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Rooftop Comedy Productions is proud to release Everything’s the Best!, the debut album from Josh Gondelman. Josh established himself in the Boston comedy scene, winning over crowds—preschool students and club crowds alike—with his musings on dating, children, his years as a teacher, and more. You’ll be hard-pressed to find a comic as grounded in his awkward dorkiness as Josh, but that just makes him that much funnier. Rooftop recently chatted with Josh to discuss performing for preschool teachers, channeling insecurities into a confident, hilarious act, and sharing the stage with carrying the Boston comedy mantle to New York.

Rooftop Comedy: You recorded Everything’s the Best! in Boston at Mottley’s, right before you made the move to New York.

Josh Gondelman: I did. I wanted to have all my creative stuff to do with it done by the time I left Boston.

RT: Was it a packed club with all your loyal friends and family?

JG: Yeah it was great. It was really nice. I had some childhood friends who came and a lot of comedians— the Boston scene is really supportive of our own. So I felt it was a really warm send-off. And my family was there. It was great! We had two sold out shows, even during the Stanley Cup finals.

RT: Oh wow—not exactly the easiest act to share the stage with.

JG: In Boston, sports can ruin comedy. It’s really nuts. When the Red Sox won the first World Series, everyone was really psyched. Then in 2007, it was like “Oh, this is really great”, but at the same time, the longer they string this along, the more shows will get cancelled because no one is leaving the house.

RT: I imagine the Boston comedy community as one big, loving family, with Joe List and Kelly MacFarland cheering you along at your show.

JG: It’s really great. Kelly and Joe both recorded with Rooftop, so I called them both to be like, “Hey, would you recommend this? Also, do you think I should do this?” They were both like, “Yeah, man. Go for it. Rooftop’s great; you’re great”, which is very sweet of them to say. When I got to New York, there was a really nice nest of Boston people that I know through generations, like Myq Kaplan, Dan Hirshon, Joe List, Gary Gulman, Jon Fisch, Micah Sherman, so many from the improv and sketch world. It was so nice and comforting to come and in my first week, I ran into a lot of people that I knew, but probably four or five people that I knew that were Boston comics. We live in New York. We do comedy in New York, but we came up in Boston. It’s a lot of loyalty and a lot of pride.

RT: Your comedy draws a lot from your personal life and experiences as a preschool teacher. Do you like to blend these various circles and bring them to your shows?

JG: The preschool teachers, actually, that I used to work with were the best crowds when they would come. They love the preschool material and it was almost like when a group of moms go out or a group of people that don’t get out much together all go out together and so they would just be out of their mind with excitement, just cheering for everyone on the show. [Other comics] would be like, “Who’s this whole row of 28-year old women?” And I’d be like, “Oh, that’s my co-workers back when I used to teach”. They’re super nice and my old co-teacher called me, because I used to write the holiday play for the kids every year and she was like, “I know you don’t work here, but will you still write the holiday play and come watch us do it?” I would always direct it and I would be the guy onstage, telling the kids where to go, but this year they’re going to do it without me, but they still asked me to write it, which is really sweet and funny. I hope they don’t screw it up. I kind of have a reputation.

RT: Do you miss your preschool students?

JG: I do. I’m really happy to have more flexibility in my day and be able to travel more and write more, but I miss having something that I got to do every day that made me feel like a valuable member of society. I would always leave school and be like, “Man, that was a rough day. One kid was crying because his dad was out of town. Another kid pooped on the floor, but I feel like I made someone’s life better today”. I miss that. It’s a very delightful way—even when I come back to visit, because I go back to Boston, if I have time, I’ll drop in and just say hello to my old boss and the little kids. There are kids there that I know from when they were babies and they always go crazy and it’s super sweet.

RT: On stage, you mix self-deprecation, warmth, and wit. Has this always been your comedic inkling or did it evolve overtime?

JG: When I started, the self-deprecation was a lot more down. It was a lot more “Aww”. Now, I’m a very comfortable person in general. I’m kind of a weirdo, but I’m very comfortable with it. I’m very at ease most of the time. I’m not anxious, socially. I feel comfortable on stage. It’s easier to just kind of be a person and write about who I am as a person. There are things that I say that are kind of self-deprecating, but I feel like they’re not in a way like, “I suck”. I always try to do it in a way like, “I’m not good at this. I wish I were better at this. I don’t understand this. I’m fascinated by this because it goes over my head”. When the jokes are good, and I hope they are, it keeps the audience more on your side. I started when I was young. I started when I was 19 and I wasn’t as confident as I am now. So even though I’m still kind of a dork, I’m a very comfortable, at-ease dork. I feel like that puts the audience at ease.

RT: It’s also easy to relate to.

JG: Thank you. It’s not like the heavy Richard Lewis anxiety and sense of discomfort. It’s not like Louis C.K. self-loathing. Things in my life are very happy and very fortunate and where there are little creases or little wrinkles, I try to dig into those and find the little weird things that are relatable to other people.

RT: Anything else you want people to know about Everything’s the Best!?

JG: I’m just really excited for the album to be out and to have this hour of comedy out for people to hear. I have my hard copy CDs and I’ve just been handing them to people I see and been like, “I hope you like it!” Then I run away. Obviously, there’s the idea of selling a CD to make money on the road, and I’m planning on doing that, but I’m just very hopeful that people enjoy it. I don’t think this project is going to catapult me to superstardom, but I’m just really excited to have people react to it and hopefully to have it be something that they enjoy.

Everything’s the Best! is now available on iTunes, Amazon, and the Rooftop Comedy shop (where you can listen to a free sample track!). Josh will be performing at the Afterlife Comedy Show, Nov 18th at the Sidewalk Café in NYC.