Writer-comedian Josh Gondelman talks touring, the WGA strike, and the value of being a Pollyanna  

Josh Gondelman. // Photo by Mindy Tucker

It feels like Josh Gondelman is everywhere right now. Maybe you’ve heard him as a recurring panelist on NPR’s Wait, Wait…Don’t Tell Me!, or as a frequent guest on podcasts like Work Appropriate or You Are Good. Maybe you’re one of the many people who loved his “Modern Seinfeld” Twitter account. Are you a fan of The Marvelous Mrs. Maisel, Desus and Mero or Last Week Tonight? Gondelman worked on those, too.

In addition to all these accomplishments, Gondelman is also a frequently touring stand-up, who will bring his show to the Comedy Club of Kansas City June 4. Whether he’s up on stage, recording on mic or writing behind the scenes, Gondelman’s comedy is notable for its wit, warmth and unshowy kindness. Ahead of the comic’s visit next month, we discussed his touring schedule, the value of vulnerability in comedy and his work as a board member with the currently striking WGA East. 

The Pitch: It seems like you’re constantly on the road these days. Do you get energy from that? Is it exhausting?

Josh Gondelman: It’s really fun and exciting! For the last several years I’ve been in writers’ rooms for a lot of the time, even pre-pandemic, like January through November, working with scattered weeks off. I would do the bulk of my touring from November through early January. 

Since 2020 it’s been slower. I shot a special (People Pleaser, available on Amazon and Tubi) in 2021 right after I started doing stand-up again in person, a little run in Boston and Philly, a couple of scattered weeks in early 2022, and then really heavy through the following winter since Desus and Mero and Mrs Maisel wrapped up. 

Because I’m not doing theaters every night, or on a tour bus for two straight weeks, it’s a lot of going out and back. I’m not in a writer’s room, but it’s fairly balanced. I’ll be out for two-five days at a time, then back for up to a week and a half. While I’m home I’m not working full time. I’m pitching freelance, doing podcasts. 

It’s actually been the most balanced I’ve gotten to be since doing stand-up, which is nice. The schedule’s been heavy, but I joke that if I take a shower at a hotel, and then later I step in a puddle with a sock on, that’s the moment where it’s suddenly like Bob Seger, (singing) “Turn the Page.”

Do you think the pandemic, or the current state of the world that’s come after has evolved your comedy at all? 

I think it helped me. I used that time to really look inward and write about granular stuff that doesn’t feel like a story. While the world was so turbulent, so little was happening in my day-to-day life that I had to scrape the crevices of my brain for thoughts and insights, which were different from other people’s insights. There was such a monoculture of cabin fever, so to write for myself about anything other than that was a challenge. 

I have a bit on my special that was about a friend texting me about a sex dream where I showed up after the sex. It was such a brief interaction, but that was a wrinkle in my day outside the specific goofing around Maris and I were doing. So it was like, “Oh! Novelty!” Looking for the slightest novelties became an interesting takeaway from having to make comedy during that time.

Also, I got a lot out of doing Zoom shows. There are people who feed off audiences a little more, which I don’t always find rewarding. My friend Alice Fraser, a comic in Australia, says she considers herself a brain in a jar, and I feel very similarly. Being a square on a screen and getting literally any laughs was like “We’re making progress! Good enough.” I tried to take pleasure in figuring it out more than the roar of a crowd.

Your Substack newsletter, That’s Marvelous!, where you give pep talks to public figures and your readers, is consistently one of the highlights of my week. How did you decide you wanted the focus to be pep talks? What do you enjoy about giving them?

It feels like the kind of thing that people really take to that I’ve done in the past, like on Twitter I do that occasionally. That’s something people always liked and I felt like a newsletter was a good vehicle for that. It was easily replicable week to week. I wasn’t sure about the legs of it, since I don’t give advice, I’m just being reassuring and enthusiastic. I wasn’t sure how much I could do before recycling everything. 

But what people write in is so specific that my answers are specific. Newswise you can do a lot of mean jokes if you say it with a smile. I’ve always worked better in that mode. Bitterness doesn’t come out naturally for me. It meshes more naturally when I talk about things I’m enthusiastic about. 

So, speaking of bitterness not coming easy to you, that speaks to a trend I’m curious about. When I think of popular comedians right now, or at least the people whose work I’m enjoying—like you, but also Joe Pera, Atsuko Okatsuka or Taylor Tomlinson, it feels like there’s a growing appreciation for empathy and sincerity. Do you think there’s a bigger audience for that right now? 

It feels like there’s a big audience for comedy and for one thing, there are so many outlets to create comedy of any specific vibe. If you want to make a podcast where you give yourself diarrhea and talk about that to no one, you can. If you want to do something like (Chris Gethard’s podcast) Beautiful Anonymous, you can, and hope it catches on. Because of the breadth of what’s out there, people can find what they like instead of the same things they’d see on TV, or whoever’s coming through their city. Distribution has allowed for that for sure.

I think it’s beautiful how many other voices there are and points of view coming to comedy that were marginalized by the industry for so long. Someone like Atsuko had this great HBO special that was a single narrative. I recently worked with River Butcher on the JoCo Cruise, and he has a special coming out. I think it’s cool you can find the comedy you’re looking for, and as a comedian you can reach out and find the people who like what you do. I don’t have to cram everything into 5 minutes that I hope Letterman takes and that makes me famous. 

How have you seen that in the audiences you’ve encountered?

I feel like any heckling I’ve gotten throughout my career has been so much less demoralizing than audience members who fall asleep during my sets. That’s worse. Like, “Your words make me feel nothing, because I’m opting out of consciousness.” 

I think this tour I’m on, more people than ever are coming to see me. I think I’m better than I’ve ever been, which is just based on practice. If there are 200 people in a room to see a show I’m doing at club, and 100 people are there because they’re psyched to see me for things I’ve been on and worked on, they’re like the seed for the audience, and the other half is there because they got like free tickets or they’re big comedy fans. The enthusiastic half is good to win over the other half. It’s great on both sides. Having big laughs in the room is persuasive. 

I’ve had such a nice time being able to go to places and seeing people who are there to see me. I’ve had audiences of 300 to 400 in some cities, 50-seaters in other places. Instead of being jealous of my friends, I get to be like, “It’s so cool people are coming to see me intentionally.” Five years ago, I was not at that level. I’m psyched, and I want to do a good show for the people who show up. 

Do you like to spend extra time in the places you go?

I want to use my time mindfully, but also not tourist myself into oblivion. Sometimes it’s just about finding a friend in town, grabbing a good cocktail and hanging out for an hour after the show. I’m gonna eat indulgent food too, but you can’t make every place like a state fair. I’ll try chowder or ribs, but I also have to eat things that keep me alive, like with actual nutrients. Like, for every hot dog cake I eat, I have to go “Do you have a kale stuffed kale salad?” 

I’m so psyched to do that kind of thing, and get a literal local flavor of places I get to go. 

I do really appreciate getting to travel for work outside the US. Doing those little things like finding the best local coffee shop that’s good to sit in and write. Finding cozy-feeling nooks and crannies and occasional tourist stuff. You can tell I write the pep talk newsletter because I’m such a pollyanna!

On a more serious note, you’re on the board for the WGA East, and in the middle of this hugely important strike. How is morale right now on the picket lines?

There is a huge sense of solidarity on the picket lines I’ve been out on! None of us WANT to be on strike, but the WGA authorized the action with a 97.85% vote because of how important these negotiations are. 

It’s extremely heartening to see members of other unions (even ones from outside our industry) show up to offer support too! The WGA West has so many more members, and they’ve been turning out in huge numbers, but I think the relatively small and scrappy East pickets have been really wonderful and effective at creating awareness and in some cases slowing down productions!

How are you balancing the strike and negotiations with your touring schedule now that you’re back on the road?

So far I’ve been able to do both things full-throttle, and my secret is that I am constantly sleepy! It’s really been cutting into my staying out late and drinking with other comedians, which ultimately is probably necessary anyway as I get older!

Apart from coming to see you, how can those of us who aren’t located in NY and LA support the strike?

The Entertainment Community Fund has a donation option to support film and tv workers if people have a few bucks to spare! I’m donating all the profits from my tour posters as well, in an effort to be helpful even when I’m not marching. Vocal support of the WGA on social media is also super helpful and appreciated! And, if you end up in any cities with production going on, we’re trying to organize picket lines outside of NYC and LA. In-person support is always great too!