Jessica Gross | Longreads | Oct. 2014 | 17 minutes (4,290 words)

By the time Simon Rich graduated from Harvard, where he served as president of the Harvard Lampoon, he had a two-book deal from Random House. Less than a decade later, the humorist has written four short story collections and two comic novels. He also spent four years writing for Saturday Night Live (he was the youngest writer SNL ever hired) and about two years at Pixar, and is now at work on a film and a television series.

Rich’s level of productivity, impressive as it is, takes a backseat to the quality of his humor writing. His stories are crystalline, eccentric, and universally hilarious. Many of the stories in his new collection, Spoiled Brats are built on an unusual premise, or told from a surprising angle. In “Animals,” a hamster narrates his wretched existence as a class pet at an elementary school. In “Gifted,” a mother insists that her son—born as a monster, with horns and a tail—is exceptional. And in “Distractions,” a writer believes the whole world is out to get him, and they really are.

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How old were you when you started actively, seriously writing?

Well, I always loved to write. As early as kindergarten, I plagiarized Roald Dahl stories that I would try to pass off as my own. But I think it sort of shifted around when I was 17. That’s when I started writing every single day, whether or not I had an idea. Until then, I would only sit down and write a story if one occurred to me, and then I started to wake up every single day and write for a few hours whether or not I had anything worthwhile to say.

What was the impetus for doing that?

It was because I wanted to write a novel. I wrote a novel that I finished the summer after I graduated from high school—it was a terrible, terrible novel—but I knew I was going off to college and I assumed I would be too busy to write a whole book, so I decided I would finish it before I got to college. But a novel has a lot of pages, so I knew I would have to work every single day. When the summer was over, I had failed in writing a good novel, but I had succeeded in learning how to be a writer.

And you’ve just kept up that habit ever since?

Yeah, and gradually, over the course of years and years, the writing got a little bit better.

Do you ever have a day when you sit down to write and it’s just not happening?

I always find something to write about. I mean, you always have some emotion inside of yourself. Sometimes the only emotion you feel is shame or disgust or embarrassment or whatever—it’s not always the sexiest emotion—but as a living, breathing person, you always have something going on inside of your brain and inside of your heart. There’s always something you can write about.

Your stories are so richly imaginative and kind of outlandish. Do you find that you’re the kind of person who daydreams a lot? Do these kinds of scenarios occur to you in your non-writing life, or is it a very disciplined thing where you’re sitting down and thinking, “What’s a scenario that would embody this emotion”?

I occasionally will suddenly have an idea out of nowhere—in the stereotypical Hollywood way, inspiration will strike—but that probably accounts for five or 10 percent of all of my published work. The rest is the result of brute force.

So what does that mean, brute force? When you’re sitting there, how do you actually go about brainstorming something that is so far out?

It’s all about finding the right angle, right? Because none of the stories I tell are particularly original, and none of the themes I write about are new, and certainly, hopefully, none of the emotions I’m writing about are unique. So it’s just about coming up with an original creative angle. So with “Sell Out,” I don’t think I’m the first person to wonder what it would be like to meet their ancestors. I mean, there’s hundreds of works of art about it—everything from Back to the Future to Time and Again deals with those issues—so it was just about trial by error, systematically telling the story in every conceivable way until I found one that felt fresh and interesting and honest. Or the story, “Unprotected,” in my last book—I mean, how old of a story can you tell? A teenage boy who wants to lose his virginity: It’s the premise behind dozens of popular films. So it was just about, what’s an original, creative and visceral way to tell this old story of a teenage boy trying to get laid?

There are two Simon Rich characters in Spoiled Brats—a kid in “Animals,” and a late-twenties man in “Sell Out”—and they’re both very unlikeable. How great of a distortion is each?

I would say that the book is embarrassingly autobiographical. I think those negative portrayals of Simon Rich are, I would say, shamefully accurate. [Laughs.]

So the kid who appears in “Animals” is kind of a chubby monster—

Yeah, he’s referred to as a monster by the hero of the story, the class hamster, and I think the hamster calls it like he sees it. I don’t think any of his opinions of Simon Rich are off-base.

Earlier stories in which you’ve had a Simon Rich character tend to be told in first person. Why have you moved into a third-person perspective for these?

It’s become something of a postmodern trope to make yourself a character in your books. It’s been done more and more with every passing decade, from Martin Amis to Jonathan Safran Foer. I always thought it would be more fun to make myself the villain than the hero. It just seemed like a more creatively interesting idea. And if you’ve made yourself the villain, it’s more fun to write about yourself in the third person, because then you can really have at it.

How much of these harsh portrayals was an attempt to draw the reader in with an appealing level of self-deprecation, and how much comes from some real self-loathing or embarrassment or guilt?

This is definitely, by far, the most self-loathing book I’ve ever written. I mean, the book is called Spoiled Brats, and I’m the main villain. But I’m hopeful that some of the readers will relate to the characters in the stories and see something of themselves in them. I mean, the character of Simon Rich in the book is extremely narcissistic and self-absorbed and egomaniacal, and I think everybody has a little bit of that in them.

In “Animals,” it’s Simon Rich’s turn to take care of the class hamster, and he blows it off. Did you have pets as a kid?

Yeah, I had classroom pets, hamsters, and I treated them terribly. It was my job to feed them occasionally, and I almost always forgot. My focus at the age of seven and eight was really just to watch television and sitcoms and then repeat the catchphrases as loudly as I possibly could. That was the fundamental goal of my existence for that period of my life.

In the story, Simon’s choice phrase is “Whatchu talkin’ ‘bout, Willis?” Was that yours, too?

“Whatchu talkin’ ‘bout, Willis?” was up there, but I remember quoting The Simpsons ad nauseum, and everything from Harry and the Hendersons to The Hogan Family. I quoted everything that was in that box. The magical box.

The kids in Simon’s class in the story seem to really take a shine to this habit—did you get that reaction?

You know, it’s hard to know, because I had such little self-awareness at that age. I think at the time I probably thought that everything I was saying was hilarious.

At what age did you start to view that behavior as embarrassing?

I would say my late-20s. [Laughs.]

Your writing has very surprising subversions that come fast and often, which lend a lot of comedy, but I feel like the humor is also often tied to linguistic details. So, for example, in that story, Simon is crying after the hero, the hamster, bites him. The whole setup is great, but the part that made me cackle was the hamster’s line, in remembering his moment of glory: “I smiled proudly, thinking of this scene.” The formality of expression—

Yeah, it was very important to me to give the hamster high status, because he’s so downtrodden and put-upon. It’s just a basic comedy rule: If you’re going to strip somebody of his dignity, you want him to start off as high-status as possible. Not to get too technical about it—I mean, dissecting comedy is always the most boring thing in the world. There’s no better way to ruin comedy than to talk about it. But yeah, if you’re going to throw a pie in someone’s face, you want it to be a man in a tuxedo, not a homeless person. So for that reason it was important, comedically, to make the hamster formal, articulate, eloquent and high-status, and so I gave him verbiage that I thought would bolster that.

I know it’s a cliché that deconstructing a joke ruins it, but to me, the way comedy works is so mysterious, and I love having it explained. Are you saying that it ruins the joke for the person hearing it, or do you personally prefer not to be deconstructing comedy in this way?

I don’t mind talking about it, I just feel bad for people who have to listen. But obviously, like all comedy nerds, I’m a student of comedy, I grew up obsessing over joke structure and trying to figure out why the things that made me laugh were making me laugh. In the writer’s room at my show we spend hours and hours deconstructing jokes and gags and premises, trying to make them work more efficiently. So it’s like anything else—it’s like cooking or doing magic tricks or playing baseball: there’s a lot of technical thought that goes into the construction, and it’s very learnable. Anyone can learn these tricks, I’m convinced.

I’m a student of comedy, I grew up obsessing over joke structure and trying to figure out why the things that made me laugh were making me laugh. In the writer’s room at my show we spend hours and hours deconstructing jokes and gags and premises, trying to make them work more efficiently.

It’s interesting that it comes down to such logical components, when the experience of hearing or reading comedy doesn’t feel that way at all.

Yeah, there’s a technical aspect to all creative pursuits. Even the most experimental abstract expressionists have to stretch a canvas, right? I mean, there’s a lot of technical busywork that goes into the construction of any creative medium. But it’s learnable. It’s not that hard. I’ve got about five or ten rules of thumb that I keep in my brain as I’m writing. But then also you end up breaking these rules, and sometimes a joke will work because it’s subverting another joke form. Like the piece in this book, “Guy Walks into a Bar,” is basically just one big anti-joke that subverts one of the oldest joke structures in the world.

So what are the five to ten rules you keep in mind?

These are some real basic ones, but you always want to end a joke on the word that will elicit laughter. You want to make—and this is just for me, a lot of people will disagree—I always try to make things as economical as possible. I always try to make the turn sudden. I try not to shift a scene gradually, I try to shift a scene dramatically. Clarity is extremely important—just like with a magic trick, if a person watching has been lost during the setup, they’re not going to understand the payoff and they’re not going to marvel at it.

There’s a lot of societal critique in some of these stories, like “Gifted,” which uses a wealthy mom’s relationship with her son—whom she treats as a uniquely gifted child, although he is an actual, literal monster—to skewer class privilege and modern parenting. How much of that is a byproduct of the funny story you want to tell and how much is deliberate critique?

You know, when I’m writing comedy, I try not to come at it from a political place. I’ve found that whenever I try to get a point across through a work of fiction, the story ends up being didactic, stilted and propagandistic. So when I write a story, the main thing I’m thinking about is, will it be emotionally visceral? Will it grab the reader? Will it make them interested in the characters and make them want to turn the page? That’s the main thing I’m thinking about, more so, even, than whether or not it’s going to be funny. So with “Gifted”—I mean, it’s not a new premise, it’s essentially Rosemary’s Baby—but I thought that the naïveté and ignorance of the speaker, the mother, would lend itself to some suspense and also some good gags.


I was noticing your language again in this story, particularly this, about her monster son Ben: “Once, during a Spanish midterm, he escaped into the Hudson Valley woods and lived as a beast for several months.” Again, the premise is really funny, but it’s that phrase, “lived as a beast,” that really got me.

Yeah, “beast” is a great word, right? Packs a lot of information into a single syllable. I really like the word “beast,” and I use it a lot. Often, with a book, I have certain favorite words that I use over and over again because they always make me laugh, and then during the copyediting phase I always get a list from my editor of words that I’ve drastically overused, pleading with me to use synonyms. I do, up to a point, but you always find the word “beast” at least a dozen times in each book. You’ll always find “nightmare” and “horrible” and “sigh.”


People are perpetually sighing in all of my books, because they’re constantly exasperated by these terrible situations that I’ve thrown at them.

People are perpetually sighing in all of my books, because they’re constantly exasperated by these terrible situations that I’ve thrown at them.

Were you surprised by any of the words you were told you’d overused in this book?

“Williamsburg.” I was surprised how many of those popped up.

So the centerpiece of this book is “Sell Out,” which I originally read on The New Yorker’s website [see part one of four here], in which a 27-year-old Brooklyn writer named Simon Rich meets his great-great-grandfather, an immigrant who fell into a pickle barrel a century ago and was preserved in brine at exactly Simon’s age. What was the very first bit of this story that you got down on paper?

At least since college, I’ve been thinking and writing about the kinds of conversations I might have with my ancestors if they saw how frivolous and privileged my life was. And the shame and guilt packed into those conversations always made me laugh. It took me a really long time to figure out how to construct a story that would allow for those interactions to occur, and I guess I was 27 when I really started diving in and trying to write my ancestors’ story in earnest for the first time. It took me five or six tries to really find the right angle, because with all comedy writing—all writing, I assume—you’re constantly making choices: first person, third person, second person? Who’s talking, why are they talking, who are they talking to? You’re constantly making all of these decisions and having to be self-aware about why you’re making them.

There was a version of “Sell Out” told from my perspective. There were two versions that weren’t about me specifically, just about generic hipsters being visited by their ancestors. And ultimately I had to step back and ask myself, “What is making you laugh about this? What is compelling you to write this, what emotion is driving this?” And it really was guilt and shame. And so I thought, if that’s what this is really about, then I need to have that ancestor looking directly at me. I need to give him the power and give him the agency. So then I started writing scenes with him just watching me, describing me, and I got a lot of comedy out of that. But then the larger themes started popping into my brain—the immigrant experience and the Occupy movement and issues of class and privilege and the American dream and religion and humility versus pride—and the plot gradually presented itself. And then it went through a bunch of other drafts; the plot kept changing. There was a time when I was going to do it as a full novel, but then I decided that parts of it were too bloated and I didn’t really want it to be that long, so I cut a bunch of it. It was a long-ish process. It’s only about 75 pages, but it probably took me as long to write it as it normally takes me to write a full novel.

How many pages do you think you wrote that didn’t end up in the final piece?

Oh, hundreds. But that’s typical of me. I throw out most of what I write. But percentage-wise, what I kept for “Sell Out” was definitely the lowest.

How do you approach writing a collection? Do you start writing one-offs for The New Yorker and then think about what kinds of pieces would fit around them to form a thematically driven collection? Or do you just decide to put the stories you’ve written into a collection afterward and see what theme emerges?

I find it impossible to write about anything but what I’m interested in at the moment, and my interests and passions tend to shift from year to year, so that sort of naturally lends itself to collection writing. When I was 25, 26, the only thing on my brain was dating, and that’s why I wrote all those love stories which became The Last Girlfriend on Earth. And then for a year or two I was obsessed with class and privilege and turning 30, and Spoiled Brats is the result of that.

There’s this Fresh Air interview with Carrie Brownstein and Fred Armisen in which Brownstein says that she very much embodies the Portlanders they spoof in Portlandia, that she’s not above their behavior or making fun of them. So what is your life like in Brooklyn—do you act like the hipsters you poke fun at in your writing? Do you go to the craft beer bars, do you take joy in the lifestyle?

Oh, yeah, completely. All of that stuff. I’m a complete, full, bourgeois yuppie, unequivocally. If there is a hipster on earth, it’s probably me. I’m certainly as revolting and privileged and narcissistic as any of the hipsters described in my book, if not more so. I mean, there’s nobody worse than me.

I’m a complete, full, bourgeois yuppie, unequivocally. If there is a hipster on earth, it’s probably me. I’m certainly as revolting and privileged and narcissistic as any of the hipsters described in my book, if not more so. I mean, there’s nobody worse than me.

[Laughs.] I’m getting that sense. So, to go back in time a little bit: you grew up in New York City, in the East 50s; your parents were divorced and you and your older brother spent most of your time at your mother’s. Can you describe what the dynamic was like in your house?

It was great. I had a great family, really supportive, wonderful parents and step-parents and wonderful older brother, great teachers, really lucky in every single possible respect.

That’s … wonderful.

[Laughs.] Yeah, I really hit the jackpot.

You read a lot of Roald Dahl as a kid? Who else?

Yeah, a ton of Roald Dahl. I was obsessed with Mad Magazine, I was obsessed with sitcoms—in particular, The Simpsons, but also everything on Nick at Night, from I Love Lucy to Dick Van Dyke and The Mary Tyler Moore Show. I raided my older brother’s bookshelf and through his library found writers like Philip Roth and T.C. Boyle and Kurt Vonnegut. By the time I got to high school, I was really obsessed with premise writers of all kinds, not just comedy writers like Douglas Adams and Joe Heller but also people like Shirley Jackson and Stephen King.

We get a sense in “Animals” of what you were like as a kid, and in “Sell Out” of what you were like in your late 20s. What were you like in high school?

Super-pretentious, showing off a lot, kind of self-serious, insufferable. But fast, really fast. I ran the mile and I was really good at it. So I was at least quick on my feet. But in general a total nightmare.

How fast could you run a mile?


Are you serious?

Yeah—which is, by the way, not great for most parts of the United States, but in my insulated private school community, I was fast. But we would race against large public schools and just get our asses kicked.

Do you still run?

Yeah, I run every day. Six miles.

After you graduated from college, you worked for Saturday Night Live for four years. The schedule there is notoriously punishing. Was it difficult for you, or were you just so creatively stimulated and excited to be there that it didn’t matter?

Yeah, I was just grateful to be there. Obviously, it’s a lot of long hours—you have to stay up all night once or twice a week—but you do get the entire summers off, so it’s not as grueling as it sounds. You’re certainly very tired by the time the show starts on Saturday, but you can also spend July and August writing a novel in your bedroom, so there are definitely harder jobs. I think it would be a lot harder to be a staff writer on a sitcom and work 48 weeks a year, nine to five, in a room. I think that would be way more grueling, personally.

You’re writing a film based on “Sell Out” with Seth Rogen and Evan Goldberg. How’d you decide to work with them?

I’ve been fans of theirs for a really long time, and I’ve worked with them before. I actually wrote Seth Rogen’s first monologue on SNL. I think they’re really smart, and “Sell Out” is so tonally similar to a lot of the stuff they’re doing these days, so it just seemed like a good fit. I just trust them.

What can you tell me about the ways in which the film will differ from the story?

That’s always in flux—it shifts from draft to draft. But there’s a lot of stuff that works best on the page and there’s a lot of stuff that works best on the screen, and when you adapt from one medium to another you have to really use the medium, and think about the medium before you think about the material. That’s definitely one of the things I learned at Pixar. The most famous and beautiful scenes in Pixar history have no dialogue, and the reason why is because they’re an animation company. So they’re using the medium effectively. Whereas if you were working on a radio show it’d be a different story. So you have to think medium first.

I imagine that was a learning experience on SNL, too, coming in as a writer and then having to translate from a script to a staged sketch.

The biggest learning curve for me was going from a magazine and book writer to being a sketch writer. That was the hardest thing, because writing for performers is so different from writing for the page.

You’re working on a number of other film and television projects right now, too—there’s a film based on your novel Elliot Allagash, and a TV series based on The Last Girlfriend on Earth called Man Seeking Woman. Am I missing anything?

Yeah, but you don’t want to be the guy who—

No, tell me!

No, no, as a screenwriter, you never want to be the guy who breaks news. It’s just, it’s unfair.

Oh, I thought you meant you didn’t want to be the guy rattling off your list of projects.

Oh, no, are you crazy? I’d love to brag about every aspect of my life. This is what I live for. If it were up to me, I’d be reading you my shopping list.

Edited by Mike Dang. Photo Credit: Melissa Fuller.