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Humor writers are a rare breed. Not everyone shares the same sensibilities, so when you read the work of someone who is not only on your comedic wavelength but makes you want to write better jokes, you feel lucky. When I first read Jen Spyra’s “To the Class of 2050” piece in the New Yorker, I felt lucky.
I immediately sought out her other work and was grateful to learn she was working on The Late Show With Stephen Colbert at the time. Though she has since left the show to pursue other writing, she hasn’t lost a step, comedically. That much is evident in her new, genre-hopping humor collection, Big Time, which tackles an extremely serious bridal body boot camp, a cringeworthy date with Sherlock Holmes, and an amnesiac enrolled in an elite boyfriend training program, to name a few. I spoke to Spyra about joke-to-plot ratio, writing for a late-night show, and knowing when to walk away. Our conversation has been edited and condensed for clarity.
Eric Farwell: You’ve had the experience of both being at the Onion, which is often a steppingstone to a late-night job, and The Late Show, which you left in 2019.
Jen Spyra: I hugely lucked out in getting in on the ground floor with The Late Show as we were conceiving it. And then the biggest stroke of luck was just that Stephen was the host, and I got to write for him. Stephen was already one of my comedy heroes from Strangers With Candy. I sparked to his sensibility early on. He has that glib, blithe darkness that really kills me, and he’s an adventurous performer. He’s a dream to write for, because he gives you a really big range to play with.
Before The Late Show and the Onion, what were the steps you took to break into comedy?
I didn’t even know about short form comedy writing until my senior year of college. I mean, I found out about McSweeney’s my senior year, and I was blown away by it because I had never read anything like it—these short, essentially pointless, evergreen comedy pieces. Finding that website was a revelation. But the road for me was pretty windy. After college, I lived in France for a year teaching English at a high school, but the whole time I was just dreaming about moving to Chicago to do improv—which, to my parents’ misery and confusion, is what I did. But then on the side, I was always writing short humor pieces. So, basically from 22 to 27, I’m doing improv, doing sketch, writing these short pieces—they’re not even stories yet, they’re just one- and two-pagers. And 27 is when I get hired at the Onion, which was the huge break, because that was the first time that my fantasy-job life merged with my real-money 9-to-5 life.
During this fellowship, are you learning how to write an Onion piece in terms of formatting and things like that? Is there a learning curve?
Oh, there’s a curve. At least, there was a huge learning curve for me. It’s a sink-or-swim six-month audition to get asked to be on the staff. In the beginning, I was messing up left and right. I remember one of the first articles I wrote was about some event in heaven, and I wrote “Heaven” instead of “The Heavens” in the dateline. Just a teeny mistake like that made me seem like a total rube. But the biggest thing I had to get right was the tone.
On any staff that already has an established editorial voice, the game is that you serve that voice, but then you also want to put that spit shine on it, and that’s your own unique perspective. It seems like writers who end up being assets on staffs and have fun at the same time are able to strike that balance. I wasn’t always able to strike it. Sometimes, especially at the Onion, at Colbert, I wasn’t exactly champing at the bit to write about that day’s big topical stories. But you’re being paid to do it. So that’s when the brute force comes into play, and just being a comedy draft horse.
What happens in those instances where you have to muscle through? What do you do when you don’t really feel it?
Luckily, you don’t have to be in a good mood to write topical comedy. It’s just about looking at a news story, isolating the data points in the story that are a little bit weird, a little bit off, and then writing hard jokes off those data points. Ultimately, it’s an analytical exercise, so if a story makes you angry or depresses you, that doesn’t necessarily get in the way of being able to write something funny about it.
At the same time, was pitching to the day’s tentpole stories my favorite part of the job? No, siree. At both gigs, I preferred coming up with evergreen pitches—less urgently topical, trend-based satirical pieces. Even when you have a banner day, and you land a pitch you’re really excited by, your favorite joke might get cut after rehearsal, and it hurts.
So then what were the signs for you that it was time to leave the show?
Writing a short story collection was always a dream of mine. So when I got the book deal with Random House, and then the deadline was looming, I realized I needed to focus on it full time. The thing is, with one of these late-night shows, you know, the money is great. You want that money to keep piling up, but at the same time, growing and scaring myself artistically, that’s also really important to me. The book was just so exciting and scary. I wanted to give everything I had to that.
What was the impetus for the new book?
The impetus really was the freedom that I tasted in teeny little bites when I submitted stuff to the New Yorker. I started getting things into the New Yorker pretty early on at Colbert—but keep in mind, that’s after years of rejection—so I always had this fun side game of writing that stuff. There are still rules, of course, when you’re writing for them—word count, for one thing—but it was definitely more freedom than I had at the Onion or Colbert, where the voices are so established and I’m kind of squishing my own voice into a preestablished groove. The artistic freedom of writing short fiction was totally intoxicating. It’s so exciting to get it in the real-life mag, because for one week you’re the king of New York, and you’re featured next to all these venerable writers. It’s like, sorry, Dexter Filkins, you have to slum it next to me this week.
Even though I loved writing for the Onion and Colbert, for someone like me with my, shall we say, particular tastes and my weird sensibility, there was a ceiling to what I could explore. It was just really exciting to think, what if I had no rules? What would that even look like? Because often at the Onion and Colbert, I was a writer that was reined in. I had the reputation of “Oh, don’t ask Jen if that’s too dark or too weird. She’s not going to say no [to the joke].”
What was the editorial process like for Big Time, considering you’re coming from a world where you’re used to getting notes from comedy writers or editors, not book editors?
The main headline here was I was shocked how little note giving there is. There’s almost no note giving. And I was used to being brutalized on a daily basis. As a late-night writer or Onion writer, you turn the script or draft in, and then it no longer belongs to you—it belongs to the machine, and so accordingly, it can be cut or changed in a million ways to serve its needs. As a staff writer, you’re simply a team member working towards the greater good.
But when you’re working on a book or a play—because it’s like this in theater too—you get the kid-glove treatment. It’s incredible. Your editor trusts you have a vision, and they want to serve that vision. I have never been in that position before. I was used to so much editing, and I don’t want to say interference, because I often agreed with my overlords and indeed appreciated their punch-ups. At first, I felt a little wobbly not getting hard notes. My editor’s edits and suggestions were subtle, but they were really, really helpful. Often, it had to do with maybe making a character more vulnerable. A note can be that overarching and amorphous, but then I was trusted to just sort of figure out how to fix it on my own.
Do you feel like writing short humor helped you to be good at matching the different genres in Big Time, or does it come from somewhere else?
First and foremost, I’m trying to think of a fun, juicy idea for a story. And genres are so fun to play with because they all have their own set of rules, so I already have some guideposts because if I know the rules, I can play with them and subvert them to tell a different story. But in terms of writing in the different voices, I think my ability to mimic them, to the extent that I pull it off, is based on my passion for the genre, my real, deep love for it and familiarity with it. Or, of course, you can just kinda fake that if you steep yourself in it. Like, I’m not obsessed with action thrillers, but I know enough tropes and enjoy them enough that I was able to pull off a parody of one in my story “The Boyfriend Identity.”
And in “Monster Goo,” it’s just Goosebumps. I was obsessed with Goosebumps as a kid. The books almost read like screenplays and, you know, all of the onomatopoeia and the really stupid, endless descriptions of outfits the characters were wearing. The seed for that was simply remembering those stories, and that the kids get into these supernatural scrapes. The adults are bystanders. They never have to turn to the adults for help. The kids fix it themselves. And then, because I’m an old now, I started identifying with the parents. And I was like, what if, you know, I had a son and the little dumbass ate monster goo and got huge and he couldn’t fix it? How would that impact my life? So I got teed myself up to write in the voice of a Goosebumps book, as I deconstructed the genre to tell a new story that I hope is entertaining and not just incredibly sad.
Do you feel like it’s the same engine driving all of your work? Is there an identifiable factor that makes a New Yorker piece tick, an Onion piece tick, these stories tick?
In terms of an engine—feeling passionately about what I’m writing about, which oftentimes can just mean being angry about something—that can give a piece an energy, a specificity, that helps distinguish it. But there’s also good old-fashioned pointers that, if you stick to them, elevate the writing. I mean, off the top of the dome, have your characters be in conflict. Keep the story moving. Raise the stakes. In terms of comedy, specificity is always key. And if you’re going to be talking about dark stuff, as I do in a lot of the stories, you have to maintain enough lightness, enough levity, so that it never is overwhelmingly dark and the reader can still have fun—which really has to do with timing, and knowing when to ease up and give the reader a break.
Do you start with a genre in mind, or do you have an idea and you’re like, “This kind of wrapping can work for the engine here in the story”?
Yeah, it’s not as analytical as “I have a story, and what would be the best vehicle?” First, I just have to be grabbed by something—maybe it’s an emotion that I’m feeling intensely at that time, like when I was getting ready for my wedding and I felt anxious about wasting so much time getting physically ready, i.e., getting hot—or it could be as simple as asking myself, “What’s a world I’d like to live in for a little while?”
One story that started that way was “1001 Nights,” which is my retelling of the Persian classic from Arabian Nights. It’s so atmospheric. I felt like it would be fun to write in that world. And it’s a story about storytelling. It’s about the challenge of keeping an audience coming back for more. As a writer, that self-awareness appeals to me. Inspiration rarely strikes in some exciting, dramatic, lightning-bolt way. Typically, an idea comes from just sitting with my laptop, and it’s blank and glowing, and maybe a deadline is looming. It’s no more romantic or sexy than that. It’s just brute force.
Was all of this helpful in figuring out how to write the novella in the collection, [also titled] “Big Time”?
Yes. I do think there was a reason that that was the final story I turned in. With “Big Time,” I told my editors a year before I wrote it that that was going to be the title story. I had this idea for a fish-out-of-water story about a 1940s-era actress who gets flung into the future and has to make it today. I can’t tell you how torturous it was to write. I can’t tell you how much it was sucking, how it was not working, until the last minute. That was the most terrifying part of writing it, because I’d talked this big game about it and essentially pitched it as a big chunk of the book. At first, the stories I was writing for this collection were around seven to 10 pages. Then I wrote a longer story that cracked the code for me, which was “Birthday Girl,” and that was maybe twentysome pages. “Big Time” is over a hundred, and I think I worked on it off and on for two years—I’d get frustrated and then write another story. And it started to feel like a piece of cake to write a 30-pager, because I was having such a rough time with the novella-length one. But I had this faith that it could be cracked. The aha moment there came when I realized how conversational it wanted to be.
It definitely paid off. Can you speak more about what makes the [1940s] era’s language so perfect for comedy?
For comedy writers, really any writers, film noir is a trove. The writing is so instructive, specifically for comedy writers, but also for anyone, because the similes are so sharp and unexpected. I think Raymond Chandler’s The Long Goodbye has a line like, “I belonged there like a pearl onion on a banana split.” I mean, it’s just a nice little provocative, accessible simile. I have always loved old Hollywood. The idea here was deconstructing a classic Hollywood-memoir rags-to-riches story but then also telling a real story that has that emotional backbone. It’s about a woman who is ruthlessly ambitious and thinks being “big time” (forgive me) is about being successful, and realizing that being “big time” is really about the magic of friendship and having at least one friendship that really matters to you. So first, I wanted to tell an old Hollywood story—but I also chose noir because I was excited to write these funny similes and metaphor, that you get to do when you’re working in that 1940s hard-boiled femme fatale voice.
When you don’t have such kinds of perfect pairings in the language, narrative, character, and comedy coming from that, do you find it hard to manage and make calls on that joke-to-narrative ratio?
That was always on my mind. Managing the pacing was a huge challenge. Coming from the world of the Onion and then The Late Show, I really did have to fight my instinct, which was to slam a gazillion jokes into it. Sometimes I would get nervous, because I’d be thinking, “Oh, we’ve gone too long without a joke. You’re boring them. You’re losing them.” I had to actually learn: “Oh, no, you’re letting the reader breathe right now. You need to do that.” I had to learn to put interstitial tissue, just world-building tissue, into stories. That was something that I didn’t do in writing at my other jobs. You can’t. Scripts and sketches are very bare-bones, and stage directions are the equivalent of that tissue that you find in fiction. But the stage directions are supposed to be incredibly spare. I had to teach myself to build out worlds. It’s new to me, but that was something where I was like, “Oh, this is how a short story is different from a sketch.” At first my instinct was, “That’s just fat. You’ve got to cut that out, and you’ve got to get to the next joke faster.” And then I realized, “Oh, the jokes cancel each other out if they come at you too fast.”
A lot of the work in the collection deals with bodies—a fiancée wanting a perfect body for her wedding, a prehistoric influencer who gets eaten by a tiger, a gigantic teenager, a millennial pig, or a time-traveling actor. Was this a conscious thing for you that you were focusing on, or did it just arise naturally in the material?
I mean, I never came at any of the stories with the intention of exploring bodily limitations. But, of course, as a human being on Mother Earth and a woman, I have so many body things that I am personally obsessed with. Punishing exercise is something that I’m interested in, that I have pursued in my own life. Being trapped in my body all the time is funny to me, and I’m constantly feeling limited by it and interested in feeling limited by it. I mean, in high school, I had scoliosis, and I wore a back brace for about a year. I think that helped give me an outsider perspective. In “Big Time,” the main character has a serious operation as a child for a freak reason—a similar thing happened to me as a teen, so I’ve had outsider body perspectives, and maybe that’s why it is something that I’m obsessed with.