Jon Stewart and The Daily Show is to Comedy Central what Ted Koppel and Nightline is to ABC: the voice of reason in a world gone off its rocker. In Stewart's ever-growing corner of the cable universe, nothing—from the Terri Schiavo controversy to the war in Iraq—is sacred, which, thanks to his barbed-wire wit and benevolent brain, leaves 1.2 million viewers going to sleep feeling amused, challenged, understood, and a little less alone every Monday through Thursday night. As for those nights he's not on the air, I suggest you survive them by reading his very funny 2004 best-seller, America (The Book)—you'll laugh, you'll cringe.
I laugh the minute Jon Stewart opens the front door to his lower Manhattan townhouse (he assures me it's not normally filled with many bouquets of fresh flowers) and introduces me to his 9-month-old "man-wich," Nathan, who burrows into the crook of his arm, as his wife of five years, Tracey, comes to join us from the other room. It's a lazy Sunday morning, the perfect time to curl up on an overstuffed sofa and reflect on how Jonathan Stuart Leibowitz, the product of divorce, the class clown, the nice Jewish boy from Lawrence, New Jersey, went from kid with a college degree in psychology to brilliant stand-up comic to serious contender in the battle for talk-show-host supremacy. Contemplative, grounded, and awfully cute, Jon Stewart settles his son in for a nap and sits down for a chat.
Oprah: I've heard a lot of comedians say their humor is born of pain. Do you believe that?
Jon: If you looked at anybody's life, you could find the pain in it and say that what they do is born of that pain. Everybody's got their shit. I come from a straight-up middle-class existence. It was the seventies—"I'm OK, you're OK"—and we got hit with all of that.
Oprah: How did that affect you?
Jon: Man, I wish I knew. I'm sure I'll find out ten years from now. Someone will spill the gravy, and I'll flip out and start yelling. Anyway, what I'm trying to say is this: I don't think what I went through is any more remarkable than what anybody else goes through. My way of handling it was with humor.
Oprah: I read that you were teased as a child.
Jon: Who wasn't?
Oprah: But weren't you teased about your last name?
Jon: Yes. There's a lot that rhymes with the "itz" in Leibowitz. But if it hadn't been that, it would've been something else.
Oprah: I was called Okra.
Jon: Did you tell them, "I'm going to have an Angel Network"? Did you say, "I'm going to have a Wildest Dreams bus one day, and you're going to need a house—and I'm not gonna flippin' give it to you"?
Oprah: No, my big thing was that I never heard my name called on Romper Room. So you said earlier that you were fired a lot. Wasn't it hard to keep your self-esteem?
Jon: That wasn't a problem, because I didn't have any. I was good at what I cared about—like playing sports and drinking—but unfortunately, there wasn't a big market for those things.
Oprah: In 1993 you were a finalist to replace Letterman on NBC. Weren't you disappointed when you didn't get it?
Jon: Oh, yes. The Letterman job was big. But, you know, this is a business of rejection. I remember my first night onstage was at the Bitter End at 1 in the morning on a Monday. I was heckled almost immediately. On your first day of work at McDonald's, there's at least someone behind you who knows how to work the register. At some point, you can say, "Could you come over here, please? This guy just ordered a McFlurry, and I don't know what the hell that is." In stand-up, there's just you. You have no idea whether what you say will work. I was always funny in a back-of-the-room way. I can make my friends laugh. But the people at the Bitter End weren't my friends. They were drunk—and they thought I was going to be good.
Oprah: Is it harder to perform when the audience is drunk?
Jon: Easier. Inhibitions are gone. These days when people come to see me, it's more of a theater experience. They've paid their money, they're sitting down....
Oprah: And their expectations are higher.
Jon: Yes, but their willingness to believe I'm funny is also greater. It's like, "I've paid $60 to see this man, so clearly, he must be good. Otherwise, why would I have paid such ridiculous money?"
Comedy is the only form of entertainment where the audience doesn't know what to expect. In an evening, you might get ten comics doing ten different things. That's not what happens when you go to hear music. There isn't a classical performance followed by a hoedown followed by rap.