“It’s about creating a feeling of warmth along with humor”: Josh Gondelman on Comedy, Writing, and His New Album -The Toast

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Josh Gondelman is one of the most consistently kind and hilarious people I’ve met on Twitter, and I was thrilled but not remotely surprised when we met not long ago at a launch event for his book and I discovered that he is the same funny, thoughtful force for good in real life. A writer and comedian who has earned both a Peabody Award and an Emmy nomination for his work on Last Week Tonight with John Oliver, Josh’s writing has also appeared in New York Magazine, McSweeney’s, BuzzFeed, Esquire, The New Yorker, and on this very site. Hinew comedy album, “Physical Whisper,” came out last Friday, and tomorrow he will celebrate with his first-ever appearance on Conan as well as an album release show in L.A., with a New York release show to follow on the 24th. Last week Josh and I chatted about his new album and upcoming Conan debut, his artistic process, writing about family, lessons he’s learned, and what it’s like working on Last Week Tonight.

Nicole: First let’s talk about your Conan appearance coming up on Wednesday, March 23rd. Congratulations, that is really exciting! Is it going to be all-new material, stuff from your album, or both?

Josh: It’s all stuff from the album in kind of a juggled order. I’m definitely a little nervous because I don’t know how it will feel. I think once I start telling jokes, it’ll be fine, but there will be that moment before I say something where I kind of have to go, oh, what’s it gonna be like? And then ideally, once I start, I’ll be like, oh yeah, it’s like jokes. It’s been a long-term dream to have a set on late night, and I’m delighted to have this opportunity.

How did you get into writing and comedy? Why were you drawn to those things?

By the time Modern Seinfeld started at the end of 2012 (and that was definitely a helpful career thing!), I’d been doing standup for about eight years, and I’d been writing freelance professionally for a while as well. Co-writing that popular Twitter account definitely pushed what I could do to another little plateau — it was a helpful nudge in the right direction. I was able to start applying for TV writing jobs. I did a little work for Billy On the Street in the middle of 2013, which was really fun and helped buoy me – like, okay, I’m going in the right direction! And then I got hired for my digital job Last Week Tonight at the beginning of 2014, and became a staff writer after the first year.

The thing I liked about standup, immediately, is that it’s a way to write and perform and get immediate feedback.

I’ve always loved jokes. Even as a little kid, I remember ordering, like, dinosaur joke books from the Scholastic book club – I was always fascinated with how jokes work. And I really like standup as a fan. I think that’s not something everybody feels, but it’s something I have always enjoyed as a consumer of entertainment. I remember after my freshman year I started doing improv on campus, and a high school friend was doing standup, and our mutual friends were like, “Josh, why aren’t you doing standup, too? We know you want to do it.” So I kind of got bullied into my career by my close friends. My friend Dan encouraged me, and my friend Joe Smith (which I realize sounds like a fake name – like, “oh, Joe Smith, why won’t you use his REAL name? Is he the President now?”), who was the one doing comedy already, kind of showed me the ropes.

The thing I liked about standup, immediately, is that it’s a way to write and perform and get immediate feedback. I was a creative writing major, and I went into college thinking I’d write plays, and I left college thinking I was going to write humorous novels. But what I like about standup is that you don’t have to sit in a room every day and write something you can’t show to people until you have a whole 80,000-word document that’s ready to go. You can do little rewrites day to day, scrap something if it’s not working, but you haven’t spent years pouring all your hopes and dreams into one joke.


Tell us how your new album, “Physical Whisper,” came to be. 

I recorded an album in 2011 right before I moved to New York, and then started trying to build a new long set of standup material, which is my ongoing project outside of whatever I’m doing for work; there’s always constant standup tinkering going on. Then I wrote this book, You Blew It, with Joe Berkowitz, and that was really fun and exciting. There was a couple weeks of super-fun author events, but I couldn’t really go on a whole big book tour because I work during the day. And so I found that some of the excitement around having published a book evaporates very quickly. It’s such an extensive process from the writing and editing to promoting, and then the book exists…and then your life is kind of back to normal.

I knew I wanted a bigger-scale project than just doing standup or writing freelance pieces. And by the time the book came out, I was basically where I needed to be to record another album; I had another hour of material I felt I could bring out and record and be happy and proud to share. Which was a relief, because otherwise I don’t know what I would have done in terms of another project! When I was in college, I was taking classes, doing standup, teaching elementary-school Spanish — and then when I graduated, I was doing standup, teaching preschool, and tutoring. So I feel more comfortable when my time is rigorously scheduled and I have a big-picture project to look forward to.

On the album, there are sketches about your family, your dad, your grandmother. What does your family think of your comedy, and specifically their cameos in it? Do they listen to all your work and like, give you feedback when you write about them?

My parents and I are very close. My dad is both an intentionally funny person and occasionally an unintentionally funny person. So the joke about my dad wearing suspenders and sweatpants came out of a misunderstanding — I thought he was wearing sweatpants with belt loops (because those exist, apparently!), and I tweeted something about it, and my dad texted me – he texts me responses to my tweets all the time — “You know I would never wear sweatpants with belt loops, I wear suspenders with all my pants!” So that became the joke. He denies ever wearing suspenders with sweat pants, but it feels true.

When I gave my grandmother my first album, I gave it to her and said, “Nana, I want you to have this; I made it. I just want you to know, there’s some adult material. If you have any questions, never talk to me about them.” She got it, and was very cool in terms of my creative life, and always very supportive of it.

It’s a little weird to tell stories about people who have since passed away. But the story about being with my girlfriend, Maris, on the day of my grandmother’s funeral feels like a remembrance of her. My parents heard it and enjoyed it, and I think it’s respectful of that experience. I mean, to me it is objectively preposterous that she was cremated in a Tom Brady jersey, though that wasn’t her decision; it was a call made by family. That story is a bittersweet memory that still has funny elements, and it’s one I hope other people will relate to and even find joy in.

I really loved the stories about your family. I think even when the stories are positive and heartwarming, it can still be nerve-wracking writing about relatives. 

Definitely! I try to be respectful of that when I talk about romantic relationships, or family relationships. What do the people I care about think about what I’m saying, and what do they think about what the audience will think? ’Cause I’ll say any kind of garbage thing about myself onstage. But it’s different when it’s about someone else.

Do you think there’s a general personality trait that makes a person go into comedy and tell funny stories that are mostly about themselves?

I guess it’s kind of a generous narcissism — that’s what I feel about myself, anyway. Hopefully my troublingly inward focus can be applied to bring other people laughter. I guess I think a lot about myself and what happens to me, maybe more than I should, but if I can talk about me in a way that other people like and find funny, then I guess that’s a job and not a…pathology?

When I find that I keep thinking about something, my first impulse artistically is to try to make it funny. Anything we have a strong emotional response to can produce comedy, because it’s either ridiculous or intense – there’s always something worth describing.


Do you do a lot of revising and testing out work on friends and family?

Yes. Maris has a great ear for whether something tracks and makes sense comedically. I’ll run a lot of stuff by my friends Myq Kaplan and Robert Dean; we’ll have coffee and run jokes by each other. I don’t slip bits into conversations with people, but I will go, “hey, can I ask you, does this make sense?” Because of course it’s a terrible feeling to have someone say something to you and then you suddenly wonder, “Are you doing your act right now? I thought we were having lunch! I didn’t realize this was an intimate performance!”

Ultimately, of course, no matter how much testing you do or how much feedback you get from friends, it has to work for audiences; that’s the biggest sounding board.

Do you want to tell us about a favorite show, and then maybe a terrible show that you still learned something from?

My comedian brain, of course, is like, yes, the worst ones! Let’s talk about those!

I’ve done noon college gigs, in a cafeteria, at like 11:45 in the morning, because some schools sometimes have entertainment during lunch. I did one show that was so bad — they wanted me to be very clean, I was told going in: “Be easy. They’ve had bad experiences with comedians being demanding in the past.” Five minutes in I was like, are they gonna laugh, ever? It was 45 minutes of ruthless, brutal bombing. I felt like my whole career might be a mistake. Then I got offstage and the student events people were like, “PERFECT. We loved it.” And I realized that was because I did the thing they asked, and I didn’t act like I was bombing, I just gave a performance. Obviously it’s never the goal to have a bad show, but that one taught me so much about professionalism. People don’t want to hear “I don’t think this is going well.” You just have to give a performance with outward confidence, and people will walk away going, “Oh. That was a professional comedian we saw.”

As for a favorite show…there are so many fun shows. There are a lot of shows in New York, obviously – one of my favorites is Night Train. Getting to do that is always really fun. They did an hour of a standup showcase for a digital network that taped in December, and it was my first TV-esque taping. It was great to hang out backstage with so many people I admire: Wyatt Cenac hosted, of course, but then there was also Maeve Higgins, Hari Kondabolu, Scott Adsit, John Hodgman. To be in that company was wonderful. 

I’m such a fan of Last Week Tonight – it’s so sharp and always punches up and is weirdly compassionate and earnest and not jaded. What’s it like to work on the show? Is it pretty much your dream job?

It is a dream job for sure! When I started doing standup, I didn’t have any idea it would lead to television. I did move to New York with the idea that I would like to write for television, because it sounded fun, and it’s a job – you go to a place, you do a job, you get paid. I like that. It’s hard to make a career just doing standup.

I always loved The Daily Show and The Colbert Report, and I try to stay abreast of current events. I enjoy topical, issue-based comedy, so I fit in well at Last Week Tonight. Everyone on the show is really smart, and it’s a joy to be a part of something that I love and think I would enjoy even if I weren’t personally working on it. I take so much pleasure in the show and the people I work with – everyone is terrific, all the way through the show. It’s a great thrill to be a little part of it. 

Every piece we read about you is like “Josh is such a NICE GUY! He’s a nice guy in comedy!” which is 100% true, but do you ever get tired of that description? How else would you describe yourself?

I don’t get tired of it, because I think people mean it in a kind and loving way. But it’s also kind of funny, because when a comedian says, “oh, he’s a nice guy!” about another comedian, that usually means he’s not very funny. But I think people mean it kindly and I appreciate that.

I don’t think it’s necessarily a thorough description of my comedy, or that it’s unique that a comedian is nice — there are lots of wonderful people in comedy. I would describe my comedy less as “nice” and more as “friendly.” There’s a slight difference. With “nice” the connotation is “it’s fine, it’s good enough.” I try to make work that people in the audience aren’t gonna be bummed out hearing — they’ll say, oh, that was a good time! I like that guy.

So it’s really all about being liked?

Yeah, it is; again, it’s a pathology! It’s really about creating a feeling of warmth along with humor. That’s what I try to do.

Thank you so much for talking with me, and good luck with the album and your Conan appearance! Anything else you want to say to the people that we have not yet talked about?

I think this is fun — my album is coming out on cassette. All the cassettes come with digital download codes. I actually don’t have a CD player, and I know a lot of other people who don’t, either — I listen to everything digitally. But a cassette is a fun thing to be able to sell on the road — something for people who want a physical item or just really enjoy collecting outdated analog trinkets. So for my New York album release show on the 24th at the Jewish Museum, I bought 25 off-brand Walkmans, and the first 25 people to buy cassettes that night get a free off-brand Walkman to go with it!


Buy Josh Gondelman’s new album, Physical Whisper
Buy You Blew It, by Joe Berkowitz and Josh Gondelman

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