By Cesareo Contreras
You’ve been to Framingham State previously, right?
This is my third time, yeah. I always like the crowds here. The audiences are great. I do like to tease the audience, as you saw. That’s all part of it. I’m really trying to entertain them in that as well. It might sound like I’m saying, “You guys are too sensitive,” but really, even in the saying, “You guys are sensitive,” I’m trying to make them laugh. You know what I mean? But it is interesting sometimes to watch what a crowd will think is over the line. So you’re not swearing or saying anything hurtful, but tonight people didn’t seem to like I was making fun of the name Leonard Kravitz. That almost made me feel a little like a bully or whatever. When I’m like, no, I’m not being a bully, I’m just being silly. But then I start to get it. Am I being a bully? So then you just start doing different material. But the crowd was amazing. For a bunch of kids I’m assuming don’t go see comedy every weekend, they really knew how to laugh. They
knew how to find the pacing, the applause. They were paying attention and they would play if I wanted to play, like Hannah and the guy in the back. I was really having a lot of fun. It didn’t feel like work at all. I love Framingham State. I’ll always come back. It’s fun for me.
What inspired you to go into comedy? What were some of your inspirations?
Seinfeld has a funny quote where he says, “If people think they can do it, they will do it.” It’s like one of those things. I started to get the feeling that I might be able to do it just because I like speaking in front of people and I like trying to entertain people. So then from that you just sort of start trying your hand at open mics and stuff and you get those first kind of laughs and it becomes, a little bit, in a good way, a compulsion, like you really want to keep doing it. It feels really good. It’s like a way of making everyone happy. It’s almost a peace-making quality for a person.
When did you start doing comedy?
It was 2001. I was in Boston. There was this place called the Hong Kong which is still there, which is one of the first places I performed, and there was a place called the Comedy Connection, which was in Faneuil Hall. They had an open mic as well. And I did that maybe four or five times, and I did the Hong Kong once or twice and then I was also doing improv in college. I started an improv team and then ... right around sophomore year, it all started to come together.
You’ve been doing your podcast since 2011 and you’ve had a variety of guests on. Have you
learned anything from that experience that you didn’t think you were going to learn?
I’m fortunate I’ve set up this way for me to have these conversations with some of my heroes. So it’s taught me everything. It’s been a real way for me to further my education and it’s really helped me understand who I am, what I believe, what I like and what I don’t like. Glen Hansard, the musician, just did it. And being able to talk about the mix between confidence and humility that every creative person needs to have. You need to have some degree of ‘I deserve this. I deserve to be on stage.’ That’s the confident part. But then you also have to have something that balances that out inside of you, that you want to prove that you can be a good entertainer, but there’s a little bit of doubt in there. ... For me, it’s usually some sort of self doubt that makes you human.
You recently did one with Pete Davidson of SNL and one with Weird Al. Is there a certain type of guest you especially like to talk to?
Yeah, some of my favorite episodes aren’t necessarily super famous people, but they’re amazing. Like Moshe Kasher, the second time he came on was one of my favorites. ... Josh Rubin is one of my favorites, Ray Romano, Judd Apatow was great, Noel Gallagher from Oasis was really fun. I was glad he did it. It’s always different, man. ... For the most part, what I’ve learned is that if you get someone in a room, just you and them, and you ask and genuinely care about them, they’ll probably play ball, they’ll give you a good conversation.
So I know you’re doing an HBO show directed by Judd Apatow. Can you talk a little about that?
Yeah, it’s fun, man. Judd had always been a hero of mine. I love his work. ... Well, he actually did my podcast before my talk show. So he was gracious enough to come on a live podcast we did in Austin and that’s how we met. Then we kind of lightly stayed in touch. Not really anything serious, but then, when I had my talk show, ... my manager, who has a lot do with this, put us in touch and asked him if he would do a segment with us. I got to go in his office and we acted together, so we did this little skit and it was really fun. We got along well. We made each other laugh. ... Around six months later, I was at another network pitching a show, a new show. And I knew it wasn’t really what I wanted to do. I was kind of pitching them what I thought they wanted, instead of what I knew I wanted to do. And then I got in my car, I was a little bit frustrated and just in that moment came up with the idea of a show about a guy
who gets divorced and has to stay with his friends. Like, every episode he’s staying with another guy. All my friends are comedians, so it would be like, whoever we could get. My friends in my real divorce, it was like Kumail and TJ Miller, John Mulaney ... These were the people that I called when I got a divorce.
So I was like, what an interesting kind of idea for a show – I lived it. Why not just make a dramatization of that? And then I was like, well, who does that sound right for? Well, Judd Apatow. That sounds like his sort of thing. He does that heartfelt funny. He likes the world of comedy. ... I flew to New York and got in touch with his assistant. ... We tried to set up a meeting, he was doing a movie. They were like, you can sit down with him for 15 minutes at like 7 a.m. or something on the set of the movie. I went in, we talked for ten minutes and then I pitched him the idea in the last five and it kind of kept going from there.