Judd: What’s fun is that now you’ll probably end up talking to the president about it at some point, because it’s inevitable he will be a guest on your new show.
Stephen: I don’t know about that. Nothing’s inevitable. I would like it, though. I wrote him a letter afterwards saying I hope he enjoyed it, it was an honor. Maybe he burned it.
Judd: What is your sense of how Republicans and Democrats feel about your show?
Stephen: I mean, it has been hard to get Republican politicians to come on the show. But I saw this study once many years ago, from Ohio State University, the graduate program there. They did a study of self-identified conservatives and self-identified liberals, and they got a group that self-identified in those categories, and that also both sides identified as fans of the show, and they had them watch the same video, then they said, “What do you think his actual political position is here?” Democrats believed that I was a liberal or liberals believed I was a liberal pretending to be a conservative, and conservatives who enjoyed the show tended to think that I was a conservative pretending to be a liberal pretending to be a conservative.
Judd: (Laughs)
Stephen: And I don’t really want to correct either side, because there are times I agree with my character. And I really don’t want the audience to know when I do. I love that, man. That’s the triple gainer. I purposefully jumped over the line a lot at the beginning of the show so people would be confused.
Judd: Is it strange for you, as a comedy person and an improviser, to be tossed into the center of public political life, and to be surrounded by the players—
Stephen: That was the point of it. The whole point of it was to do that. Jon Stewart used to say when we were over there, “We’re the kids in the back of the class shooting spitballs, you know?”
Judd: Yeah.
Stephen: And I wanted to be the spitball. I remember when I ran for president for the first time in South Carolina, people—people who have known me for years and really understand me—would call me up and say, “Listen, you got to help me out here. I am trying to deal with people who are freaking out about this. Is this real or is this a joke?”
Judd: (Laughs)
Stephen: And that’s the first time I realized what I really liked about this. If it wasn’t real, it wouldn’t be a joke. Or it wouldn’t be a joke I’d want to do.
Judd: Yes.
Stephen: I wanted to do it to see what it was really like, because when I really ran, I really had to deal with federal election law. I really had lawyers up my ass. I really had to find out, like, Wait, I can actually be sponsored by Doritos? Okay, my candidacy can be sponsored by Doritos, but I can’t actually talk about Doritos when I talk about my candidacy? Or I can eat Doritos that I bought myself, but I can’t eat Doritos that Doritos gave me? Or, like, when I actually formed a super PAC, or sponsored the Olympics, or testified before Congress, or held a rally with Jon on the Mall, or…We always say here that we can make jokes about anything. Where do we point the gun?
Judd: Yeah.
Stephen: The hard part is deciding what’s worth shooting.
Judd: How much money did you raise?
Stephen: Over a million dollars. Significantly over.
Judd: Why do you think people gave you money?
Stephen: They wanted to play the game. We established this lovely relationship with our audience where—early on, we called them the Colbert Nation, okay? “I’ve got to watch where I point this thing, okay? You people are powerful, I’m your leader. We’re going to change things. We’re going to make the world a better place.” I said that on the first night, and I started calling them the Nation. Well, what we didn’t realize is our audience was accepting our initiation that they were a character in the show. And that super PAC was the ultimate game they played with us. We went and held rallies. We raised money. We ran commercials. We got in trouble. We said, “You give us the gun and we’ll go fuck shit up. We’ll start shooting it in ways that are both legal and unethical.”
Judd: (Laughs)
Stephen: And our audience enjoyed being in a little gang. That’s a fun thing. We all had a place. There was an intimacy that I would never want to lose again. I know that’s possible now, and I never want to lose it.
Judd: Were you thinking about winding down the show before the offer to do the talk show came in?
Stephen: Yes. As I said earlier, I was sick of the model. And I realized: If I want a change, I’ve got to leave.
Judd: What are your thoughts about switching to something that is just transparently your personality—and about, on some level, sincerity?
Stephen: We shall see, Judd Apatow. We shall see.
Judd: Were you a fanatical Letterman fan?
Stephen: Yeah, yeah. I mean, I am the ur-audience. His show started in ’82, the year I started college. Dave was it. Johnny was great, I loved Johnny. I’m the youngest of eleven children, and my elder sisters would wake me up to watch Carson with them because they didn’t want to watch it alone. I would be like a toddler watching Carson with them, but Dave—Dave was like us. Dave was stupid. And I loved it. His disrespect was to his own form.
Judd: I was completely obsessed with Letterman, too. When I was in college, I—this is a terrible story. I haven’t told it in a long time, but I sent a letter to every single staff member at Letterman asking for an internship, and someone called me, and I flew to New York, on my own dime, for the interview. When I got there, the woman told me there was no job, it had already been filled. I flew home and wrote her the meanest letter, using words that could end my career right now.
Stephen: Oh my God. You know, I was offered a Letterman internship.
Judd: And you didn’t take it?
Stephen: My girlfriend my senior year of college—she was coming out to New York and I came with her. She was interviewing for an internship at Letterman. I don’t know how she got it. I didn’t know internships existed. I didn’t know anything like that, didn’t know that was an option. I went with her to the interview. It was at 30 Rock, and she went in and she was having her interview and somebody opened the door next to that room and said, “Are you the next guy?” I said, “No, I’m just here with my friend who is in there talking.” He goes, “Well, do you want to come talk?” So I went in and we had a nice conversation, and then they called me and said, “You got the internship,” and she didn’t get it.
Judd: Did the breakup soon follow?
Stephen: We did not last the summer. But I turned the job down, because I was like, “What? You don’t pay? How can I go to New York and not—what? What do you mean I move to New York and you don’t pay me? What do I do, live in a trash barrel?”
Judd: See, I would have lived in the trash barrel.
Stephen: It would have been fun, but again, it wasn’t on my radar.
Judd: And when did you—just so I understand the trajectory a little bit, you were attempting serious theater at this point?
Stephen: Yeah, I was studying at Northwestern University’s theater program, and you know, I was doing Stanislavski and Meisner and I was sharing my pain with everyone around me—it was therapy as much as it was anything. I met a guy there who said, “Hey, have you ever seen comedy improv?” I said no. He said, “Well, I’m going down to see these guys in Chicago do something called The Harold. Do you want to go see it?” I said sure. So I went down to a place that doesn’t exist anymore called CrossCurrents, which was beneath the Belmont L in Chicago, right near Ann Sather’s. Best Swedish cinnamon rolls in the city.