I first heard Steven Wright’s I Have a Pony when I was in high school. It was a little more than 10 years after the classic comedy album’s 1985 release, but it was as if the jokes existed in this bizarre vacuum of hilarity—you could drop Wright’s dispassionately delivered one-liners into a time capsule, bury it for a thousand years, dig it up, and people would still laugh at them.

Paste: It’s been over two decades now since I Have a Pony firstOn June 2, Warner Bros. reissued I Have a Pony in a deluxe CD/DVD anniversary edition. Paste recently caught up with the comedy legend, who currently sits at #23 on Comedy Central’s list of the 100 Greatest Standups of All Time, nestled right between Robert Klein and Redd Foxx.

Paste: It’s been over two decades now since I Have a Pony first came out. I was wondering if over the years you’ve ever figured out what exactly you’re supposed to add to powdered water?Steven Wright: [laughs] No, I never figured it out.

Paste: When I interviewed George Carlin a couple years ago, we talked a lot about how, on stage, he used exaggerated anger as a device. You’re really infamous as this master of deadpan, but I’ve always been curious, how does the real Steven Wright differ from the character that you’re doing in your act?Wright: My act is an exaggeration of a part of me. I’m much more expressive off stage. But you know, you can hear by my voice right now—it’s the same. I was always just concentrating so hard on doing the material that I had a straight face, ’cause I was taking the thing seriously, so that became my style. So I guess I’m a little bit more expressive in real life.

Paste: Who were some of your favorite comedians, who were people who inspired and influenced you, and what was it about them that inspired you?Wright: Definitely Carlin was one of them. One of the reasons I wanted to be a comedian—I liked how he talked about all the little everyday things in life that people don’t usually talk about. And Woody Allen had a double comedy album. I listened to a radio show in Boston when I was a kid—every Sunday night they played two comedy albums. That’s where I heard Woody Allen’s album. And I liked him the best, the way he structured jokes and just the way he told stories. So those two guys definitely influenced me.

Paste: When did you decide that you wanted to be a comedian, and when did you start working toward that? Was it when you were younger, or in college?Wright: It was about when I was 14 or 15, and I thought that that’s what I would like to do, but I didn’t do it until after I got out of college. There was a [new] comedy club that opened up in Boston, and I thought, “Well, I gotta go down and try to do this ’cause it’s been in my mind for nine years. I was 23. So I wanted to try it and have it either work or not work, but at least I wanted to try doing it.

Paste: What was that first try like? How did it go? What are your memories of that?Wright: Well, I had written about three minutes of material. I went to see a show, just to see the comedians, and they were really funny. Then two weeks later I decided to go back for the open-mic night. And I was really, really nervous, ’cause I didn’t want to really talk in front of a group of people. But I wanted to do the stand-up so I forced myself to do it. It was very nerve-wracking. And they laughed at about half of it, which was pretty good actually, but I was disappointed ’cause I thought they should have laughed at all of it, but that was just ’cause I was so naive. And I kept going back to the open-mic night ’til they put me on regular nights.

Paste: Your voice is something that people love so much about you, and it’s such a huge part of what you do, but when you were younger, was it ever something you had to deal with—was it ever something that kids would mess with you about?Wright: No, never, ever. I never even thought of myself as deadpan until someone wrote an article about me about a year after I was doing comedy. There was a paper called the Boston Phoenix, and someone wrote a description of what I was doing and that’s where I first saw “deadpan.” But no, kids weren’t teasing me about it, no.

Paste: How do you feel about that description—deadpan?Wright: I remember thinking, “Wow, am I a deadpan?” I remember thinking that—’cause you know when you’re yourself, you’re just inside yourself; you’re not seeing yourself from the outside, and I remember stopping and thinking, “Wow, am I really deadpan? I guess I am. I guess so.” It was news to me.

Paste: Before you were actually doing comedy, what was it about being a comedian that appealed to you?Wright: It was something about, like, seeing the guys on Johnny Carson, seeing Johnny Carson come out and do the monologue, and then seeing the comedians he had on. It was just something I was drawn to—these guys, doing this alone thing, and making these people laugh. I just thought it was kind of a cool thing. I’m not even sure how to explain it really, I just thought—I saw Carlin and Robert Klein and David Brenner, and I thought, “Man, I wish I could be one of those guys.” But I’m not exactly sure why. I just thought it was an interesting thing to do.

Paste: Tell me about your early days that led up to your breakthrough performance on Carson. What was it like? Were you playing a lot of small comedy clubs, kind of working up your material?Wright: There was two clubs in Boston, the Comedy Connection and the Ding Ho Comedy Club in Cambridge, and I started doing regular nights. I would do maybe three or four shows a week, and then during the early ’80s, comedy was exploding—you could do a set at one club, then go to the next club and do a set, then go back to the first club and do another set. So I was doing lots of time on stage ’cause there was so much comedy around, and you learn it by doing it. I mean, I had no money at all. I remember taking the subway—I’d have to go around my apartment to get enough change to go on the subway to get to where the show was. And then they’d pay you under the table—first it was like eight bucks then it was like 20 bucks and it started going up from there. But I was doing that, at that level, for about three years before the TV happened.

Paste: Were you working other jobs at that point?Wright: No, I started in July of ’79, and I was painting the college that I went to, painting the rooms, and then I worked as a cashier in the MIT Coop, the store at MIT. And then when I was doing comedy about six months, I was making enough money to pay the rent—the rent was like a-hundred-and-fifty dollars a month—I quit working in the day, so then I was just doing comedy at night.

Paste: Your appearance on Carson—how important do you think that was to launching your career?Wright: Oh, absolutely, it was the catalyst of the whole thing. I mean I was playing little clubs in Boston, and Peter Lassally from The Tonight Show came to Boston to look at colleges for his kids—they were graduating soon. And he read an article about the Ding Ho Comedy Club, it was an article in the L.A. Times about it ’cause it was such a weird place—comedy and Chinese food—and so he went to see this comedy club to see the comedians, and two or three weeks later I was on The Tonight Show and my whole life changed, my career and my life changed from just that first appearance.

Paste: Was it difficult to get a handle on things because it happened so fast that you went from just kind of a local guy to like this big national comedian?Wright: Um, it went fast, but it wasn’t hard to handle actually. I mean, I went on The Tonight Show on a Friday night, and then the next Thursday I went on again, and then I came back to Massachusetts to continue working in the clubs, and then a couple of months later I moved to L.A. And then I was doing Letterman and Saturday Night Live. It was fast, but it wasn’t hard to handle.

Paste: What’s the writing process like for you—is it something where you sit down, you work at it, or is it as simple as walking down the street and having a strange thought or a funny thought?Wright: Yeah, it’s the second one, definitely. Just from hanging out, doing whatever I’m doing. From the minute everyone wakes up to when you go to sleep, there’s little fragments of information that you encounter on a daily basis, and some of it just jumps out as jokes to me.

Paste: Do they come pretty regularly, or is it just kind of sporadic?Wright: It, it comes sporadic now. They used to come lots, in like groups of them, but now it’s sporadic.

Paste: On June 2, Warner Bros. is putting out the deluxe anniversary reissue of I Have A Pony. Looking back after almost 25 years, how do you feel about that album, and the material, and what do you remember about that period in your life?Wright: Well, it came out in ’85, and I did an HBO special at the same time, and it moved me from clubs into theaters when those two things came out. I’m gonna go on Letterman on June 5, and I’m gonna do material from that album, so I was listening to it a few weeks ago to figure out which material to do, and I really liked it. I was surprised—I didn’t know how I thought of all those things. To tell you the truth, I was kind of like, “Man, where did I come up with that stuff?” It was so twisted and weird and interesting, and I was seeing it almost like a fan would see it, ’cause I hadn’t listened to the album in a long time. But it was definitely a good time in my life when that album came out, and I’m happy that it’s coming out again so that younger people who maybe never heard of it can get into it. Reach a whole other generation.

Paste: That album was nominated for a Grammy—did that matter much to you? Do you care much about things like that?Wright: Yeah, I feel really proud that it was nominated for a Grammy. I think that’s great—I still kind of can’t believe it. The Grammys were up at this level. You know, it’s just cool to think you can be nominated. I did another album that came out two years ago…

Paste:I Still Have A Pony?Wright: Yeah, that was nominated, too. And, yeah, I liked that they were both nominated.

Paste: If there’s ever been a criticism about your work, over the years, there have been some people who have complained about how long it takes you to write new material. When you hear stuff like that, how do you take that kind of criticism, and what do you think you would say to those people if you had a conversation about it?Wright: It does take so long, ’cause for every five jokes I only think of one or two that is good enough to stay in my act. But I don’t think about, I don’t think about the people complaining about that—I have enough things to worry about in my life. And, you know, the jokes are gonna come when they come, and I can’t help it; I can’t do anything about it. ’Cause I don’t even sit down to try to write the new—it would be too forced. So I just have to wait for it to happen.

Paste: It’s not like making sausage.Wright: Yeah, yeah. It’s not like an assembly line in my house.

Paste: [laughs] Actually, that’s an interesting idea. I’m trying to imagine the assembly line that would be in your house to make jokes.Wright: [laughs] Yeah, that’s funny.

Paste: So what have you been up to lately? I know you did the follow-up to I Have A Pony—I Still Have A Pony—two years ago. Have you been working on anything lately? Any new material or tours planned, or any film projects?Wright: I’ve just been doing live shows here and there, but I’ve cut back a little bit on them. I did a few a couple weeks ago in three cities, and now I’m gonna do another five or six cities, so since that album came out I’ve been on and off the road. I haven’t been working on another project; I’ve just been doing live stuff. I was out in California, I went on the Craig Ferguson show about six times in eight weeks, but I’m not working on a film or anything right now.

Paste: I’ve got one last question for you. You’re a big Red Sox fan—what do you think is up with Big Papi’s (David Ortiz’s) bat this season and what’s he gotta do to fix it?Wright: So discouraging. I feel bad for him ’cause he seems like a nice guy, and he must be tortured. I don’t know what to think of it—I’m kind of scared to think that maybe he’s not gonna come back. He has one home run, right? And I don’t know, I feel bad for him. You can see when he walks back to the dugout after he flies out or strikes out, you can see he’s disturbed by it. But, yeah, I hope he snaps out of it. I feel bad for him.

[Ed.—looks like Wright might be getting his wish. Since this interview, Ortiz is in the midst of a seven-game hitting streak. In fact, he hit a home run the night this story was published.]