J: How did you get to the point where you were talking to HBO and developing pilots?
BD: I was working at Second City in Chicago and the Aspen people used to just come there as one of their stops, but for the past few years they’ve been just calling and asking who’s there doing what kinds of material. I had done several one person shows in Chicago so the Second City people told them that one of their cast did solo work, and they came, and my friend Matt, and I, and a few other people auditioned in Chicago. They had a callback in New York out of 120 people who auditioned. I got to Aspen and did a 23-minute version of my one-person show there, and also did [Second City alumnus] Catherine O’Hara’s midnight lounge show, and the world opened up to me from that.

Coming from Second City, it’s a very big deal to some people, but you make $450 a week and the industry part of things doesn’t really exist in the Chicago world. So this was my first introduction to agents, managers and development deals, and the network or a studio, and what all that was. I had to learn it as I went, and it was a sudden onslaught of being wined and dined by all these big agencies and management companies. Everyone was aggressively courting me and I didn’t know what was going on. I had to really take my time and figure out what the right questions were to ask and really think about what I wanted to do, and what I didn’t want to do -- and who to set myself up with who would best allow me to do what I wanted to do. It was a set of questions I never really had to ask before because those options weren’t really out there.

At Second City, you could either go to Saturday Night Live or Mad TV and work as a writer and performer, but you don’t know anything about doing a development deal with a studio or setting up a pilot. That world doesn’t really infiltrate the Second City world very much. I had to learn it and do it at the same time. I was really lucky and ended up with some really great people, and met great people who weren’t managers or agents who I could trust to help me through that whole process. There were three or four months right after Aspen where it was insane. It was like Pinocchio when the shady actors are trying to coerce him into doing all the wrong things. But the good news was I was in a position to take my time and make some good decisions. That was how everything exploded. Before that I was working at Second City, doing six shows a week and making $500 a week and totally happy with that.

J: When you came to New York, how was that part of figuring out what you wanted to do?
BD: I always wanted to move to New York and that gave me the opportunity and the money. I moved to New York right after I did the deal with HBO, because I always wanted to be here, and it finally made sense for me to be here and I finally could afford to be here. I wanted to come to New York, and have a dog, and those things became possible. I’ve been here for a year and a half or so and the bulk of that time was waiting for this deal to happen or not. But now that’s over, I’m a lot more motivated and excited to get onto whatever’s next.

J: How do the improv and solo shows that you’ve been doing here fuel everything else?
BD: I don’t know; I’ve struggled a little bit to figure out where I fit in this community. A lot of people come from Chicago and move here, and I know a lot of them, which is nice because there’s a lot of familiar and friendly faces around. But I didn’t spend 10 years in Chicago improvising and was never really known as an improviser. So I was never really comfortable as an improviser, even when I was with Second City and was playing with a lot of people who were so good and that was just not my thing. So it took me a long time here to start playing and improvising and having fun with that.

I came here with my one-person show -- I came and did my show, and I left, but I wasn’t and still aren’t really a part of that Upright Citizens Brigade community, and a lot of people who come from Chicago have been improvising for a very long time and have a whole set of friends here. They get jobs on SNL, Colbert Report or The Daily Show and have more of that social element built in, but I’ve always done solo stuff. When I moved here, I was doing solo stuff, so it was a solo kind of feeling. Because I was working alone, I wasn’t going to an office every day and being around a lot of people, so it’s only really been very recently that I’ve started playing more, improvising more and getting out there more. I’m surrounded by all these people and thing, ‘Wow, I really like that person, I wish I knew them and we worked together.’ I’m just now starting to take that step.

Part of it is, doing a one-person show, you sort of become a one-person show. But I started playing with people I really like and admire from Chicago. Writing a new one-person show isn’t quite as urgent as learning other things like writing a half-hour comedy and understanding that world. It would be naïve for me to say I have experience in television, but I feel better prepared to go out as a writer and pitch a pilot.

J: Could you cite a best and worst performing experience?
BD: I did a musical number [at Aspen] that I was told by some people was a very bad and very risky idea that was nearly a career-killer. It ended up being something that clinched a lot of opportunities for me. The running order was Eugene Levy, Catherine O’Hara, Cheech & Chong, me (laughs), and then later in the show, Jeff Garlin and Paula Poundstone. Being in the green room with all those people and coming up big knowing that I had just killed was one of the most exciting things that had ever happened to me --making my mentors laugh and impressing them. The show was very much about mixing in up and comers with the famous people at the festival. My song was very much about ‘what the fuck am I doing in this show?’ That was a major turning point for me, not only in performance, but in realizing what’s important to me. Blowing these people away and feeling like I could do a show with Catherine O’Hara. The whole experience was a life changer.

Months and months later, GO NYC magazine had a party for their “100 Women We Love” issue at Crobar, and it was a great forum for a band or a hip-hop act, but not for comedy. It was just fucking awful. But I’ve been in shitty performance situations before and you just keep going and say to yourself, well you’re not wrong to be doing the material you’re doing. In that situation it was just the absolute worst venue decision possible. From a promotion point of view, you don’t have a comedian do stuff if you have a band. I was up there doing my Dr. Seuss lesbian thing, which is my lesbian bit, and everyone wanted to dance and drink and make out, and they just hated it. I’ve never felt so much wrath and venom from, like, 4,000 lesbians. I thought, ‘Wait a minute, these are my people, this is my audience.’ But I just chalked it up to wrong place, wrong time. Had it happened three years ago, I would have cried for a week. But I just got off and danced and drank. I had a woman in the front just screaming at me to get off and that I was ruining everyone’s life. Had I been in that audience and someone was trying to engage my attention with that kind of material, I probably would have thought, ‘dude, not here.’ I totally understood it.

J: Would you do anything for them again?
BD: I know the people and they’re very nice. They were appreciative. … They just didn’t realize. I had a rough year at Boom Chicago [an Amsterdam theater featuring ex-pats from the Chicago improv scene]. Seth Meyers worked there, and half the cast of Mad TV, and Jason Sudeikis. It’s become a major feeder for Mad TV and SNL. But I wasn’t ready for that kind of experience and spiraled downward to a bad place. Now of course I can laugh about it, but at the time it was murder. I took so many drugs and lost my mind, because I was 20 and living in Amsterdam and I had never really done that before, never lost control. And I couldn’t imagine why I was having a bad time there and got a bad reputation. Until then I had always been the funniest, and most talented, and the person everyone wanted to do a scene. Suddenly I was the last person anyone wanted to play with, and it was really hard. So to make it better, I would do mushrooms by myself. Performance wise it was like being the kid on the soccer team who can’t walk properly.

J: Like being the kid who gets two minutes at the end of the game.
BD: But not even in an endearing way, like [the movie] “Lucas.” I would have liked to be [even that]. That was really the first time I experienced that. It took me several years to pull myself back together from that, but when I did, it turned out to be one of the most positive things to ever happen to me because I got through it. I just felt so shitty after shows there because I had no confidence, no personal confidence. I was a fucking wreck. I would get offstage and cry. It was just terrible.

But originally, I went to summer camp as a kid and started doing sketch comedy … and all the things that made me weird, different and funny before were celebrated, valued and encouraged, so I was really lucky in that way.