Hey y’all, before the launch of season 2 of Who the Folk Cincinnati, we’ve got a special episode with Josh Gondelman.
Josh is an Emmy Award-winning comedian, author, and writer. He has worked on shows such as Last Week Tonight with John Oliver and Desus & Mero. Josh has written for Esquire magazine, The New Yorker, and The New York Times.
His last two stand-up specials, “People Pleaser” and “Positive Reinforcement,” are available online and on YouTube. Josh is bringing his new hour to the Commonwealth Comedy Club in Northern Kentucky this weekend, April 10-11th.
If you have suggestions for future Who the Folk?! Cincinnati podcast guests, please fill out this form.
Below is an edited transcript of our conversation. It has been edited for length and clarity. We do our best to make sure everything’s accurate, but if you spot a typo or mistake, that’s on us. We hope you’ll enjoy listening — and reading — along!
Sam Fisher:
Josh Gondelman, thank you so much for joining us. I’m sure some of our listeners know your voice after hearing it on Wait Wait… Don’t Tell Me! or watching your stand-up specials, or maybe even in the background if they were fans of Desus and Mero.
Is this your first time in the Cincinnati–Northern Kentucky tri-state area?
Josh Gondelman:
Well, thank you for having me. I’ve been through a couple of times. I’ve performed at Commonwealth before, and I love it. I really like a funky, unique space that’s been reclaimed and repurposed for comedy.
I’ve also performed at the Comet in Cincinnati proper, which was a blast. And then with the Wait Wait stand-up tour, I performed—I think it was at the Taft Theatre? Yeah, that was great. I love the audiences here. I love the town.
Sam Fisher:
The Taft is a big theater. How did you start to get into comedy? When did you really start?
Josh Gondelman:
When I went to Brandeis, I started doing improv and a little stand-up on campus, but college kind of counts and kind of doesn’t. It’s like lifting weights underwater—you’re like, “Oh, this is easier than I thought.”
The summer after my freshman year, a friend of mine, Joe Smith—not a fake name—started doing open mics in Boston at Dick Doherty’s Comedy Vault. A childhood friend of mine was like, “Joe’s doing it—why aren’t you?” So I kind of got bullied into starting stand-up.
Sam Fisher:
Peer pressure can be good sometimes.
Josh Gondelman:
I grew up just outside Boston, so that tone—“What’s your problem, kid? Do it”—that’s very familiar.
Sam Fisher:
Brookline-ish area?
Josh Gondelman:
I grew up in Stoneham. My buddies are from Peabody—North Shore. I knew them through a Jewish day camp, Camp Menorah up in Essex. So very North Shore.
Sam Fisher:
I’m a little surprised—maybe this is my own internalized antisemitism—but I feel like Brandeis audiences might be tough. Very intellectually challenging.
Josh Gondelman:
That’s a very funny way to put it. I found them pretty warm and friendly. I think being part of that community helped—there’s a sense of, “That’s one of our guys.”
But I do think it’s interesting: I’ve often done better with more discerning crowds than with “party atmosphere” crowds. If the expectation is, “We’re here to have a wild time,” that can be tough if you’re not bringing that energy. And I don’t have a ton of party in me.
Sam Fisher:
So you start in college, then Boston, which is where a lot of big stand-ups come up. That had to be a big shift in audiences.
Josh Gondelman:
Yeah, totally. I’ve always thought of a Boston crowd as like a pirate ship—they want you to prove you’re the captain. It’s rowdier, but not hostile. It’s more like, “You think you’re better than me? Prove it.”
And one thing I loved about Boston is you’d do all kinds of rooms. A traditional club, an artsy room in Cambridge, a fundraiser at an Elks Lodge, a college showcase. It was great cross-training—you figure out where you fit and how to play different spaces.
Sam Fisher:
That’s almost a perfect training ground.
Josh Gondelman:
It really is. If you only perform in one kind of room, it can be a splash of cold water when you step outside that.
If you’re used to artsy rooms, you might struggle in the back of a restaurant where people are eating dinner. And if you’re used to rowdy bar shows, you might not know what to do when people are actually listening.
Sam Fisher:
So you’re doing your comedy cross-training in Boston. What takes you to the next step—moving to New York?
Josh Gondelman:
The bus—Megabus days.
I was teaching preschool in Boston and doing stand-up around New England. I won a competition in Atlanta, which got me on the road a bit. That made me realize I’d kind of hit the ceiling of what I could do from Boston, especially because I wanted to write more.
Around the same time, I had a breakup, then started dating someone in New York. Everything lined up. I gave myself one more year to save money and work on my act, then moved in summer 2011.
Sam Fisher:
When did writing start becoming a bigger part of what you were doing?
Josh Gondelman:
In the lead-up. I figured, if I want to write more, I should start writing more. So I started pitching to places like McSweeney’s while I was still in Boston.
Then in New York, I ramped it up. I was meeting more people in media, doing freelance work, and I had some traction on Twitter. My friend Jacqueline and I had an account called “Modern Seinfeld,” and that got some attention.
That led to submitting for TV writing—Billy on the Street, then Last Week Tonight with John Oliver, where I did social media and digital writing for a year and then was a staff writer for four years.
Sam Fisher:
What were your Jewish parents saying when you decided to leave a stable teaching job with health insurance?
Josh Gondelman:
My mom literally said, “Just make sure you have health insurance.”
They were really supportive. And honestly, they were right. Health insurance is huge. My wife has type 1 diabetes, and being in the Writers Guild has meant stable coverage for years. That’s been life-changing.
Sam Fisher:
You mentioned union work—does that connect to your Jewish identity?
Josh Gondelman:
Yeah. During the 2023 strikes, my dad sent me a pamphlet my great-grandfather wrote about unionism from a Jewish spiritual perspective.
So I think I’ve got some “mouthy union shit-starter Jew” in my blood. It means a lot to me—I was just in L.A. working on contract negotiations.
Sam Fisher:
You were at Last Week Tonight for five years. I’ve always wondered—when you win an Emmy, does everyone get one?
Josh Gondelman:
For late-night, yes—everyone wins. I think technically you have to pay for the statue, but the show covered ours.
I brought mine to my parents’ house, and my dad put it on a high shelf behind a childhood photo and said, “We didn’t win it.” And I was like, yeah, that tracks.
Sam Fisher:
How did you end up working with Desus and Mero?
Josh Gondelman:
They were moving from Viceland to Showtime and scaling up. I got brought in to interview and ended up as a writer-producer, then head writer in the final season.
It was a really wonderful, diverse staff. A lot of people I still love and stay in touch with.
Sam Fisher:
Were you still doing stand-up during that time?
Josh Gondelman:
Yeah, the whole time. Probably more than I am now, but I wasn’t touring as much because of the schedule.
After the show ended, I went on the road pretty hard. During the 2023 strikes, stand-up became my main creative outlet. That’s when I realized I was ready to record a new special.
Sam Fisher:
Does your Jewishness inform your comedy?
Josh Gondelman:
Yeah. I feel comedically Jewish in the sense that I grew up on Mel Brooks, Seinfeld, that whole sensibility of questioning things.
There’s also a spiritual side—tikkun olam. I want to make comedy that feels warm and inviting, especially for people who might not always feel welcome in comedy spaces.
Sam Fisher:
What themes are you working through in your new hour?
Josh Gondelman:
It’s less explicitly Jewish, but still tonally Jewish. I’m in my early 40s, married, thinking about family differently.
And as the world has gotten more turbulent, I’ve leaned toward making comedy a more cozy space. Not ignoring serious issues, but not making the show a place where people feel worse.
Sam Fisher:
Is there a Jewish teaching you come back to?
Josh Gondelman:
Yeah, I mean, something I come back to all the time—and this is very basic, like Judaism 201—but it really sticks with me. It’s the kind of triplicate: If I am not for myself, who will be? If I am only for myself, what am I? If not now, when?
I think that’s such a powerful guiding philosophy. It’s like, OK, I’ve got to be who I am, because no one else is going to do that for me. But I also can’t just be for myself or only care about people who look like me or think like me or come from the same place I do. Because then what am I?
So it’s this balance of self-respect and responsibility to others. And then the “if not now, when” part adds this urgency—it’s not just theoretical. It’s like, you have to act on that balance. You have to show up for people, you have to do the work, you have to try to make things better in whatever way you can.
I find myself coming back to that a lot, because it’s simple, but it kind of contains everything.
Sam Fisher:
Did it take you a long time to find your voice?
Josh Gondelman:
Yeah. Early on, I tried being edgier, a little nastier, and it just didn’t stick.
Working at Last Week Tonight really reinforced that if you work hard enough, you can write the joke you actually want to write—you don’t have to fall back on “it’s just a joke.”
Sam Fisher:
How has your writing process evolved?
Josh Gondelman:
I try to write things down, I forget them. Some ideas come from conversations with friends, some from the stage.
Now I have more stage time, so I can riff a little more, but I still like to come in prepared. I’m not someone who can just improvise an hour from scratch.
Sam Fisher:
Let’s talk Wait Wait… Don’t Tell Me!. How did that come about?
Josh Gondelman:
In 2019, I got connected to a related podcast through a friend. That went well, and they invited me to audition—basically doing the show live in Chicago.
It clicked. The staff is wonderful, they prepare you really well, and it’s just a great experience.
Sam Fisher:
How much of the show is riffing that doesn’t make it to air?
Josh Gondelman:
A lot. The recordings are about 2 hours long for a show that’s about 50 minutes. They bank extra material for future episodes.
Sam Fisher:
What’s harder—writing a fake news story or the real one when you try to fool the listener?
Josh Gondelman:
Fake news. With real news, it’s fact-joke, fact-joke. With fake, you have to build the whole premise and sustain it for a full minute.
Sam Fisher:
You’ve hosted as well as been a panelist. Do you have a preference?
Josh Gondelman:
Being a panelist is easier—you just jump in when you have something funny. Hosting is more intricate.
I once almost let Malala hang up without playing the game segment. The producers were in my ear like, “Don’t let her go!”
Sam Fisher:
You’ll be in Cincinnati April 10 and 11 at Commonwealth Comedy Club—four shows.
Josh Gondelman:
Yes, Friday and Saturday, four shows. I love the room, I love the crowds. I’m really excited.
Sam Fisher:
Anything we didn’t cover?
Josh Gondelman:
I write a weekly newsletter called That’s Marvelous. It’s jokes, pep talks, and tour dates. You can subscribe for free or paid.
And I’m on Instagram, BlueSky, and TikTok at @joshgondelman.
Sam Fisher:
Josh, thank you so much. You’re a real mensch.
Josh Gondelman:
Thank you—this was a blast.