Writer Simon Rich wears many hats. He rarely sports them outside where anyone would notice, but from what I understand, at home, he’s sporting no less than eight to 12 hats.
Rich also does a bit of everything in the entertainment industry. Emerging from the time-honored comedic pipeline of the Harvard Lampoon, the writer found himself with a two-book deal right out of college, then landed a job at Saturday Night Live at the age of 24. With a taste for the absurd and a tough of magical realism, his oddball sketches quickly became favorites of Comedy People Who Might Corner You at a Bar in Brooklyn. At SNL he’d pick up a few Emmys before jumping to a stint at Pixar, creating Men Seeking Women for FX and Miracle Workers for TBS, and adapting one of his own stories into the Seth Rogen vehicle An American Pickle.
But every few years, Rich returns to his original, formal stomping ground: the short story. Rich is the author of several collections, including Ant Farm, Spoiled Brats, The Last Girlfriend on Earth, and Hits & Misses. His latest, New Teeth, finds the author once again dreaming big and dreaming weird, imagining everything from a woman raised by wolves reuniting with her family for the holidays and a wayward half-man, half-ape superhero finding his way in the world. With the book now out on shelves, Polygon spoke to Rich about the never-ending quest of making the funny. (Unfortunately, the whole hat thing did not come up.)
Let’s start with the obvious first question: Are you obsessed with Beauty and the Beast? There’s a story in the book that sounds very autobiographical that would lead me to believe you are obsessed with Beauty and the Beast.
Simon Rich: I’ve become completely obsessed with the live-action version of Beauty and the Beast, and I had no choice but to become obsessed with it because my daughter was, so I had to truly force myself to learn how to love that film.
But you also wrote a Beauty and the Beast sketch at Saturday Night Live.
That’s true! I wrote a sketch for Gerard Butler. I wrote it with Marika [Sawyer] and [John] Mulaney, like I wrote most sketches. But, you know what, when I was writing the short story, I kind of forgot about that. Because now, when I hear Beauty and the Beast, I think only of the live-action Josh Gad version.
When you embark on a short story collection like this, do you block off your schedule and say, “I will create comedy today,” or do the stories spring up from the downtime between film and TV projects?
It’s very much the latter. It kind of happens by chance. I don’t sit down and write with a single theme in mind. I just write whatever short stories I think are going to be the most interesting, the funniest, and hopefully the most emotionally honest. And I always end up writing stories that are very autobiographical even though, on a literal level, they’re completely insane and have absolutely nothing to do with my day to day life.
What’s the oldest story in the book?
The oldest story in the book is “Revolution,” which ended up being the basis for the second season of Miracle Worker, [Dark Ages]. That’s a season of TV that came out before the short story was published.
You George R.R. Martin’d yourself.
Exactly. Although there was a version that I put on my BBC Radio show that predated the series. But yeah, this is the first time this one is in print anywhere. The most recent story I think is “Clobbo,” [a story about a half-man, half-ape superhero]. I wrote most of the book during the pandemic.
Was the book shaped by pandemic experiences?
I’ve always tried to not write topical comedy because I’m trying to write from a more emotional place and I always get worried when I’m writing a book that if I write something too topical, that by the time the book comes out, it’ll be completely irrelevant. But I think when you’re going through an undeniably extreme moment in global history, it can’t help but bleed into your work a little. Some of the stories were definitely colored by the pandemic. Like the story “Everyday Parenting Tips” [which is written as a guide for parents who need to explain a global monster apocalypse to their children]. Which is impossible. So how do you calm a child down when you yourself are completely freaking out?
Do you enjoy the solitary nature of writing? Based on your work on SNL and sitcoms, you seem to thrive with collaboration, but short story writing isn’t that.
I absolutely love writers room and, and I loved my seasons running sitcoms. I did three seasons of a show called Man Seeking Woman and then I ran Miracle Workers for the first two seasons. Although I didn’t run this season that’s [out now]. I just didn’t have time. I just didn’t have time to do it all. Also I wasn’t too excited about going on set during the pandemic. With a couple of little kids, or a kid on the way at the time, it was about not wanting to run a show during the pandemic and focus on other projects. You have to make some hard decisions. I really loved running that show, but part of the job is that sometimes you have to prioritize, especially when you have a family.
But yeah, I love about writing short stories because you can be way more emotionally specific. You have total control over what appears on the page and even when you’re directing a movie or running a TV show, you’re never going to have as much control over the final product because it’s intrinsically collaborative. Sometimes you end up with an episode of TV or a film that is different than what you originally envisioned, but in a good way because people have added cool things that would not have occurred to you. I love that about TV and film. I love being surprised by some of the choices the actors make or watching a joke in the final cut that’s brilliant, but something that I never would have written by myself. But it’s never as personal as fiction. That’s why I always return to it. Every couple of years, I always sit down and write another book because it’s the most authentic way to write, for me.
Do you miss getting the laugh when you write a book?
So bad. So much. It’s so tough because I can never really tell if something’s working. Luckily, what I do is I focus group the short stories. I send them out to a lot of people, and I ask people what they think. I always generate way more stories than actually appear in the book and I cut most of them.
Are there laughs that stick with you? Do you have a memory of a joke that killed? Or maybe a joke that played to dead silence?
The worst silences were always on Wednesday because that’s when we do the table read. If something is truly terrible, it will usually play to silence on Wednesday and then luckily, nobody will ever speak of it again. By the time it’s playing on Saturday, you know it must be at least OK. You’ll get a couple of chuckles. I’ve certainly wrote sketches on Wednesday that played to absolute silence without a single laugh. But Paula Pell always laughed because she was a nice person. If it was truly terrible, she would give a pity laugh. So I’ve put most of the sketches out of my mind because they’re too horrific.
But one sketch that I wrote that played to total silence was a commercial parody. The idea was a life jacket commercial and the demographic they were trying to reach was drowning people. People who are watching this commercial and are currently drowning. The joke was that they could basically charge whatever they wanted because you’re drowning.
Right. They need a life jacket. Because they’re drowning.
They really need a life jacket. I remember the narration was like, “Are you a person currently drowning? We sell life jackets. They’re not that great but what are you going to do about it?” Empty silence. And then a sweet, benevolent chuckle from Paula Pell.
Many of your stories evolve into TV and film projects, and even SNL sketches. Even when you publish them, do they feel like the beginning of that story’s lifespan in your head?
I hope they feel self-contained and polished. I really love the short story form, specifically. A lot of my favorite writers are short story writers primarily, like TC Boyle and Shirley Jackson. Stephen King, who’s better known for his novels, which are great, but I greatly prefer his short stories. Stanley Elkin is another one. I really love short stories and I’ve spent years trying to really hone them. What I love about writing short stories is that you can take a really big swing that wouldn’t necessarily be sustainable in a novel. You can write in a very unusual voice, you can pick a strange format, and you can take a big plot risk that would maybe be off-putting if you were to try to sustain it for hundreds of pages. But in a 15-page story, you can get away with it. Like, “Everyday Parenting Tips”: I think the [guide] style and structure would probably get annoying after 300 pages. In five pages, a reader will hopefully go with it.
One story in the new book is a big pirate adventure with a wacky soul. Do any of your ideas start as imagined blockbuster TV or movies that you know could never get made?
Whenever I have an idea that I believe in, I always write it as fiction. Always. I never pitch it to TV or film and I never have. I was writing short stories before I became a writer for SNL. My first book was called Ant Farm and it was published in 2007. I started writing for SNL pretty soon after that. Growing up reading Roald Dahl and Philip Roth and The Onion, I always thought of print first, and TV and film is something I fell into. So I still think in terms of words on the page more than anything else. What I love about writing is I can sit down and do it every day and not have to ask for permission. I don’t need to pitch my ideas to anybody as a prose writer. I can just sit down at my computer and see if it works. I love that freedom. It’s really exhilarating. I can write a pirate story and not have to ask for a budget to send a crew to Malta.
You mentioned Roald Dahl, and I know you’ve wound up working with Paddington director Paul King on both an adaptation of “Everyday Parenting Tips” and his upcoming Willy Wonka prequel movie. Is that a bit of a dream come true as a Dahl buff?
I can’t even talk about that, I can’t talk about any movie crap, it sucks! But yes, I’m an obsessive Roald Dahl fan. His stories were unbelievably instructive for me, and his pieces for Playboy and the New Yorker. I used to reread them over and over again. I couldn’t believe how transportive they were, how specific they were, how funny they were, and how surprising the endings were. My whole life, I’ve been trying to write short stories that hopefully can be as entertaining and engrossing as some of the ones that Roald Dahl did. He’s probably my favorite short story writer.