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Former ‘Late Show’ Writer Jen Spyra Takes on Hollywood, Culture Tropes in Debut Story Collection


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Jen Spyra is no stranger to delivering comedy with a punch.

For three years, Spyra worked as a senior writer for The Onion, where she also headed the editorial video department as a writer, director and producer. Then she joined The Late Show with Stephen Colbert where she served as a staff writer for four seasons, writing topical political sketches and monologues (fun fact: Spyra’s voice can also be heard as the announcer for the CBS late-night show). While working at The Late Show, Spyra found herself writing short stories in her own time where she could find creative freedom and find her singular voice outside of her work. Soon she was inspired to write a book, and now Spyra is ready to debut her work to readers with her first story collection, Big Time (Random House), releasing March 16. 

“I loved writing on my own when it was on my own time [and] stuff that I was the final arbiter for,” Spyra tells The Hollywood Reporter. “This was my first time being completely free, no rules, unchained. And the more I worked on it alone, the more I really enjoyed being my own artistic boss.”

In her satirical story collection, Spyra pens fun, wacky tales with relatable characters (readers meet a bride desperate to get in shape for her wedding and a friend known to become a birthday monster) to fantastical characters such as a snowman who is more likely to become best friends with Billy Bob Thornton’s Bad Santa than beloved Frosty.

In the collection’s eponymous story “Big Time,” Spyra transports readers to the 1940s, where a starlet magically finds herself in modern-day Hollywood and yearns for success — the only issue is she’s unwoke. Then readers can even follow some famous faces including Jane Fonda, Gloria Steinem, Hillary Clinton, Taylor Swift and Selena Gomez, to name a few, as they gather for a secret meeting that has some dark twists and turns and will leave readers wondering, “Can this secret meeting be a real thing?” “They were the Most Powerful Women on Earth, united in the ancient cause of female world domination,” Spyra writes.

Though all comical stories, beneath the surface Spyra goes beyond the parody as she cleverly takes on topics from Hollywood and woke culture to white women, the wedding industrial complex and influencer culture. As Colbert writes in the book’s foreword, “Many of these stories feel warm and familiar, almost comfort food, but inside the burrito of this book there is a small dusting of broken glass — sparkling prettily but stinging.”

Ahead of the release of her debut collection, Spyra spoke to THR about writing her first book and how to write the perfect satire.

When did you decide you wanted to write a book and what you wanted to write?

I was always writing these short stories that were kind of my release valve. I got the idea for this collection while I was working at Colbert. I started writing these short humor pieces for The New Yorker and it was just so fun. When you’re on staff — for me, I’ve only been in two rooms at The Onion and [The Late Show‘s] Colbert — the challenge is serving the editorial voice of whatever show or publication you’re working for. There wasn’t a lot of gymnastics in terms of writing stuff that worked for the show that I also thought was funny, but I loved writing on my own when it was on my own time [and] stuff that I was the final arbiter for. That was really intoxicating; the freedom to kind of fully pursue my comedic sensibility and actually figure out what that was outside of these established comedy institutions. This was my first time being completely free, no rules, unchained. The more I worked on it alone, the more I really enjoyed being my own artistic boss.

Now having the creative freedom to explore your comedic voice through writing, what were the challenges, if any, that you faced during the writing process for this? 

The first challenge was simply breaking out of the mold that I really had sort of created for myself, which was writing short, 800- to 900-[word], one-page pieces for The New Yorker. I know how you keep up and how you heighten within a short piece, but it was a challenge to figure out how to keep the stakes high and keep a story going and sustain that over many more pages. From being someone who was a sketch writer for a late-night show, there was no interstitial tissue ever in anything you wrote. It was just like, “joke, joke, joke.” So getting to slow down and describe a character and take time in those moments when you really just need to give the reader a breather, those are things that don’t factor into TV sketch writing. Those were new things that were fun to figure out.

There are 14 short stories featured in this collection. How many did you originally write and how was it decided which stories would ultimately make the cut to be included?

We just cut a few stories. Some of the stories ended up being really emotionally hefty. Even though there’s comedy in all of them, some of them ended up not necessarily ending on a comedic note. It was my editor’s smart idea to shave off a couple of the stories that kind of didn’t really go with the flavor of the collection. When I write stories, I don’t work on just one. I’d probably work on three at a time. As I reach a wall with one and get incredibly frustrated, I will then go work on another one. The last story that I wrote was the title story “Big Time” and that’s a real big boy. As I was getting so frustrated, going through different drafts and not getting it right, I wrote a different story that’s also a kind of long one called “Birthday Girl.” I wrote other stories and I wrote stories just out of my desperation.

Can you talk a little bit about the overall process of creating these stories and these narratives?

I naturally wrote about areas and worlds that I’m obsessed with, either because I know them really well because I’m in them or I’m just fascinated by them. So the stuff that I know [included] influencer culture, showbiz culture and then I am fascinated by Old Hollywood. [Also] personal experiences with the wedding industrial complex, millennials, white women. Then other stuff was the childhood obsessions that still knock around in my brain that I sometimes end up just liking to fold into my writing [such as] The World of Beatrix Potter and Monster Zoo. Even though these stories are silly and fantastical and kind of nuts, a lot of them do come from personal experiences that I think are pretty relatable. “Bridal Body” is about a woman who puts herself through hell to get ready for her wedding day and that was totally personal. I fell into that trap and that was me. As I was writing it I just started to think, “What extremes could this be taken to?” As I kind of imagined that, that story took shape.

There’s a noteworthy story called “The Secret Meeting of the Woman’s Club” which features an array of famous faces from Jane Fonda to Hillary Clinton. Can you talk about writing that story and just deciding who you wanted to include? 

That story started off as a sketch that I wrote for The Late Show right before the 2016 election. We were sure Hillary [Clinton] was gonna win. So the original version of this story was a sketch where all of these important women were meeting and they had crossed off the presidency from the list of their goals and now they were going to focus on dumber, sillier goals. But when the election went the other way, the sketch was DOA because the mood nationally felt so dire and it felt like there was nothing really to make fun of. And [also] women’s second-class status felt so real and depressing that there was not an appetite to show a silly sketch about feminism. So I started adapting it for the book and one thing that was fun about it was casting it. When you work in one of these late-night shows, it was a long shot anytime you pitched a sketch for a celebrity that they would agree to do it. So being a writer on The Late Show, getting to cast a fancy sketch with the most important women in the world — not all of whom are even living — that was so fun! There was some catharsis in the storytelling [because] people are punished in it. I think that was because I wrote these over four years and so that was probably during some of the real dark times for women.

Then in another one of your stories “Big Time,” while fun, you really tackle the ins and outs of Hollywood, whether it be from reality TV to being woke. Can you talk about writing that story and any challenges when creating it? 

One of the challenges of the story was to make sure that the emotional core felt real and that I was tracking a transformation with the main character Ruby. I ultimately wanted it to be a story about a ruthless, ambitious woman who’s an actress in the 1940s [and] who’s on the cusp of breaking out and being one of the biggest stars. Then she gets flung into the future magically and has to make it today. I knew that there would be funny comedy opportunities with her. She’s woke for 1941 [and] this is all new to her. What was very important was to make sure I put front and center that her heart is in the right place. She thinks it is important to say the right words. It’s really a story about the magic and power of female friendship. She thinks that being “big time” is being a big success but really it’s having friends or having one best friend.

In your writing career thus far from The Onion to The Late Show, you’ve been able to deliver satirical comedy. From your experience, what would you say is the formula to writing a perfect satire?

It’s important you’re clear on what you’re taking aim at, having clarity on what you’re passing judgment on [and] what you’re highlighting as problematic. You need to have a really strong point of view. [Also] making sure that the story is well-paced, and it has enough jokes and lightness to let the reader think. Striking a balance between lightness and silliness and hard satirical punches is important when you’re writing because you can’t be relentless and you can’t tire the reader or the viewer.

This marks your first book. Do you envision yourself writing more? 

I want to always be working on books. Even though I’m not abandoning TV writing, I know I’d like to do another collection. I have been sketching out a novel. There’s actually stories from this collection that I’m interested in adapting, and I think it has lives as features [or] maybe as shows. In terms of fiction, now that I tasted the freedom, it just totally scrambled my DNA. I love the freedom and I love the challenge and I really can’t see myself ever stopping.

Now having written your first book, was there anything that you learned about yourself as a writer through this experience? 

I already knew this about myself, but it became clearer that I have go-to areas, go-to impulses and I almost have a bag of tricks. The challenge for me was surprising myself and not repeating myself. The biggest thing I learned is that I can do it because when I started, I hadn’t done it before. Until you crack the thing, you’re like, “Whoa, did I make a mistake? Am I going to have to send a humiliating email saying, ‘Hi, I don’t have anything’?” I didn’t really think that was going to happen, but I didn’t know! So even just proving to myself that I could write a novella and that I could sustain a story comedically and emotionally for that many pages, I’m thrilled!

Big Time is available now.

Interview edited for length and clarity.

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