Get Naked in the Rideshare with Comedy Couple Rebecca Shaw and Ben Kronengold

Raw vulnerability meets visceral Gen Z reactions to the real world in Naked in the Rideshare: Stories of Gross Miscalculations from HarperCollins. It’s the first short story collection by Rebecca Shaw and Ben Kronengold, the pair who first went viral for their 2018 Yale graduation speech before becoming the youngest comedy writers ever on The Tonight Show Starring Jimmy Fallon. 

Now, recently engaged, they sat down with me via Zoom to talk about their process, inspiration, and teamwork at the core of their latest project, an exaggerated exploration of coming-of-age tales: ritual sacrifices at summer camp, hook ups with a fairy god MILF, and a conference held outside of space and time with various selves ages one to 81.

After only a few minutes with Rebecca and Ben, it’s clear that their characters are made from the weirdest bits of themselves, injected with the same amount of hilarity and sincerity that makes their relationship and stories extraordinarily human, and their collection exceptional.

Note: This interview has been edited for length and clarity.

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Paste Magazine: Take us back to the beginning. How did the two of you meet? 

Ben Kronengold: When we were 17, Rebecca and I met at an accepted students meet-up for prefrosh in Washington Square Park. Everyone showed up tense, in their best Urban Outfitters flannels (it was 2014) and proceeded to do that anxious thing where they act like little adults. Then someone pointed out a woman in the park with about 30 pigeons on her arms, and I deadpanned, “Huh. Do you think she knows?” Everyone burst out laughing, we all became fast friends, and in that moment, Rebecca knew I was the one.

Rebecca Shaw: I was the only one who laughed. No one else made a sound. I’m pretty sure they all formed a friend group without us after that. But we stuck together and have been making each other laugh ever since. Now sometimes other people laugh, too.

Paste: What are your most cherished stories in the collection?

Shaw: We have a chapter called “Sky Not Found” about a small town that looks up into the sky one night and sees a giant error message. The town, accordingly, freaks the fuck out and questions everything, but it becomes this really human story about how communities deal with crisis. It captures what I love about the book which is: big premises, small stories. Also Ben wrote a story called “Fairy God MILF” about a 20-something guy who ends up sleeping with his childhood fairy godmother, which always makes me laugh. And then finally, “Yikies!” which is so gross you have to read it for yourself.  

Kronengold: I love this chapter called “Clarity.” It took us forever to crack a love story that felt fresh and weird and like we hadn’t read it before. Then Rebecca came up with this piece from the perspective of an engagement ring that made me laugh and cry at the same time. I also love “My College Friend, The Pope” about two post-grad friends who are on similar life paths, until one of them shoots ahead when the College of Cardinals elects her the new Pope. And I love “The Collected Works of Angsty Suburban White Kids Named Corey.”

Paste: What is the perfect writing scenario? Set the scene: where are you, what are you eating/drinking/smoking/listening to? 

Shaw: We have these two yellow couches in our apartment that are facing each other. We’ll start the day by sitting down on them and pitching each other—story ideas, characters, whatever we’ve got. We know we’re onto something when we make the other person laugh, and genuinely surprise them. We know we’re not onto something if we both came in with the same idea. 

Paste: This is hot. Speaking of, who in addition to Ryan Reynolds have you dreamt about having a sex contract with?

Kronengold: Ha, right! We have this piece in the book about the hypothetical sex contract we drew up in case Ryan Reynolds wanted to have a threesome with us. It was originally about Paul Rudd, but then we ended up working with Paul Rudd so we changed it….short answer: Paul Rudd.

Paste: What is the dumbest thing you ever fought about—at work or at home? But most importantly, WHO WON?

Shaw: We haven’t had a fight yet, but we’re sure we’ll resolve it with grace and diggity.

Kronengold: Dignity.

Shaw: What?

Kronengold: Nothing, you just said “diggity” instead of “dignity.”

Shaw: No I didn’t.

Kronengold: You did. Megan?

Paste (Megan): Oh I’m not…

Kronengold: “Diggity.”

Shaw: Fuck you.

Paste: Who would say they are the funnier one and who is actually the funnier one? 

Kronengold: The truth is that Rebecca’s a funnier joke writer, I’m a funnier structure guy.

Shaw: You know, how you meet a “structure guy” at the bar and he makes you laugh so hard, you want to go home with him.

Kronengold: That’s true. You don’t fuck the structure guy.

Shaw: No. But you marry the structure guy.

Kronengold: Aw.

Shaw: It’s true.

Kronengold: Thanks, Paste. I think we just got re-engaged.

Paste: Y’all are so cute. Give us dirt. What are some of your comedy-writing pet peeves?

Shaw: We don’t have many comedy-writing pet peeves, but we do tend to like comedy that tries. We love watching improv, and also stand-up, but when you go to a show where someone gets on stage, whips their phone out, and scrolls through their Notes app like, “Let’s see here…” It always just feels like, “C’mon, Brian. We put on jeans for this.”

Paste: How would Ben’s mom, one of the book’s breakout stars, describe the book to her friends?

Kronengold: Funny you should say that. I’ve been begging my mom to read “Actual Things Ben’s Mother Has Told Her Friends He Does For A Living” at our book launch. But my guess on how she’d describe the book to her friends? “Ben’s killing time before med school.”

Paste: The essay “Eustace, 1 Through 84” was both hysterical and heartwarming. I don’t know if I’m just going through something but damn I kind of got emotional? Sorry, that’s not a question for you. My question is: what inspired this piece? 

Shaw: That’s so kind of you! “Eustace” was really Ben’s brainchild. It was his love letter to boyhood through this kid who finds himself at a conference outside of space and time, where he’s brought together with every version of himself throughout the years. (So Eustace age four meets Eustace age 54, and so on.) It’s actually filled with a lot of details and nods to Ben’s own teenage years. Eustaces 22 and 23 chalking Eustace 14’s badge came from Ben’s sister chalking his ID, right?

Kronengold: Right. The part about the feeling of wanting to “get out of your own head, or your own way, or something” came from a conversation I had with my cousin Shaun before I tried my first beer. (Flex.) A lot of the piece was hard-fought, but the one part that wrote itself was the opening: 

Throughout his entire life, Eustace McDuff’s hair was invariably pubey. Somewhere between Art Garfunkel at Central Park and Justin Timberlake circa 2002. Some things are important to know because they come back later in the story. This, in the spirit of honesty, is not one of those things.

You take the layups you can get in a piece like that.

Paste: What are some of your favorite shows to watch together right now?

Shaw and Kronengold: Big Mouth.

Shaw: And FX’s Dave. And any competition shows like Ink Master.

Paste: Nice range. For everyone who will be immediately Googling you after reading, what’s next?

Kronengold: Since leaving The Tonight Show we’ve been writing TV and films, so we’ll probably do that for as long as they’ll let us.

Shaw: Then after that we’ll go to med school.

Naked in the Rideshare: Stories of Gross Miscalculations is on sale now.

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Megan Broussard is a writer and producer in New York City with work in The New Yorker, Marie Claire, New York Magazine’s The Cut, Slate, McSweeney’s, Reductress, and more. Follow her on Instagram and TikTok @megsbroussard.