I dare you to describe Josh Gondelman as a comedian or a person without using the word “delightful.” It can’t be done. Josh takes the kind of gentle approach to his set, even when dealing with darker or edgier material, that can keep you comfortable in the audience whether you’re on a first date or taking out with your grandma. He is also unfailingly positive and supportive towards his fellow comedians and a true joy to spend time with off stage. So it’s fitting that his first album was called Everything’s The Best! And his new one (available March 18) is called Physical Whisper. Not surprisingly, the album is delightful and Josh is doing something very special with it. Besides releasing through the normal digital channels, he’s printing up cassettes. And if you’re thinking that you threw out the last thing you owned that could play those three apartments ago, Josh is giving away free Walkmans at his album release party March 24 at The Jewish Museum in NYC. Angelenos will get their chance to celebrate the day before at The Virgil after Josh finished filming his first Conan appearance.
Gondelman is a well known and beloved part of the New York City comedy scene, but he’s probably best known to everyone else as the hipster Republican in the excellent promo videos for the first season of Last Week Tonight with John Oliver.
Gondelman produced their digital content throughout the first season and got upped to full staff writer for the broadcast when season two began. “That’s a real privilege to get to work there. It’s all the same writers from the beginning and me. It’s a real thrill to get to be a part of a thing I am really proud to be associated with and to have a small part and how it turns out.”
In a way that’s the best kind of credit you can have, one that only applies to a few people. Not just from an exclusivity standpoint, but the point of a good intro is one that dials the audience into what they might know you from, who you might be, and that they might be interested in listening what you have to say.
It had started when my buddy Dan Boulger said, ‘You know, if they had cellphones, there would be no Seinfeld.’ Just every episode’s plot would be wiped out
Josh’s path into comedy is fittingly charming and sane. “I was like a kind of weird kid, not too weird, I was like the Screech of my high school. I was a generally well-liked nerd. That’s the thing about Screech, right? He was such a big doofus and he wasn’t even that smart, but he hung out exclusively with the most popular kids! I mean, that wasn’t what I was like, but I played sports enough and I was in plays and our school was small enough that there weren’t enough people to have stereotypes. Like, we had a goth cheerleader and there were athletes in the honors classes. A very weird thing in my high school was as a class officer you had to do two things – one was to plan the class dance or prom and the other one was to write a skit for the school variety show. I was the vice president my freshman year and I wrote the whole skit, so somehow on the strength of everyone in my class knowing I could write sketch comedy, I was class president the other three years. That’s like one of those Malcolm Gladwell things where of course you’re going to be a comedian when that’s the thing you’re rewarded for immediately and over and over again.”
“I did improv in college and then Joe Smith, I don’t feel bad saying his real name even though he doesn’t do comedy anymore because with a name like that nobody’s ever going to find him. But so Joe was doing stand-up and all our mutual friends were like, ‘Joe’s doing it, why don’t you do it?’ And so I got badgered into open mikes. It was great starting out there because when I started, there was every different kind of show. There were little clubs where you could work with people from Boston and occasional outside headliners, then there was road stuff that wasn’t that far and then there were the weird little alt shows. When I started, there was The Comedy Connection in Faneuil Hall and I was just starting to get in there when it closed in 2008 and then there was that dip for a little while and then Laugh Boston opened up a few years ago.”
“I think one of the things that precipitated my move to New York was that with The Comedy Connection, there was this idea that ‘Oh, someone is gonna come through here and I’ll open for him or her and they’ll take me away from all this! Someone’s gonna come see me and they’re gonna introduce me to show business!’’ And then that died in 2008. It just didn’t feel like much room to grow and I find it hard to motivate myself when I don’t have a goal in mind. I think when you’re in another city, other than New York or Los Angeles, that’s just how you see it happen. Like, Joe List, when I first started was doing great and then he started opening for Nick DiPaolo on the road and I saw, ‘oh, that’s a way out.’ Or Myq Kaplan, people would see him in Boston and take him on the road and he had a college agent who would get him gigs at schools and I thought, ‘ok, that’s a way out.’ All that stuff helped me see what existed and it felt like none of that existed for me at that time in that place.”
“It helped that I had a little nest of people I already knew to land in when I moved here. Mike Lawrence, Dan St Germain, Mark Normand and Matt Ruby had all come through Boston and were very nice to me when I first moved here. And then the guys who were from Boston and would come back occasionally, like Myq, Jon Fisch, Gary Gulman, it just felt nicer knowing that they were here. But definitively my first six months of New York comedy were harder than any six months in my entire life. I was just going out to open mics and even my good material would eat shit and my new material is even worse. I was trying to figure out, ‘Do I just not know how to do this? I thought I did but maybe not.’”
Josh certainly proved he actually knew what he was doing. Through a combination of hard work, steady improvement and just showing up, he came to be a staple of NYC’s independent shows. It didn’t hurt that he’s such a pleasure to be around, either. “A lot of it comes naturally, I give a lot of credit to my parents for being generally wonderful people and I’ve definitely had low times but I’ve never had a life-shattering tragedy strike me. So I’m just wired to appreciate good things and work through bad things. I think generosity is one thing I do have to remind myself to do, I remember that a lot of the good things that happened to me in my life are because someone else did something generous for me. So I try to remind myself to look for those same opportunities to be generous to people I like and believe in.”
“I think comedians are a better bunch of people than we are presented as, for sure. I just think we’re more outwardly expressive of grievances and hardship than other groups. It would not be rewarded as an accountant or an actuary to be super open about the kind of darkness Maria Bamford brings to her comedy and we all benefit from in a delightful way. You definitely wouldn’t want that from your pediatrician.”
Since Josh brings so much joy to others, we capped of the interview by asking what makes him happy. Not surprisingly, they are some of the nicest and least selfish answers anyone could imagine.