Jocular stand-up comedian Demetri Martin looks for laughs at the Boulder Theater on Thursday, November 16, two days prior to filming a one-hour special for Comedy Central; for more on the date, click here to see the item in the latest Westword. But the former staff writer for Conan O'Brien and current Daily Show regular had a lot more to say than would fit on a single page. In the Q&A that follows, Martin talks about temp jobs, a long-ago attempt to turn him into an Air Force recruit and the pain of being rejected by his own mother and grandmother.

Westword (Adam Cayton-Holland): Where are you at right now?

Demetri Martin: Chicago.

WW: How's the tour going?

DM: It's going pretty well. The crowd's are really nice. It's a little tiring sometimes, but I'm enjoying it.

WW: Are you pre-show right now?

DM: Yeah. I'm doing a show at the Vic Theatre here in Chicago tonight.

WW: Is this the biggest tour you've ever done?

DM: Yeah. I've never really done an official tour. I've done some shows here and there on the road in the past, but I've never really done a tour.

WW: Are you a fan of touring?

DM: I like it. I've got friends on this tour.

WW: Who are you traveling with?

DM: Leo Allen, another comic and a good friend of mine. And my friend David O'Doherty. He's from Ireland and tonight is the first show he will be doing because his tour was held up for some reason this whole time so he has missed fourteen shows or something like that. I met him in 2003 at the Edinburgh Fringe Festival.

WW: I was looking at your MySpace page before this interview and it seems like you have some increasingly devoted fans. Have there been any sort of uncomfortable, stalker moments on this tour?

DM: No, everyone has been really cool. I think that has been the best part of the tour: I stay after the shows and hang out and talk to people. That has been the most encouraging thing, that a lot of people that come out to the show are just younger versions of me and my friends. It's a nice feeling when you send something out in the world and it kind of comes back to you.

WW: From your schedule, it looks like you work four or five days in a row and then you have a couple days off. What do you do with those days off?

DM: The last break, I was in Columbus, Ohio, doing Daily Show stuff -- the "Midterm Midtacular." I think it was on last night. I was there for my break doing this piece and then we put it on the air. I did get to go back to New York for one of the breaks and the next break I'm going to Austin to scout the venue for my special.

WW: Is this tour gearing up for that one-hour special?

DM: It's a Comedy Central thing. It was kind of offered to me... I'm sorry, it was offered to me. I wanted to do one a little bit later. I'm not in a rush to put a lot of stuff on TV. I don't really like doing it that way, but this was kind of a window that was available so I said okay, yeah I'll do it. It's kind of nice and it makes me work a little harder to get everything together and as good as it can be.

WW: And are you writing and trying out new material as the tour progresses?

DM: Yeah. Which is what I like.

WW: I read in a previous interview that you are finding out on this tour that people do know you -- but can you still be a little anonymous?

DM: If it's anything it's just The Daily Show. It's a real little niche, it's not a giant thing.

WW: Are you recognized a lot more in New York, then say, Chicago right now?

DM: Yeah, I think it's mostly New York. That's where I do most stuff. I walk around a lot, I like to go for walks so... it's just increasing the changes. But I'm still pretty safely under the radar.

WW: I'm always curious about how people got started in stand-up. I know you dropped out of law school [at NYU law where he was attending on a full-ride scholarship] and plunged into the comedy world. When you first did that, was that your sole means of support or were you picking up other jobs?

DM: Oh no, it was all temping. It was temping at first and then proof-reading. I was a temp proof-reader and then I got hired as the staff proof-reader for some online advertising stuff.

WW: So you were doing that and doing comedy as much as you could?

DM: I would just have the day job for forty-fifty hours a week, whatever, and then standup at night. And I was writing jokes all the time, thinking about jokes all the time.

WW: Do you remember the first time you ever performed?

DM: Yeah. It was Bastille Day '97. July 14, '97. I got laughs. I gave like twelve jokes and got laughs on six of them. My goal was to get one real laugh and I got six; I was thrilled. I'm sure if I could find the cassette - I taped the set, but I lost it - I would be like wow, this is all terrible. But at the time I couldn't believe that I got any laughs.

WW: How long do you think it took before you started finding your voice and thinking wait a minute, I might be pretty good at this?

DM: I honestly feel that I'm still trying to figure that out. I'm glad that I have more material now, and I know what I think is funny. But when I first started I would meet comics who had been doing it a lot longer than I had at that point and I would ask them the exact questions you're asking and they would say, they would be like seven years in and they would say, "Yeah, I think I'm just getting it now." And I would be like, "Really? Can't you say a month or two?" But those first few years kind of fly by and I definitely feel in the last two or three years... doing my first one man show around 2002, 2003, that was very helpful in finding how to be, I guess, more authentic on stage. I just started feeling more myself. It wasn't just one-liners. People know that I do one-liners, which I love doing and I love writing. But there are a lot of other things that I like to do and I'm slowly finding ways to do those things.

WW: With the artwork and the music and more the concept of an actual one-man show, as opposed to just stand-up?

DM: Yeah. And the thing is with a one-man show, it's hard to do those in comedy clubs...

WW: That was my next question: Was it harder to get gigs starting out because of the type of material that you did, the more cerebral nature of it?

DM: I was told by the Gotham Comedy Club in New York... I don't like that place. They wouldn't book me because I was too low-energy and cerebral and not the traditional stand-up that they wanted their audience to watch. In fact, I was even booked on a benefit show there, so it was kind of somebody outside booking it, and the booker called me to take me off the show.

WW: So did you have to navigate clubs off the beaten path in NYC?

DM: I got up at the Comic Strip, I got up at the Cellar, I got up at the Boston Comedy Club, which is now the Comedy Village, so I found ways to get stage time. But they were kind of not frequent spots and some of the places, were, well, let's just say I'm not a big fan of a lot of the clubs.

WW: That brings up my next question about this "indie comic/comedy" label that I'm sure you can't avoid in every interview you have these days. But is that kind of the career you have strived for, one outside the mainstream comedy clubs, in atypical venues?

DM: Maybe. It's a pretty simple thing in the beginning, which is just you're just trying to get up in front of people to make them laugh. You just need that audience. It's a laboratory that requires other people, so wherever you land, wherever you're actually getting spots, you just keep going back there. It's pretty natural, it's a very natural sorting that happens. That's really how everything emerged, and then eventually in a lot of the rooms I found people who liked what I was doing, and I started to find big crowds. The thing I'm most grateful for on this tour is that I'm playing for crowds who want to be there and know what they're getting into. It's great, it's so different than when I was doing spots in the laundromat that I did on 7th Avenue, or the Krispy Kreme that used to be on 8th Street, or the bottom of B3 up on Avenue B, which, all those places could be good on any given night, but it was just really different. Those shows were useful for sure, because you learn other skills in there.

WW: How did the Conan and Daily Show gigs come about?

DM: The Conan gig came about because that was my third submission of a writing packet. So they knew me. I did stand up on his show for the first time in 2000, I got hired in 2003. That was over a few years, one time they picked me and I got the job. The Daily Show, they just knew me as a comic around the city and they were looking for new people on the show, so they called me in and they said they want to do stuff with me so I said great. They said pitch us some ideas and I gave them one and they were like, let's do that.

WW: It seems like you get to play yourself there.

DM: That's why it was cool. They said from the get-go, we want you to do what you do and we'll see if it fits into the voice of the show. I kept thinking, I don't look like a reporter. What I have to offer is pretty specific, but I guess it made things harder but kind of better.

WW: I saw you in Aspen a few years ago. Have you ever been out to Colorado besides that?

DM: I went to Aspen twice and I went to the Air Force Academy Summer Science Seminar when I was in high school; I got to go to the Air Force Academy for a week. It was pretty fun. They tried to get nerds like me who were good at science, I guess, to join the Air Force, so you go there for a week and it's all paid for and you take these little fake classes. And then the Air Force called me for another five years after that to get me to join. I skied out there once. But other than Aspen, I've never been able to perform in Colorado.

WW: I was really impressed with Leo Allen, Eugene Mirman and Michael Showalter, who came out here a little bit earlier on a tour together. I was talking with them after the show and it seemed pretty cool to me that these are guys who are well-known but not mega-stars yet known enough that they can put together this tour and get in a van together and drive all around the west and northwest, like they are a small band or something. Do you think that's the future of stand-up right now?

DM: Yeah, it seems like that's the future of a lot of live performance. It's all this internet stuff. People can find an audience and people can be very specific about what they go see if they have the energy to do some research and find out what's out there that matches their tastes. It's great. Especially if your needs are not too great. If your needs are to be some superstar, well, then that takes what it takes, I guess. You have to really hustle. But if you just want to do shows for good crowds that don't have to be huge, you can do it. I mean, making money is still pretty tricky. You can do those shows, but the money thing is another beast. I know a lot of us comedy nerds — nerd comics, whoever we are, Eugene, Leo, whoever we are, my friends - the fact that we can go to a place like Michigan or Colorado and know that there are people there that are going to like and get what we do is very encouraging.

WW: When you think about the upcoming year for you? What in your career gets you most excited right now? What are you most looking forward to?

DM: That's a good question, because I always think of things in those terms; I always try to think of what am I excited about doing, what am I looking forward to. I usually think of it on day-to-day things, which helps me break down and incrementalize the things I'm getting into. Because you have a better chance of quality of life there, as opposed to man, I'm going to make this big movie. I don't know, I'm kind of torn. I really want to learn how to play the drums. The thing I want to do the most is the thing there is nothing to do with. Those screenplays [he currently has three in the works, one green-lit by Steven Spielberg] I'm excited about, because those are real opportunities. But there is a part of me that just wants to draw. I'm reading a lot of art books lately.

WW: What kind of artists are you into these days?

DM: There's a guy name Tom Friedman I love. He just does kind of like sculpture, he just makes a lot of cool, weird different things that are really simple and they're usually made out of very accessible objects like an aspirin or toothpicks. It's really cool.

WW: When is the show in Austin? When are you recording?

DM: November 18th. So Boulder is my last show before that. Besides some weird pre-tape stuff that will just be in the special, the show on the 16th will pretty much be the one man show that I'm recording.

WW: I know it's a one-man show, but I love on your album how you have your friends come up. Are you going to play around like that a little bit?

DM: I'm hoping to, yeah. I'm trying to work out those bits, but I have to figure those out on the road as I go. I've been tweaking some ideas. I also want to get better at music because I want to put some live music in the show, more than I did in my first one, and I'm, like, not quite good enough.

WW: Are your mom and your grandma going to come out for the filming?

DM: I thought they were and I had some bits in mind where I was going to use them and I just found out that they are going to Vegas on a vacation with some other people from church and they're ditching me. They're choosing to go to Vegas over my special. My probably only one hour special ever. So I might cast actresses as my mom and grandmother to get back at them. But I'll make sure to say that these are not my actual mom and grandmother.