a good time. It’s like, is it gonna be fun to write in this voice for a few weeks?

John: How much time are you spending on that free writing period?

Simon: Not too long. I would say a couple of days and then I’ll say, “Yeah, this is gonna be fine.” Then I have to do the challenging thing, which is break the story.

John: Then breaking the story, this is your outline phase, which is basically what are the beats. For a story like Glory Days, how long is your outline? How detailed is that outline in terms of these are the actual scenes that are gonna happen?

Simon: I don’t go as spartan as cards on a board, like, I would in a TV room, but I’m pretty close. I would say a sentence or two sentences max per scene. I just try to figure out what is – I guess I can give away that story. It doesn’t really matter. The situation, the call to action is the princess gets kidnapped by a Koopa. But the issue is that he has horrific back problems. Mario has spent the entirety of his adult life just running and jumping at full speed, at full intensity.

John: Absolutely.

Simon: Smashing many bricks.

John: With his head.

Simon: With his head or his fists. It’s unclear how he’s doing it. But either way, it’s very arduous and rugged. His doctor, Dr. Mario, no relation, tells him that he needs intense spinal surgery, or else he might lose the ability to walk. He says, “You’re gonna lose the ability to walk.” He also speaks in Mario voice, of course.

Mario can’t make it through eight worlds, plus mini worlds, all the way to Koopa’s castle, unless he fixes his back. If he has the surgery, he’s incapacitated for a year. He finds this back brace, this revolutionary back brace that he can wear, but it’s really expensive. He needs money to get the back brace so he can rescue the princess. That is the act one goal is he’s gotta do it.

The low point at the end of act two is, by this point he has robbed his brother, because Luigi and his husband refuse to – they basically say, “We’re not going to enable your toxic relationship with the princess anymore. We’re not gonna lend you any more money.” Mario, in a really emotional low point, he steals Luigi’s Amazon packages and sells them online so he can get enough money for this back brace. Then he sends it over to the guy, and the guy starts asking him for garlic over the phone. That’s when he realizes that it was actually Wario.

John: The whole time.

Simon: It was a scam. He was tricked. Now he has nothing. He has no back brace. He has no money. He’s robbed his brother. That’s the act two low point. The princess is sending him texts like, “Where the hell are you?” He’s got no way to save her and no way to save himself. Then act three is redemption. The way I actually outline the stories is no different than the way I would outline an episode of Man Seeking Woman or a film.

John: Talk me through that process. In this outline, you’re really establishing what are the story points, how much story do I need to tell this whole story, because what you’re describing is great for a short story. It’s not gonna be enough for a movie, but there’s plenty there for what this is supposed to be. I think one of the great things about a short story is that you don’t have to have anyone’s permission to make this parody of Mario, whereas a movie or anything else, you couldn’t do it.

Simon: There’s a lot of freedom that you have in fiction that you don’t have as a screenwriter. Fictional characters never show up late and hungover. You don’t have any budget conversations. You don’t have any studio notes. The amount of control and freedom that authors have over their books is amazing compared to the amount of control most screenwriters have. I’m not a hugely famous writer, author, but I wield as much power over my books as Vin Diesel does over the Fast and the Furious franchise.

John: Absolutely.

Simon: I could say to my editor, “I want to intentionally misspell this word.” My editor will be like, “I don’t think that’s a smart idea, but okay, Mr. Diesel.” It’s on that level. It’s such a different level of freedom than I have when I’m working in TV and film.

John: Absolutely. I’ve done three books. I did the Arlo Finch series. It was great and liberating to actually have final say over every last little detail. Every piece of world building that I wanted to do or not do was there because I wanted it specifically there. At the same time, you don’t have the benefits of everybody else there to make a big final thing.

As we wrap up the premise, I want to talk about your experience actually making things with other people and having to do longer-form things, your two series or American Pickle. These are situations where you had this comedic premise that was originally a short story and you had to build it out into – let’s take Man Seeking Woman into a series. What is that conversation, and what needs to change in order to make that a sustainable thing with other people involved?

Simon: I love collaborative writing for a number of reasons. The biggest reason is just that – and I’ve talked about this already – you learn so much, or at least I’ve learned so much, from working with other writers. I learned so much at SNL from writing with Mulaney, writing with Marika, writing with Seth Meyers and for Seth. Seth was my boss. He was an amazing teacher and mentor. I learned a lot from trying to emulate him but also just literally asking him questions, like, “How do I do this? Why did you make that choice?”

Same thing at Pixar. I feel like I learned a ton working for Pete on Inside Out. But I would also just ask him and everybody else, “Hey, when you were doing Toy Story 3, why did you make this decision? How did you come up with this story point? What was your process?” You learn, or at least I’ve learned a ton from the collaborative work that I’ve done. You have access to not just the brilliant minds of other writers, but like you said, all these other brilliant artists who are contributing in such meaningful ways.

I would say the thing that I miss the most when I’m writing fiction is the music, because it’s such an unbelievably powerful, visceral, emotional tool. My younger kid has this Cocomelon book where you press a button and it sings the ABCs, and you press another button and it sings, “The wheels on the bus go round and round.” I always fantasize that I could have a button in my short story collections when it gets to the emotional denouement of a story. Mario is in the hospital bed holding Luigi’s hand. If you could press a button and John Williams plays, that would be dope. I really miss that tool.

But the thing that it gets you is freedom but also control. I think that a show like Man Seeking Woman, I’m really proud of the show. I loved running that show. But I would have to be a megalomaniacal psychopath to say that that show is mine the way my books are mine. I didn’t write all the episodes. I certainly didn’t act in any of them. I did not make the monsters. I definitely didn’t compose or sing the song at the end, in the third act of Episode 307, which is the only reason why the emotional arc landed.

There’s so many aspects of it that I cannot take credit for, whereas the books, for better or for worse, they are completely mine. They’re more communicative. I don’t know if they’re necessarily better, but they’re more personal.

John: Yeah, for sure. We have two listener questions that I think might be especially appropriate for you. Drew, can you help us out with these listener questions?

Drew: James in Washington writes, “Given the current state of the industry, should struggling screenwriters think about writing novels if they have good stories that can’t find a pathway to the screen?”

John: What’s your take on that, Simon?

Simon: It’s a great question. I think everybody should try it, just like I think everybody should try stand-up comedy. Stand-up comedy, there’s nothing more pure than that. You can just stand on a stage. People don’t even need to know how to read. They can be illiterate. You can just tell them anything. The only reason not to do it really is because you are bad at it or don’t like it, which you can’t really learn until you try it.

I tried stand-up in high school and learned very quickly that I was bad at it and also that I hated it. But if you’re okay at it and you like it, then you might be willing to put in the thousands of hours it takes to become great at it.

I think it’s the same thing with fiction. Give it a shot. If you’ve never written fiction before, it would be unusual for you to start off being great at it. But you might enjoy it and you might feel like it’s worth pursuing. If you really like it, then you might be able to put in enough time to become great at it. Then you’ll have this whole other avenue through which to express yourself, where you don’t need to ask for permission. You don’t need to get funded. You don’t need to pitch. You can just write it, and then it’s in the world and it’s finished.

John: Absolutely. I think implicit in James’s question is, “It’s tough to make a living as a screenwriter now, so should I be writing novels because it’s easier to make a living as a novelist?” It’s not. It’s really tough to be a person who writes books. It’s tough to be a writer who is making a living in general. Your ability to have complete control over everything and to not have to get anyone’s permission to do a thing is great. You don’t need permission to write a screenplay either. But if fiction appeals to you, try it.

One thing I’d also recommend is listen to what Simon’s saying about the premise. Some premises work really well for fiction or they work really well for a short story, they work really well for a play, but they’re not gonna necessarily work well for a movie. If you have an idea that is really interesting to you but it doesn’t feel like a movie idea or a series idea, then give yourself permission to explore it as what it wants to be.

Simon: Totally.

John: Let’s try a second question here.

Drew: Macklin writes, “I’ve recently found a love for playwriting again. Is there an unknown downside to publishing work in other areas, like novels or plays, or establishing an online newsletter or something?”

Simon: A downside? Not that I can think of. It’s a blast. Writing fiction is so fun. There are a lot of screenwriters out there that I think would be really good at writing fiction and might enjoy it. Playwriting is not something I’ve done a lot of, so I can’t speak to that. But it’s really thrilling to be able to just wake up in the morning and go right into it and not have to ask for permission.

John: I would agree with you. I’m curious about how do you budget your time in terms of thinking, “Oh, I should do a short story now,” or is short story writing what you do when you don’t have other Hollywood stuff that you need to do? What’s the Simon Rich calculus for writing short stories?

Simon: As strange as it is to admit it, I am a short story writer. That is how I identify. That is what I’ve been doing since college. Everything else is, I don’t want to say intrusion, because that makes me sound ungrateful for the Hollywood work. But Glory Days is my 10th book. I have done other things. I did write a couple of novels. I’ve run television shows. But even the shows that I ran were based on my books. Most of the movies I’ve written or scripts I’ve written have been based on my short stories.

I know it’s a weird thing to have devoted one’s life to, and I’m not going to try to defend it. But I am like a short story writer who sometimes adapts his work into other mediums, basically.

John: What you’re doing though, it’s analogous to some people who’ve spent their entire life writing on SNL though, because you’re writing very short, focused things that are in a very specific form, and that’s what feels really natural for you to write. Focusing on that and finding a thing that you write that you love sounds great.

I do wonder if sometimes on the podcast, because we’re mostly talking about feature writing or TV writing, we steer people into belief that that’s a thing that people should be aiming to do. There’s lots of other great ways to write that are not those things. It was important for us to have you on just to talk about people who have that instinct, who are funny, who have that instinct like, “This is a funny idea.” Just because it’s a funny idea doesn’t necessarily mean that a feature or a TV series is the only way to express it.

Simon: Totally. Totally. I think the voice thing, that’s a big one. You might find that you really love to write in the first person and from an unusual point of view. That’s what I miss the most when I’m writing scripts.

I would say when I was running Man Seeking Woman, those three years were the one time in my writing career where I really was focused on television more than fiction. I really felt at that job like I had as much freedom as one could ask for. The reason why is because it was at the absolute peak of an insane bubble.

Also, our show is unbelievably cheap. A lot of forces had to conspire for us to be allowed to continue to make that show that nobody saw. The Canadian dollar was at a historic low. We were shooting in Toronto. If you look at a 150-year graph of the Canadian dollar, there’s this unaccountable three-year dip that perfectly coincides with the history of Man Seeking Woman. I don’t know what happened. There’s a maple syrup shortage or something.

But anyway, working on that show, I had a lot of freedom. I could write and approve my favorite premises. I have Bill Hader playing Hitler in a pilot, and nobody blinked. But I still missed writing in the first person. I missed being able to tell an entire story from the perspective of a horse or a baby or a talking condom. Even though I could have characters like that on a show and I could write dialogue from unusual points of view and-

John: But you didn’t have insight into the inner thinking of that character. The way that fiction writing is like whispering in somebody’s ear is just a very special connection.

Simon: It’s very specific. Even in the best of times, which I would say Man Seeking Woman was for me, I found myself missing my incredibly stupid narrator voice.

John: Great. It is time for our One Cool Things, where we recommend stuff to our audience. My One Cool Thing this week is Howtown. It’s a series on YouTube by Joss Fong and Adam Cole. They try to answer one question in every episode, so things like how do we know what dogs can see, how do we really know COVID’s real death toll. It’s just incredibly well produced, smartly researched. But also it just looks really good. It’s smartly written. Check out the series Howtown. There’s a bunch of episodes that are up now, and they’re gonna keep doing more of them. But check it out. YouTube, Joss Fong and Adam Cole. Simon, do you have a One Cool Thing for us?

Simon: I do. I’m on vacation for a couple weeks in Wisconsin, seeing some family. I found a book on the shelf of the Airbnb that I’m at, which I am obsessed with. I’m also finished with it. Hopefully the last 50 or 100 pages aren’t terrible. But I’m gonna recommend it anyway. It’s called Dr. Eckener’s Dream Machine, the historic saga of the round-the-world zeppelin, by Douglas Botting. It is just a phenomenal, true, nonfiction account ofana actual 11-day round-the-world zeppelin voyage that took place in 1929.

John: Wow.

Simon: Basically, when you think of zeppelins, you think of the Hindenburg, which is the correct thing to think of, because that wasn’t a one-off accident. These things exploded all the time, catastrophically. The way that they worked is there was a big bag of hydrogen, and then basically a fire would run an engine that was right next to the bag. If any sparks cut from the fire to the bag, everyone would die every single time. But it worked one time. This is about that one time. The descriptions of them circumnavigating the globe are stunning, because they’re not very high off the ground. They’re only at times about 300 or 500 feet off the ground.

John: Oh, wow.

Simon: They go over continents that have never seen or heard of air travel. They describe in Siberia people essentially, for the 20 hours that they’re going over Siberia, everyone is terrified and thinks that they are an actual alien or a monster.

John: That’s amazing. As you bring up zeppelins, or this specific story, there are so many premises that can pop out of this. What you’re describing in terms of zeppelins just basically want to explode, telling it from the zeppelin’s point of view, telling it from the insurance company that has to insure zeppelins. There are endless possibilities there. Or the actual story of this journey could be something fascinating too. It’s a great One Cool Thing.

Simon: Thank you.

John: That is our show for this week. Scriptnotes is produced by Drew Marquardt. It’s edited by Matthew Chilelli. Our outro this week is by Nico Mansy. If you have an outro, you can send us a link to ask@johnaugust.com. That’s also the place where you can send questions, like the ones we answered today. You can find the show notes for this episode and all episodes at johnaugust.com. That’s also where you’ll find transcripts and sign up for our weekly newsletter called Inneresting, which has lots of links to things about writing.

We have T-shirts and hoodies and hats. You can find those at Cotton Bureau. You can sign up to become a Premium Member at scriptnotes.net, where you get all the back-episodes and bonus segments, like the one we’re about to record with Simon about about getting your short stories published in magazines. Simon Rich, an absolute pleasure talking with you finally after all these years.

Simon: Thanks so much. Thanks for having me. Big fan of the show and fan of yours as well.

[Bonus Segment]

John: Simon, you publish these stories, before they’re in your books, in many, many magazines around the world. New Yorker obviously is the one I think about the most, but McSweeney’s, GQ, Vanity Fair. I have other friends who have don’t his as well. Megan Amram does this. BJ Novak does this. Can you talk me through what the actual process is for you right now? Your short stories are gonna be great. Do you just say, “I got a new one,” and they just say, “Great. Here’s a couple pages.” What is the process for letting them know that you have a short story that you want published?

Simon: Good question. It’s a smoother process now than it was when I started 20 years ago. Should I walk through the genesis of it?

John: It’s different if you’re Stephen King. Talk us through the process.

Simon: In the early days, I had no agent, and I would just send envelopes with my stories – that’s dating myself – to various magazines, with a self-addressed stamped envelope, saying, “Would you please read it?” They would either not write back at all, or they would send back a form, rejection letter, a rejection slip, I should say. A lot of times they were just actually horizontal strips of paper.

John: They didn’t want to waste a full sheet of paper.

Simon: Exactly. There’s no need to. The next step was I started to get some positive feedback from some editors at magazines saying, “We like this,” or, “We read this,” or, “We think this is really funny, but it’s not for us. Please submit again.”

Then all of a sudden, you have a contact. You have an editor. Then you have their email address or even phone number. Then it becomes a little bit easier, because you can ask them, “What sort of things are you looking for?” Then they might write back, “We’re doing a travel issue in six months. You have any travel pieces?” or whatever. The bullseye appears more cleanly through the fog as you start to know editors. Then once you have an agent, then it becomes much, much easier, because they of course have a lot more contacts probably than you do typically as a writer.

John: Now, at this point, you tell your agent, “Here’s the short story that I have.” Then are you discussing where is the right place for it to go, are there preexisting contracts or negotiations? Would any of your stories be appropriate for any of these places? What are you thinking as you do that?

Simon: I learned from a really early age that when I feel pressure to sell things, it doesn’t necessarily make my writing worse, but it makes it less interesting. I only really felt that pressure once, which tells you how privileged my career has been. But it was during the writers strike in 2007, ’08. Was that-

John: 2008, yeah.

Simon: Yeah, around then, yeah. I had started writing for SNL, but I was four weeks in. I still hadn’t earned the minimum for health insurance. I was doing just fine. I had a book deal. But I did feel some pressure to make some money. I started pitching aggressively to every single magazine under the sun and wrote a lot of pieces that I think are just not in my voice. It was more just like, “Okay, this is what’s in the news,” or, “This Maxim Magazine knockoff seems to be doing a lot of this sort of piece.” I started to write a lot of things just chasing freelance money.

Now, because I have the luxury of thinking of things in a less mercenary way, I just write the entire book, basically. I don’t show anything to anybody really. Then I just send the entire manuscript to my agent, who sends it to The New Yorker, and they pick the ones that they want to run. That way, I’m not thinking about, “Oh, they probably want a Trump piece,” or whatever.

John: Totally. Thinking about it this way, so you’ve written all the short stories that are gonna be a part of a book. I notice in Glory Days, you have it broken into one, two, and three. There’s some sectioning to it, and yet each of the stories does stand on its own. I’m hard-pressed to find a connecting thread between them. But they all feel like this is one book that is together.

You’ve written this book. You’re sending it to your editor. It’s going to The New Yorker. What is the purpose of getting those published in The New Yorker? Is it from them paying you directly, or it’s exposure for the book that you’re trying to do?

Simon: My goal as a writer always is for people to read the stories or listen to them or experience them in some way. That is the absolute only goal that I have. I hope that people will give these stories a chance, read them, listen to them, relate to it, connect to it in some emotional way, and I’ll feel less alone in the universe. That’s why I make this stuff. One hopes that they have enough cash that they could spend their days living that artistic life.

John: With these short stories in this most recent collection, The New Yorker might say, “Oh, we want this short story.” Would they ever come back to you with a note on the short story, or is it gonna be published as it is, because you also have your book editor who’s going through and reading the stories too. Do you get stuff from both sides?

Simon: I don’t really get big edits anymore. But I do get a lot of suggestions and feedback about what you would call line edits, which are really useful and really helpful.

I also get fact checked, which you wouldn’t expect for a fiction writer. But it’s incredibly useful. The fact checkers at The New Yorker are the best in the world. They’re basically the equivalent of what we would call script supervisors. They’re finding inconsistencies. They’re saying, “Why are they eating lunch if it’s night out?” and, “I thought you said she was a cardiologist, but then when we see her patient, he’s complaining about a broken leg.” That’s a huge help to me.

They’ll say, “Stop using that adverb. You’ve used it three times in 4,000 words.” I get a lot of editorial guidance and help when it comes to the actual execution of the sentences that I’m super grateful for. But I don’t get the notes that I get all the time in TV and film of like, “Can you make the protagonist more likable?”

John: Totally. Where are you at in your process? This book is coming out July 23rd. Everyone should buy it. Is the next book already done? Are you short story by short story? Where are you at in your work?

Simon: I used to do that. I used to basically, when I would finish a book, I would literally turn in a book and then the next day would start the next one. Now, I try really hard not to do that, because I find that especially my early books, I started to repeat myself, because I hadn’t allowed myself to live life in between the books. I would just be writing the same book again, but slightly worse. I don’t want to single books out. But I think the first half of my career, there are definitely a few where I’m like, I should’ve maybe waited a year before diving back into it.

What I’m doing now is the same thing I’ve done after the last few books. I just try to generate premises from reading. I read a lot about subjects that I’m interested in. I let myself just jot down premises that I think might be worth exploring. I’m not gonna pursue any of them for probably another six months or so.

John: You’re not a person who beats yourself up if you’re not sitting down generating 1,000 words per day.

Simon: No. I work a set number of hours a day, I would say. But sometimes my work is just sitting down for six hours and reading a book about zeppelins, because it’s been proven to me that that’s useful.

There was a yearlong period where I was just obsessed with pirates. I would just read endlessly about pirates, and to no end, really. Then one day I just got the idea for a story about two pirates, Captain Blackbones the Wicked, and Rotten Pete the Scoundrel. They find a stowaway on their pirate ship, and they have to decide whether or not to throw the stowaway overboard to the sharks or to feed her and take care of her. I was like, “Oh, this is a parenting story.” I ended up writing the story Learning the Ropes in my last book, New Teeth. I wrote that story a full year into my pirate obsession. There are a number of topics like that, where I’m like, someday I’m sure I will figure out. I will crack it. But you can’t really force it.

John: Simon, an absolute pleasure.

Simon: Thanks. Thanks for having me.

John: Thanks.

Links:

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