As the youngest writer ever hired at Saturday Night Live, Simon Rich achieved his biggest dreams ridiculously early in life. Everything that’s followed, including a stint at Pixar writing Inside Out, running his own shows at FX and TBS, and turning his multi-part New Yorker story “Sell Out” into the movie An American Pickle starring two Seth Rogens, has been beyond his wildest imagination.
And for him, that’s really saying something.
On this week’s episode of The Last Laugh podcast, Rich reads an excerpt from his latest short story collection New Teeth and reflects on his incredibly prolific career as the most ambitious comedy writer in the game. Plus, hear stories about what it was like to guest-write an episode of The Simpsons, the rejected sketch he pitched to LeBron James on his first-ever SNL episode, and tackling Willy Wonka’s origin story in the upcoming prequel starring Timothée Chalamet.
When Rich, who is the son of columnist Frank Rich, first started writing his unique brand of high-concept humorous fiction in college and into his twenties, most of his stories revolved around dating. Now that he’s married with two small kids, he spends a lot of time imagining what the adult world must look like through his children’s eyes.
“I always end up writing about whatever I’m emotionally going through,” he tells me. “So, it would make sense that my stories would be consumed by parenting. Because obviously that’s just where my head is at these days and what I want to focus on as a writer.”
It’s been just about 14 years since Rich joined the writing staff at SNL straight out of college, an experience he now says was “definitely scary” but also “thrilling.” Once you’re there, he says, “It’s really meritocratic. I never felt like, ‘Oh, I’m so young, you’re not going to listen to me.’ Because the way it works is, the sketches go up in front of people and they have no idea who wrote it and then they’re picked or not based on the audience reaction.” He says he never worried about the “politics” of whether Lorne Michaels liked him “because Lorne doesn’t know who you are when you’re a first-year writer, he’s worried about much bigger things.”
At SNL, he would constantly be pitching ideas that were way too elaborate to work within the confines of a live television show. He recalls going to then-head writer Seth Meyers and saying, “Here’s a bunch of premises. Which of these do you think have the best shot of getting on TV?” Meyers would reply, “Well, certainly not these eight, but maybe this ninth one.”
He still returns to SNL every time his old writing partner John Mulaney hosts the show. “It’s the best,” he says. “Everyone else is so tired. They’ve been doing SNL for months and you just walk right in fresh.”
Rich slowly figured out how to scale back his comedic vision during his four years at SNL, but by the time he got the opportunity to create his own scripted series based on his writing—Man Seeking Woman and then Miracle Workers—he decided to go for broke. “I basically forgot everything that I had learned and was just like, let’s go for it, who cares? Screw it!” he says. “I’m attracted to big swings. I always feel like it’s just more fun to have a spaceship land or have an animal talk or set something on fire.”
But if the characters he writes have one thing in common, it’s their fundamental lack of knowledge about the world around them. “From Homer Simpson to WALL-E, I love characters that are wildly misinformed, naive, confused,” Rich explains. “Those are the characters that I try to write about.”
“So, in New Teeth, an illiterate pirate starts off the tale,” he continues. “And then it’s a laser disc machine who is gradually becoming aware of his obsolescence. There’s a baby detective, there’s a fading mutant half monkey-half man superhero who is trying to figure out what to do now that there are no aliens for him to kill and smash anymore. There’s all these characters that are really just trying to make sense of a world that the reader already knows. And weirdly what happens, I find, is when you write from a naive perspective, you can sometimes be more emotionally raw than you can when the characters are super witty and smart.”
Next up, Rich is adapting his pandemic-inspired story “Everyday Parenting Tips” into a film starring Ryan Reynolds and working behind the scenes on Timothée Chalamet’s Wonka prequel. As both a “lifelong Roald Dahl fan” and a Jew, he tells me that he has somehow managed to see past his favorite author’s infamous antisemitism.
“That’s always a rough day in the life of a Jewish reader,” he says. “But yeah, I mean I’m able to overlook it. I’m always like, ‘Eh, he would have liked me though.’ We would have had a couple of drinks and he’d be like, ‘You know what, Jew? You’re alright. You’re one of the good ones.’”
Listen to the episode now and subscribe to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts and be the first to hear new episodes when they are released every Tuesday.
