Jon: There are a lot of people saying what we're saying, but I hope we're doing it in a funny and artful way.
Oprah: You are.
Jon: I'll take that. It's not about power. It's about allowing more people to sample knowledge because it's baked in a delicious chocolate cake.
Oprah: And you don't have an agenda?
Jon: We do have an agenda—just not the one many people think we have.
Oprah: Do you have an intention?
Jon: Ooh, well done! Yes, and it's a selfish one. The barometer I use is mostly internal. A bad day for me is when I feel incompetent, not when I feel powerless.
Oprah: What makes you feel incompetent?
Jon: Poor execution. The show is a recipe of the silly, the relevant, the didactic, and the bawdy. We try to mix it in just the right measure so that it tastes delicious but still has enough nutrients. I would love for this show to be as competent as Seinfeld. I just want to be really good at what I do and feel good about doing it.
Oprah: Do you?
Jon: On more days than I deserve. But some nights, I'll come home to Tracey and go, "Honey, I got no mojo." It takes a while to hustle your way out of that—especially after a kid.
Oprah: Has parenting surprised you?
Jon: There's always talk about the red-blue cultural divide. But I'm surprised at the difference between having kids and not having any. Tracey says she now sees everyone as somebody's kid. When I look at Nathan, I think, I could kill someone for him. In fact, I could do it almost every day. When I see people walking down the street, it's like, Somebody is crazy about this person in a way that hurts his heart.
Oprah: Or somebody needed to love that person.
Tracey: Now we sometimes see people and think, Somebody wasn't so good to them.
Oprah: Since you've hit your stride on The Daily Show, do you feel successful?
Jon: I feel comfortable in my own skin. For me, that was the battle.
Oprah: When did you win it?
Jon: What time is it? When you walked in the door and I didn't cry. No, really—it was gradual. After college, I bartended while working for the state on a puppet show about disabilities—I was literally helping and hurting people, all on the same day. While the show was a noble effort, it was completely unsatisfying for me because I didn't feel part of it. When I dreamed, I dreamed of being somebody else. I realized I needed to create something I felt part of. Then slowly, that feeling of wanting to be someone else went away.
Oprah: You'd rather be yourself.
Jon: Right. I think that's a huge victory.
Oprah: I think so, too. If I come back in a second life, I want to come back as me.
Jon: [Laughs.] You know what? I'd like that, too.
Oprah: In the early nineties, I realized I'd been imitating others because I thought I needed to. I now know that the show has to come out of me.
Jon: Otherwise, how could you sustain it? When I first got on Letterman five years into my career, I thought, This is it—the end of my rainbow. He was the Carson of my generation. On the show, I did as well as I could. When I woke up the next morning, I wasn't any taller, I had a head cold, my apartment still had roaches. That's when I realized, This isn't about moments; this isn't about getting to the next place. It's just about being good. Then I got a show on MTV.
Oprah: What was that called?
Jon: Such an original title—The Jon Stewart Show. That did well enough for me to get Arsenio Hall's job after he quit. I was scared shitless. About four months into it, I thought, "Wow, this unbelievable opportunity will be taken away from me, and when someone asks, 'Did you even enjoy it?' I'm going to say no." I remember the night when I just exhaled.
Oprah: That happened to me when I was onstage dancing with Tina Turner. The song was only three minutes and 27 seconds long, and I was so nervous. Suddenly, a voice in my head said, "You've already wasted a minute. You'd better enjoy this!"
Jon: If this were Hollywood, the story would be that I relaxed and then built an empire, and 30 years later, that show is still going strong. Well, I relaxed, and five minutes later they locked my door and didn't let me back in the building. I got fired. But I had a hell of a time. I woke up the next day and it was the opposite of the Letterman experience. I thought, "Okay, my apartment is no worse and I can still write jokes." In that moment, I realized I had suddenly become competent. I had lived through the loss I feared.
Oprah: That's a pivotal adult moment.
Jon: A month later I met Tracey.
Oprah: How did you meet?
Jon: On the only blind date either of us had ever been on, at a Mexican restaurant.
Tracey: The date wasn't blind for me.
Jon: Tracey had seen me on TV.
Tracey: It's a fairy tale from my end. I had just gotten out of a seven-year relationship. I was depressed, and my friends were trying to set me up all the time. After a bad date, they'd ask, "What are you looking for?" I had discovered The Jon Stewart Show, so I said, "Someone funny and sweet, like Jon Stewart." My roommate was working on a movie set, and Jon knew someone who worked on that set. So Jon stopped by to say hello. They were all sitting around talking about how they weren't having much success with dating. My friend said, "I have a roommate who thinks you're cute. She saw you on TV." And, of course, Jon immediately thought...
Tracey: Right. Because my roommate was always setting me up with actors, I'd said, "No more performers." So she told Jon, "Actually, it goes against you that you have a television show." Then she told him more about me. Jon said later that he'd never heard someone talk in such a loving way about a friend.
Oprah: So was there chemistry at the Mexican restaurant?
Jon: I thought she hated me.
Tracey: I was embarrassed by how we met, and so nervous that I couldn't eat.
Jon: The date was literally me talking and eating. I cleaned my plate and part of hers. Then after I got a couple of drinks in her...
Tracey: I wouldn't stop talking.
Jon: So now I just keep her drunk.
Oprah: How long have you been married?
Jon: Since May 2000. But we've been together for ten years.
Oprah: Did marriage change you?
Jon: Tracey would probably say it didn't change me fast enough.
Tracey: I think it changed your living environment.
Jon: Let me put it this way: If I were single, this interview would have been a much different experience. You'd be surrounded by boxes.