By Jason Pomietlasz

Josh Gondelman is set to perform two shows at Helium Comedy Club in Buffalo on what some people call the most romantic day of the year and others just refer to as Friday. He was kind enough to take the time to answer a few questions. Not every comic I contact for this responds, so it seems one’s coolness may directly correlate to how they respond to emails!

Gondelman recently worked as the head writer and an executive producer for Desus & Mero on Showtime. He contributed to the final season of The Marvelous Mrs. Maisel and, prior to that, he spent five years at Last Week Tonight with John Oliver. Visit www.Joshgondelman.com for anything else you would like to know about Gondelman.

You’re from Massachusetts and started doing stand up in Boston which has produced many great, but more on the, let’s say, gruff side comics. How did you manage to keep your niceness while dealing with Bostonians on the open mic scene? 

Okay, I love starting off here! I do have a pretty gentle energy onstage (and, let’s be honest, offstage). It took me a while to tap into that as a performer, just as it can take anyone a while to find their voice. And at first it was a little tricky to stay on top of a Boston audience, which I’ve always felt was like being on a pirate ship that wanted you to be their captain, but were more than ready to throw you overboard if you weren’t a capable leader. But once I figured myself out onstage, it felt good to be a change of pace, and I think that crowds appreciate when you bring something unexpected to the texture of a show. Even pirate crowds.

I’ve often found other comics to be nicer than advertised, socially. In Boston and then in New York City once I moved, there was a little period of proving that I was serious and was going to keep showing up, and then it was mostly pretty smooth. A few months into doing open mics, a more experienced comedian came over to me and said: “You’re a comic, right?” And I was so happy to be recognized as part of the scene. So, way too eager. I was like: “Yeah!” And he goes: “Then give me a pen.” And that still felt good, to be known enough to be bullied a little. 

Obviously this isn’t everyone’s experience, and I think I probably benefited from being a dude in what was a very dude-heavy scene at the time. But I think in a perfect world, a little light needling like that could feel fun and inclusive for everyone, rather than a way of keeping some people out of the boys club. (I think/hope things are getting better than they were when I started one million years ago!)

If you were a professional basketball player what team would you play for and why? Also, do you have a dream squad of famous people you would like to play with on a team? 

Oh geez. I mean, I’m a huge Celtics fan, but if I’m being remotely honest, my professional basketball dreams died when my skills and height leveled off in tenth grade. I did pretty well on the court at summer camp, so I think my best shot at going pro might have been in the 1920s in some kind of short-lived all-Jewish league where everyone is 5-foot-11 or shorter. I’m imagining a time when Jews were not allowed to play in the bigger professional outfits, as opposed to now when we mostly don’t make it to the league on our own merits.

I used to think it would be fun to play in the All-Star celebrity game, but now I’m just terrified of the embarrassment of finally getting famous enough to be invited, only to get dunked on by a 20-year-old Twitch streamer with a name like MrTheManThatsHim.

You are an Emmy award winning writer. Did little Josh ever imagine that would happen to adult Josh and do you have to adjust your writing style when writing for shows like “Last Week Tonight” compared to writing your own comedy?

I absolutely never imagined winning an Emmy as a kid, and even when I started doing standup it wasn’t on my radar. I really love writing and telling jokes, and it’s so much fun to be a part of a big wonderful team like the Last Week Tonight staff (and the Desus & Mero staff, and the Maisel staff). As a side effect of pursuing a life of perpetual goofing around, I have a shelf full of terrifyingly-heavy golden trophies, which was extremely unexpected.

My sense of humor has a lot of overlap with John Oliver’s, I think, so the big challenge was adapting that sensibility to write about things like immigration court and civil asset forfeiture, which aren’t subjects I gravitate towards in my own work, believe it or not.

It seems like podcasting is being depicted as a lucrative and easy career in movies and TV these days. What’s your view on them and do you have a favorite podcast to listen to or be on? 

As someone who had a podcast for a while that I really enjoyed doing but never made me money on, I will say I think it’s deceptively tricky to make it big in that world. 

Last year I had the best time on the Hey Riddle Riddle podcast as well as Welcome to Talk Town, which are both so fun and silly. And as a listener, I’ve been really into Ruined, Blank Check, The Flop House, 16th Minute and Doughboys. Plus a number of NBA/WNBA podcasts that I cannot justify from a time-management standpoint.

What’s the best advice you have received in comedy? 

Years and years ago I heard Mike Birbiglia say something like … when you set out to write a bit, write it the way that you really want to sound. And if the audience isn’t on board, take a step towards them and extend your hand to invite them towards you (metaphorically, not physically). If it still isn’t connecting, it’s up to you to decide how many steps you’re willing to take towards the audience to get this idea across without just pandering to them.

I think about that all the time because it has always felt like a great way to balance being a (sorry, sorry) artist while working in a medium that requires a specific reaction at regular intervals.

What is the best moment you’ve had on stage and what has been your biggest disappointment, career wise?

In 2016, I got to do a set on Conan (the show), which was my first late night appearance. It went well enough to be a relief when it was over. Conan (the person) invited me over to the couch for the final segment, and after he said goodnight to the audience, he turned to me as the credits rolled and whispered: “You know we can’t use any of that, right? We’ve got to air an old episode of Get Smart or something.” It was so delightful to me that Conan thought it went well enough that he could tease me and I would know he was joking. You can see a theme developing here, I imagine.

In terms of disappointments, this may sound bleak, but there are just so many setbacks you face all the time working in this field, and I try to feel the sting of them, and then let go as much as possible. I think there’s something nice about being able to look back fondly at good times from the past, while being able to let the rough times fade away a little bit. Especially since I’ve been really fortunate overall, and so many times when I’ve taken a step back, I’ve been able to take two steps forward afterwards. I’d feel a little petty still ruminating on festivals I didn’t get booked for in 2010 or whatever.

Jason Pomietlasz is a writer, aspiring comedian and covers comedy for The Buffalo Hive.