Meet Me In New York: Josh Gondelman

(Photo of Josh Gondelman by Mindy Tucker, August 2015)

What do they say about New York City: There are eight million stories, and sometimes it seems as though eight million of the people telling them think they’re comedians? No, that’s not it. It is a fact, though, that America’s biggest city is also its biggest comedy mecca. Hollywood may be Hollywood, but New York City is where comedians are born funny, become funny or arrive to thrust their funny upon us. I think we should meet some of these people. This is a recurring feature, a mini-profile of newcomers, up-and-comers and overcomers of New York’s vibrant comedy scene. It’s called Meet Me In New York.

Josh Gondelman was a fresh-faced Brandeis University student when I first spotted him, and running an open mic in Somerville, Mass., with Myq Kaplan when I made the move to New York City in 2007. Gondelman wouldn’t follow for another four years, but he has more than caught up with me, Myq and everyone else. A win in the Laughing Skull Comedy Festival that earned him a year’s worth of road work. A Modern Seinfeld Twitter tribute account broke big and proved he knew today’s New York City. An online assignment for HBO’s Last Week Tonight with John Oliver that begat a writing job on the weekly show. And now a book, You Blew It!, co-written with Joe Berkowitz.

Gondelman met up with me outside of his Last Week Tonight offices near Columbus Circle to hop on a subway train to Brooklyn for a gig he had that night. You can hear our Meet Me In New York in full by investing in The Comic’s Comic as a paid subscriber via Patreon. So what are you waiting for? Please invest and reap the benefits!

Name: Josh Gondelman
Arrival Date: July 31, 2011
Arrived From: Somerville, Mass.
When and where was the first time you performed comedy?

“The first time I did stand-up was probably on campus at Brandeis. And then I started in the city as soon as that – so that was once during my second semester freshman year. And then I started, I think really doing it seriously at Dick Doherty’s Beantown Comedy Vault on a Sunday night in July of 2004.”

What was your best credit before moving here?

“My best credit was probably that I’d won the Laughing Skull Comedy Festival in 2010. I won the first one. It was a comedy competition and it was really fun, was very helpful to getting me out on the road a little bit more. Stuff like that. Yeah, it was great.”

Why did you pick New York over Los Angeles or anywhere else?

“My family’s on the East Coast, so I like to be close to them. That was nice. And I knew I had friends here. There was like a nice kind of Boston lineage here that I felt comfortable in and excited to try to be a part of, and it’s very nice. There’s a lot of great Boston comics – from Myq Kaplan, Gary Gulman, Jon Fisch, the ones that aren’t Jewish, also. There’s a lot. So it felt nice to land that way.”

How long did it take to get your first paid gig in NYC after moving here?

“I think it was a few months, and it was like – it was either, and I was thinking about this, because this is one of your regular questions – and it was either a spot opening for Myq Kaplan at Caroline’s on like a late Thursday show where I just bombed my face off for 15 minutes. Or it was a show at Karma Lounge that Jay Welch and Nick Cobb used to host together called Arms & Hearts.” And that paid? “Yeah! I think it was like $20 for a spot on a Friday or Saturday. It was very nice. It was thrilling!”

How is the comedy scene better/worse/different from where you lived before?

“It’s bigger and there’s more opportunity. There’s just so much more. It’s vast. And you get to see so many more comics at the top of their game doing different things. In Boston there are lots of great comedians to watch. But here in New York, the people you would have to wait for them to come through maybe once a year, you get to see – if you want – a couple of times in a week.” Was that the Boston scene circa 2011 or Boston scene now? “I think both. Laugh Boston is bringing in people in kind of a similar way that the Comedy Connection was doing when I started, where I could go and watch a real strong national act. So this is just what there is here at comedy clubs.”

What’s an “only in New York” experience mean to you? Do you have one? Other than talking to me on a subway car.

“Well, I guess a lot of cities have subways. I’m trying to think of a great – I don’t know. Hmmm. I guess. I’ve slept in a bedroom the size of a bed. That’s an only in New York experience.” How do you describe the craziness of New York to people? “I guess it’s just always happening. Like, anything that could be happening anywhere else is always happening here on top of something else. So, that to me, is the defining feature of New York as a city.” But you haven’t had a Pizza Rat experience? “I mean, I feel like Pizza Rat was kind of overrated. I think in New York, you can see a rat eating food of any culture, and that’s the beauty of it. Or the disgusting part of it.”

What tip would you give any comedian who moves here?

“I would say the first few months, the first six months for me were super super hard. It felt bad, and I didn’t feel like I’d ever done comedy before. And it just like was a real shock to the system. It just gets better. Which at this point is a cliché hackneyed thing to say about any situation, right? After Dan Savage made that such a powerful statement. But it does. It gets better comedically. You start to feel more like yourself, you learn what you’re doing, and you fit into the scene. But know it’s going to be hard. I moved under pretty good circumstances and it was a real tough six months. My first ‘only in New York’ moment was, the first show I was booked on when I got here – which was Harrison Greenbaum and Sam Morril’s show, at Ninth Street and Second Avenue. I was onstage and Jim Gaffigan dropped in right after me, and the first thing he said was in reference to the last joke that I did. It was about the team from Mighty Ducks 2, the bad guy team being a bunch of hulking Scandinavian Holocaust deniers? And he comes on and says something like, ‘You know, it’s hard for a guy who looks like me to come onstage after you’ve all just heard the phrase hulking Scandinavian Holocaust deniers.’ And it was just like. I thought, ‘Oh. That was so fun that that happened. Not that he was like, that’s a good joke, but just that that experience happened. I didn’t even know he was in the room. He heard something I said, and then was part of the fabric of the comedy that night. So that was really exciting and pretty neat.”

You’ve done some pretty exciting and neat things yourself: The popular Seinfeld parody account on Twitter; you’ve written a new book; and you’re a writer on John Oliver’s show, Last Week Tonight on HBO. So. Where do you see yourself in five years?

“Oh gosh. I really love my job, and hope that it continues to exist for me. And then I also would like to do more outside projects that are self-directed and self-guided. Like another book. Maybe of more personal stuff. Because this book, I’m very excited about and happy that it’s out, and it was a nice way to start fake advice topic – it’s about how to make your life worse. So that’s pretty fun! But it’ll be nice to put more of myself into the next thing, I think. And then I guess being able to work a little more steadily on the road in the weeks between work, which would be really fun. And to get to play fun comedy clubs and things like that. So very much the same, but with slightly more creative control, increasingly more creative control. Wait. That’s not even fair! I don’t think creative control. I think meaning being a little more of a draw, and less of, here’s the guy behind this book that’s funny – that co-wrote with my friend, Joe Berkowitz. But to be like, oh, I got that book because I like this guy and it’s his thing. Which is exciting. That’s what I’m hoping for.”

Let’s check back in 2020, then!

Listen to this Meet Me In New York by investing in The Comic’s Comic as a paid subscriber via Patreon.

Please buy his new book, You Blew It! It’s available now wherever you buy books. His “Worst Book Launch Party Ever” happens tonight at The Powerhouse Arena in Dumbo, Brooklyn, with guest readers and storytellers including Louis Peitzman, Aparna Nancherla, Heben Nigatu and Bob Powers. He’ll also do a book event on Oct. 21, 2015, in Brookline, Mass.

You also can see Gondelman performing onscreen sometimes with Last Week Tonight or at shows near you.

Which NYC comedian would you like to see me style and profile next for Meet Me In New York? Send your nominations to: thecomicscomic AT gmail DOT com

Sean L. McCarthy

Editor and publisher since 2007, when he was named New York's Funniest Reporter. Former newspaper reporter at the New York Daily News, Boston Herald and smaller dailies and community papers across America. Loves comedy so much he founded this site.

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