Josh Gondelman Is a Cozy Cardigan

The writer/comedian is really nice. Like, suspiciously nice.

“I’m like if a cardigan were a person,” Josh Gondelman announces in the opening minutes of his new comedy album Dancing on a Weeknight. I’ve heard him say this before—for example, on Late Night with Seth Meyers—but meeting him in person really hammers the point home. He used to be a preschool teacher (“We’re gentle and cowardly people,” he’s explained in reference to the right-wing pivot to arming school teachers) and he is that rare breed of white male who seems neither threatening, nor problematic, nor cocky. His comedy is compassionate and benign.

Both a stand-up comedian and a late-night staffer, Gondelman wrote for HBO’s Last Week Tonight with John Oliver for years (winning two Peabodys and three Emmys) but recently moved on to writing for Desus & Mero, which debuted on Showtime in February. Clearly he’s made a good impression on the showrunners: Desus recently tweeted, “Josh just be in the office happy as hell. It’s infectious. Makes me sick.”

Dancing on a Weeknight focuses on Gondelman’s happy marriage to writer Maris Kreizman and their beloved dog Bizzy, who Josh’s neighbor has casually greeted by name, causing him to suspect that man heard his Ja Rule and Notorious B.I.G. Bizzy-serenades through the walls (“You can find me in the club, snuggling a pug”). Even his political jokes are generous of spirit: he admires the cold poise of Hillary Clinton (“When she smiles, she looks like she knows how you’re gonna die”) and the gruff chutzpah of Bernie Sanders, whose policies he compares to an old dude ordering off-menu at a Dunkin’ Donuts (“They don’t want ya to have it, but they’ll give it to ya if ya ask!”).

In addition to Gondelman’s third album, his second book Nice Try (a collection of personal essays) is slated for release in September. We met up before his impromptu appearance at UCB Franklin in LA to discuss how deeply his wife’s opinions factor into his comedy routine, the benefits of not reading your own reviews, and the difference between being nice and being good.

A lot of people seem to like you. Everyone I follow on Twitter always seems to be promoting you very genuinely. How do you think that platform has helped or hurt your career?

The first big thing I did was the Modern Seinfeld Twitter account that I co-wrote with my friend Jack Moore. I had already been doing stand-up for a while, but that got me in the mix for things at a higher level. I also sort of met my wife through Twitter—we met in real life, but we knew of each other through Twitter. There are ways it can be a hindrance: it’s a time suck, you end up arguing with people, and it’s not a substitute for doing other kinds of work, though sometimes you feel like it is. Just the community of comics…there’s people I talk to on there frequently, but I’m not on good enough terms to call them or text. A lovely thing to be able to do is tell people you enjoy their work. I try to do that with people I’m a fan of. There’s a lot of ways to use it for good.

You don’t argue with people on Twitter, do you?

I do occasionally. I don’t like when people are mean and petty and shitty online. I’m of two minds: I hate the feeling of arguing with somebody over basically nothing, but also when people are like this, they should be told that it’s the wrong way to behave. There should be some negative feedback—not abusive or grotesque, but just, “Hey, I think you’re out of line.”

Do you think that gets through to them?

Sometimes. I’ve had long back-and-forths with people. They come in hot, and you go, “Hey man, I don’t know what you mean by that, but I think it’s a pretty hurtful thing you’re trying to do there.”

I’ve noticed people appreciate how you speak about your wife lovingly instead of critically. You don’t make snide jokes about how shitty the relationship is, the way someone like Louis C.K. used to do. Is that a conscious decision on your part? Would you ever describe the hard times, if things were going badly?

“I try not to use the stage as a venue for airing my own personal grievances with people that I love. I try to present [my wife] in a light she doesn’t mind strangers hearing every night.”

That’s very nice, that people say that. I try not to read comments… I mean, I’m not like, “Don’t tell me!” But I think my relationship with Maris is paramount in my life, and there are things about it that are funny and I like to relay, but I always want to put her in the light that I see her in big-picture. I don’t make a lot of comedy and art from places of anger, so if there was something I was frustrated about in my relationship, it wouldn’t be the kind of stuff that makes it to stage anyway. It’s off-tone for my act. Also, I try not to use the stage as a venue for airing my own personal grievances with people that I love. I try to present her in a light she doesn’t mind strangers hearing every night.

Your wife is a big part of the new album. Does she enjoy being fodder for your act?

There are things I’ve said that she wanted to set the record straight on, so I’ve modified it. I don’t want to misrepresent her. I don’t want the jokes to be at her expense.

You’ll actually modify jokes at her suggestion?

Yeah. Like on the new album, there’s a joke about her reading books before bed, and she feels like I’m giving her too much credit for being a mentally at-ease person who’s a sound sleeper. But she’s okay with that embellishment, because I’m embellishing from a true place and I’m not making her look worse.

I have a new joke we were just talking about in the car from the airport—I talk about how there are opinions that I have, that I don’t have any backup for, but they’re her opinions and now they’re mine. I just picked them up. These are things she believes, and I trust her. How great is it to think something without having to learn anything?

But I say she gets some of that from me too—it’s not a one-way, it’s not her hectoring me. She has very firm opinions now about Dunkin’ Donuts and LeBron James, but if I died she’d forget which one was the basketball. I think she’s okay with that joke, but she brought it up as something like, “I know what a basketball is.” Which is true. But she doesn’t care. I want to represent her not just fairly, but in a way she feels pleased that I’m telling people.

A lot of humor is mean-spirited or mocking. It’s hard to be funny and not at all mean. Like John Mulaney isn’t mean, though he’s definitely dark at times.

And he has that line in his new special, “My wife is a bitch and I like her so much.” I was so impressed and delighted with that. As long as you never say “she’s a bitch and I don’t like her.” For that to be in-bounds in their relationship, I think is really beautiful. Especially in the John Mulaney canon, there are so many jokes about her being an assertive, capable person. I think he’s very admiring of it.

Do you think people crave nasty humor and your niceness somewhat holds you back, or are you comfortable with that being your niche?

Both things can be true. I think there’s lots of good mean comedy. Not every mean joke is funny, but it’s so funny to be mean to someone who stinks. I laugh out loud at Desus and Mero…they do a very funny job of being mean to people who are just the worst, and knowing who to lift up and appreciate. I don’t think it holds me back—I feel like I express a pretty varied emotional palette, comedically—it just comes out very friendly. It’s a style choice more than a content choice. It’s something I do differently than a lot of people, so it’s fun to lean into.

What is your next book Nice Try about?

The premise behind it is, I was a very sweet, nice kid, which is something people say about me a lot. It’s flattering, but it’s not the same as being a good person. It’s about the tension between being nice and being good, and how to be a well-rounded adult who contributes to the world, instead of just being a pleasant person. With good, there’s more of a moral judgement. That’s what I’m trying to strive for, in addition to politeness.

“Nice comes easy to me, and sometimes it’s easy to get a lot of credit for being nice, and pat yourself on the back instead of taking the next step toward doing more good.”

Some people are kind and good, but it’s hard for them to be nice—they don’t have the social awareness or know how to come across as warm and friendly.

That’s true. Good is paramount. Nice comes easy to me, and sometimes it’s easy to get a lot of credit for being nice, and pat yourself on the back instead of taking the next step toward doing more good.

Is it a lot of pressure, having everyone think you’re so nice? Do you ever second-guess yourself like, “Wait, am I really this nice?”

I think I worry about keeping up with people’s positive impression of me. And that’s an okay pressure to have. I don’t feel pigeonholed, but people say such kind things about me, and I’m appreciative that that’s my reputation, so I try to act in a way befitting of that. But again, it’s not nice to be like, ‘Hey man you’re being a dickhead’ online, but getting out of that nice pocket and doing something that’s uncomfortable—that’s maybe a good thing to do.

You said on Twitter recently that you’re not reading any press about your album. Is that a new policy, or something you’ve always abided by?

I’m trying to read it less. I’m trying not to be thirsty for approval and validation. I’ve retweeted nice things people said about the album, and I take it to heart. This is so fucking pretentious, but…a David Foster Wallace thing I read in an interview was, “Critics write and it’s not for you.” A review of my album is not written with me as the audience. There was that thing with Lizzo, who is deservedly beloved with so much positive press, tweeting about how critics should be unemployed. I don’t think that, but also I can see getting mad at reading criticism you don’t agree with. I’m trying to take that out of the equation. Why would I absorb it for the potential dopamine rush of someone saying I did a good job? It’s not worth the risk.

I’d like to have an open and candid relationship. I’m so happy to be talking to you about this and I hope you enjoyed the album and this conversation, but at the same time, if you didn’t, that’s totally your prerogative. For me to open myself up to being hurt by that differing perspective…I don’t need to set the record straight. I’m not dismissive of their [critics’] hard work and investment in the work I did, so I want to share it. But it’s a tough tightrope.

I’m sure if I read things people wrote about me, I would learn about myself—but I’m trying not to use that as the metric of, “I’m good or bad.” FL

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