How Josh Gondelman Became Twitter’s Pep-Talk Master

Josh Gondelman. Photo: Mindy Tucker

In describing his decidedly unhip but sweetly calm essence on the opening track of his new album, Dancing on a Weeknight, Josh Gondelman says, “I’m like if a cardigan were a person.” But clearly there’s a place in comedy for someone so buttoned-up.

He first garnered attention for co-creating the Modern Seinfeld Twitter account in 2012. That nabbed Gondelman a Shorty Award for social media excellence in the Best Fake Account category. As his reputation for being one of stand-up comedy’s nicest people grew, he won two Peabodys and three Emmys for his writing work on Last Week Tonight. Showtime recently plucked him away from HBO to write and produce for Desus & Mero, which debuted in February. In addition to Gondelman’s third album, set to be released on vinyl and streaming April 19, his second book, Nice Try, is also slated to hit stores in September. He’s also married, has a pug, and often offers pep talks to struggling Twitter followers in need of a pick-me-up.

Vulture lured Gondelman away from his busy schedule to talk about how he manages both his work and private life, the origins of his Twitter pep talks, what it’s like as a nice guy to write for roast-ready Desus and Mero, and if he ever gets angry.

Congrats on the new album! It’s very funny, and you do nothing to dispel the rumor that you’re the “nicest guy in comedy.” Is that something you embrace or are you over it already?
If there’s any reason that I would want to dispel that I’m “the nice one,” it’s not because I think I’m not nice or I think that’s an unflattering tag to have affixed to me, it’s just that I think there are so many people in comedy that are very kind and wonderful that get less recognition for it.

I think it’s very exciting to have earned any kind of reputation in comedy. [Laughs.] Obviously there are some comedians that are “bad,” but for so many years you’re just kind of a person who shows up. To be known for anything, especially something that’s positive, is just warming.

Is there anything that gets you down, angry, or frustrated?
I’ll get grumpy about if I miss out on a career opportunity that I’m looking for or have a weird interaction with a friend or an acquaintance. I’ll stomp around for a day. It’s not that that never happens. The relentless horror of bad news in the world is something that is a personal drain — although not as much as it is for people, I think, who are more directly impacted by the actualities of the happenings, rather than just how depressing and demoralizing it is. Living in the world, and being attuned to what’s happening in it, is discouraging.

But I think I just have a very fortunate brain, where I’m largely upbeat and bounce back from personal hardships pretty well. And I’m a person who, recently at least, hasn’t dealt with a lot of big-picture personal tragedy. I don’t want to say, “Oh, yeah, I can get through anything.” It’s easy to say that when not that much bad is happening directly to me.

Tell me about your transition from Last Week Tonight to Desus & Mero and the challenges of working on such a different show that doesn’t seem to match your profile. At the beginning of the first episode they roast Barack Obama of all people. So are you trying to shake things up for yourself, career-wise, here?
There’s more similarity between Desus & Mero and Last Week Tonight than I think is surface-apparent. The big one is that I think the hosts of the show want to go on television and say funny things, make funny commentary on the world that is sincere and thoughtful. And I think sometimes the stories that they comment on are different, but [there’s also this common] idea of having a really strong point of view and wanting to represent themselves sincerely while joking.

I’m thrilled to be on a show that is being built from the ground up, in one respect, but in another respect the hosts have hosted hundreds of shows together. So there’s a real joy working on a new project with people who have a honed, refined voice and skill set. [In my job] it’s a mix of sketches, interview prep, pitching guests or things to do with guests. I get to work on the edit of the show, which is really exciting — to help shape what happens in the studio into what goes on TV. Mostly I’m just trying to stay out of the way and let the hosts be funny and good at what they do, and just help smoosh that into the shape of 30 minutes of television.

So you’re doing that full-time, you’re working on your stand-up to the point where you have a new album out, your writing has shown up in The New Yorker, McSweeney’s, and New York Magazine, and you have a book on the way. How are you able to find time for all this productivity?
I do a lot of stand-up at night, which is not a conflict of interest with my day job — or at least not a time conflict with my day job. Last year, I was working in the office of Last Week Tonight Wednesday through Sunday, and then basically hanging out at home and working on my book Mondays and Tuesdays. So that was roughly a year, maybe a little less, that I was doing that.

Fortunately, with the show, we had about eight weeks between seasons, and I would go on the road and take the stand-up material that I’d been working on and shape it into an hour, which is how I got the album. But also, this is four years between when the book I wrote with Joe Berkowitz came out and when my solo book is coming out. With the stand-up album, it’s about three years between my last album and this one.

So I think I move slower. Some people do a new hour of stand-up every 12 to 18 months, and some people do a new book every 24 months or whatever. I just have to be more forgiving with myself, like, Okay, I can’t keep that pace with my friends who are full-time stand-ups. And I wasn’t ready to just write a book right after my last book because I had all these other professional obligations. I think a lot of it is using my time wisely, and an even bigger part of it is being okay with not using 100 percent of my time to work, and not producing work at the same level as friends and peers — the people who are better than me, and substantially more accomplished and talented. [Laughs.]

I’ll be out at clubs in New York and see friends with, like, ten minutes of new stuff since the last time I’d seen them, and I’m so impressed and so jealous. I just have to be, like, “That’s great,” and I can love that and be motivated by that. But I can’t let myself get down about it because it’s just not possible for me to do that.

Headline: “Josh Gondelman Is Stomping Around Today Because Colin Quinn Got a New One-man Show Up.”
Right!? [Laughs.] I can’t get mad at that, and I don’t get mad. I’d never be mad at Colin Quinn, but it has been a process to learn that I have this lane that I’m developing and carving out that’s a little bit different.

[That line of thinking] also makes it easier to flatter myself, and be like, “Well, if I had every day, I could write a new hour this year.” That’s very thrilling. I’d probably be a lot better if I wasn’t so busy; that’s what the problem is.

On top of all of this, you’ve also been married for close to two years now. How do you pull off the whole work-life balancing act?
I think the work-life balance is about being a good partner. Again, this is something that took years, and I was very bad at it when I was younger. I’m trying to be an increasingly available, attentive, collaborative partner. I try to support my wife; I’m very enthusiastic about her career, and she’s, fortunately, very supportive of mine. I just feel stable enough in my professional life that I am happy to take nights off and just do fun things or hang out at home. And I have this person in my life that I’m a giant fan of and I want to spend time with her a lot. Since I’ve been doing comedy, I don’t think I’ve had the first part in line quite so much, of just willing to be a good partner — and, obviously, I just love my wife so much.

And you also find time to launch football-game-prompted charities. Tell me about that.
I’d kind of given up on football, but my grandmother, as she was dying in 2014, she got really into the Patriots that season. It kind of dragged me back in. I got out of the NFL for CTE reasons and political reasons. It didn’t feel like fun escapism; it felt like a keen awareness of big, global problems. But my grandma got back in, which got me back in. It was a thing I could talk to her about, so I stayed current with the Patriots. My grandmother was cremated in a Tom Brady jersey, which I have a joke about on my last album, so that’s how deep it goes.

So when the Patriots were in the Super Bowl in 2017, it was right after Trump’s inauguration. [Owner] Bob Kraft, [head coach] Bill Belichick, and Tom Brady were all at some level Trump people. It felt a little grimy for me to be, like, cheering wholeheartedly for this team linked to this gross political figure. My friend and I came up with this idea to do a fundraising drive for people who watch the Super Bowl. It felt more feasible to harness the consciences of people who watched the game and felt conflicted, rather than ask people to take the step to not watch the biggest television event of the year.

The way it works is, you find a generally progressive charity that you like — this year I did the Loyola Immigrant Justice Clinic and the NAACP Legal Defense Fund. And then you donate for any reason you like: a Patriots touchdown, a Patriots field goal. I donated for a Tom Brady pick-six, which is technically a touchdown, so I donated for that, furiously. We use the hashtag #AGoodGame just to track it.

The Patriots have been in three straight Super Bowls and we’ve done it three years in a row.

Do you know how much money you’ve helped raise?
I don’t, but the first year, which was the biggest, I think we raised over $100,000.

And you’ll hop on Twitter and do these pep talks for followers that might be struggling, emotionally or otherwise. You’ll send out a tweet and ask if anyone needs a pep talk, and then respond to those who say they do in the thread. How did that get started?
I was in a weird, bad place with my own career. This was late 2013, maybe. I had a gig cancel on me as I was getting ready to leave for it, out of state. I was pretty bummed out. I thought, I would like to feel better. I felt very needy, sincerely. That feels gross, but I was in a needy place, and I thought instead of asking people to do a nice thing for me, maybe there’s a way I can offer to do a small, nice thing for someone else, and that will scratch the same itch. All I needed was a kind word, and being able to see that other people were feeling bad, too, it helps to hear someone say, “It’s not always gonna feel like this.”

Looking at a couple of them, you really more often type out a quick “attaboy” kind of thing, but I am curious to know if you’ve ever had a more drawn-out discourse where you guided someone through a crisis of some sort.
I don’t think, necessarily, I’m qualified for that specifically, but I’ve had people write back a couple weeks later who’ve said, “Hey, thanks. I had this job interview that I was nervous about,” or, “I had a family member that was in a bad place, and getting a little support was meaningful.” That’s very heartening and gratifying. It helps me feel connected to people, which, really, that’s what I wanted. I do it a lot when I’m on the road or I do it when I come home late at night from a show and my wife’s asleep, and I feel a little bit removed from people. It’s a nice little connection and a very warming feeling.

From afar it seems as though life for you is really clicking into place — creatively, professionally, personally. I mean, you’ve even got the dog. Do you take the time to feel grateful, and what advice do you give to people generally seeking that kind of contentment?
I feel really good. I’m very grateful for the wonderful, exciting opportunities I’ve had the last several years, and I’m really fortunate in that way. I think about that a lot. I feel like I work hard, but it’s also a lot of what kind of advantages did you start with and where you fall in. A lot of it is very circumstantial.

Once you have the ability to meet your basic needs, which obviously is the first thing — I can’t be like, “Follow your dreams, and get evicted!” — but having things that you do just for you, creatively or hobby-wise, something that you enjoy and feel expert over, and there’s no outside reward, is really helpful. You feel like you’re working for your own purposes rather than part of a cog in show business or the medical industry, whatever you’re doing. Having something that is just yours that you cultivate is really helpful and stabilizing.

This interview has been edited and condensed.

How Josh Gondelman Became Twitter’s Pep-Talk Master