Jon Stewart
For those of us who like our news with a side order of satire, Jon Stewart's The Daily Show is the best thing that's happened to cable. Now, the man who never met a politician he couldn't laugh at riffs on his early years, the boos he's bounced back from, the comedians he admires, the infamous Crossfire incident, and how a blind date changed his life.
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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.
Oprah: Comedy is a ride.

Jon: Some people respond to wordplay, others to props. Everybody thinks they're funny or knows somebody who's funny, so people don't view comedy as a talent. They view it as a cry for help.

Oprah: I beg to differ. There are many people who realize you have a talent they don't have.

Jon: Do you mind if I put you on the phone with my father right now so you could repeat that last sentence to him?

Oprah: Oh, absolutely. You say what everybody else is thinking but can't articulate, in a way that makes people laugh. That's a gift. Chris Rock also has it.

Jon: Chris is unbelievable. I'm very able to appreciate it in other people.

Oprah: So who impresses you as a comedian?

Jon: Chris. David Letterman, Garry Shandling, Adam Sandler.

Oprah: What's a typical workday like for you?

Jon: We usually work ahead—being a fake news program is a huge advantage. On a weekday morning, we might think of the most visceral aspect of the Iraqi elections—like "Now that we've had an election, we can leave." What's the best way to express that through stand-up? Someone might throw out an idea: Could we have the correspondent stand in front of a green screen that's moving? And on the reveal, you'd see he's doing his commentary while running the heck out of Iraq. But then we figure out, okay, we can't do that. It's all about having an ear for the right idea.

Oprah: Did you know that when you took over the show?

Jon: No. I just knew I wanted to do something different.

Oprah: But I've heard the staff wasn't with you on that?

Jon: That's correct. Tracey can attest. Many times she'd find me in the living room at 4 in the morning, smoking and having arguments with myself.

Oprah: How did you convince them to go your way?

Jon: I didn't. Those who were with me stayed; others left.

Oprah: Was it a conscious decision to move to politics?

Jon: It was a conscious decision to move to relevance—to make the show something people care about. I had done a talk show where it was, "Ladies and gentlemen, tonight we're doing three segments instead of two with Maria Conchita Alonso. Because it turns out the guy with the falcons is not going to come tonight." I thought, This can't be how I live my life. So I decided not to give a crap about what anybody else thought anymore. I did what I wanted to do, with like-minded people who'd bring passion, competence, and creativity to it.

Oprah: Did you feel that even when people started walking out?

Jon: I can't tell you how relieved I was when people started walking. I didn't have to fire them.

Oprah: I hate firing.

Jon: But anytime you can weed out crazy and bring in sane, it's worth it. A friend of mine used to say, "Why shouldn't a good person get the job? Why shouldn't competence be rewarded?" So I brought in Ben Karlin, a guy from The Onion [an online newspaper parody], and Stephen Colbert, and we developed a team that felt right. We got better at structuring the show. I always hear quarterbacks say the difference in the NFL now is the speed of the game. The difference in The Daily Show is the speed with which you have to digest material and turn it into a comedy-like pulp. When you look at Johnny Carson's old shows, you want to smoke a pipe, have a cup of tea, and relax. But our show moves. That's how TV is now.

Oprah: I've heard that the faster you tell a joke, the funnier it is. True?

Jon: I don't know, but I will definitely talk faster from now on.

Oprah: You really became part of the public's consciousness during "Indecision 2000." Do you deny that you are powerful?

Jon: Yes—I deny that I am powerful. Power implies an agenda that's being acted on.

Oprah: But more than anyone else, you have us thinking about politics differently.

Jon: Every generation has had its people who stand at the back and make fun of those in charge. When the Nazis came to power in the thirties, it created an incredible underground scene of satirical comedy. Peter Cook [a British comedian] once said with a straight face, "Yes, they really showed Hitler." That's how I see it. I'm not saying I'm powerless and in a vacuum. But if I really wanted to change things, I'd run for office. I haven't considered that, and I wouldn't—because this is what I do well. The more I move away from comedy, the less competent I become.

Oprah: I got that. People ask me all the time whether I'd run for office. What I do well is television. I wouldn't be effective sitting in an office trying to push legislation.

Jon: But if power were your aphrodisiac, you'd do it anyway. You could translate your influence into political power.

Oprah: I agree. I question your denial that you have a powerful effect on the way people think about politics.

Jon: Honestly, I'm not trying to be self-deprecating or even obtuse. What we're doing on the show is not original. If it weren't me, it would be somebody else. We set out to deconstruct the process [of politics] and give people a glimpse at what we think the reality is—and while we're doing that, we tell jokes. If I didn't do jokes, nobody would give a crap.

Oprah: When did the media become the be-all and end-all for influencing people's opinions?

Jon: When Gutenberg came up with that printing press. After that it was over. It's not about the media; it's that a means of communication will always be co-opted by people who want to use it for powerful purposes. And when we say "the media," do we mean me, Ted Koppel, or Rush Limbaugh? Those are very disparate voices. The media is really a bunch of feudal kingdoms that exist in a larger structure.

The Bush administration is actually doing something really smart: They're blurring the line between what's a voice of authority and what isn't. They've paid guys like Mike McManus and Armstrong Williams to go out and tout their programs and create news pieces. [Federal agencies allegedly paid several newspaper columnists to help promote the No Child Left Behind campaign and other initiatives.] These guys are government advocates working under the guise of "analysts." What's more confusing than that?

Oprah: Isn't that the ultimate in propaganda?

Jon: Yeah. The media started winning in 1960. That was the first time—when Nixon went up against Kennedy in the debate and said, "I don't need any makeup. I look freakin' great." Everybody watching went, "Oh my God. Who's Sweaty McSweatington?" They all voted for Kennedy. In the same way that Franklin D. Roosevelt recognized the power of radio, politicians now recognize the power of TV—and power doesn't want scrutiny. Noise is an advantage. I'm not even making sense anymore, am I?

Oprah: I get it.

Jon: I've got to ask, or else we'll be sitting around like, "Don't you get it, man? It's the media, dude."
Oprah: I think what your show has done, especially during the election, is allow people to ask, "Are we just being sold a bill of goods?"

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...

Oprah: Loser!

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.
Oprah: Where do you see your show going? I know that's tough to answer when you work on a daily program.

Jon: Right. After every show, we have a two-minute postmortem where we go, "Jesus, I can't believe we did that" or "We should have moved that piece up higher." And then it's "What are we doing tomorrow?" When I come home, Tracey says, "Who was on the show tonight?" and I have no idea because it's not about that. It's about hitting the next night.

Oprah: People come up to me and say, "I was on your show two years ago," and I have no idea who they are.

Jon: At least we only have one guest a night. The Daily Show is really about the writing. We've realized that people will become accustomed to our voice, and we have to evolve it in a way that's inspired. You can exist on television for a long time as mediocre. You can become comfort food. We don't want that. I can't imagine doing this 20 years from now.

Oprah: Are there topics you consider off-limits?

Jon: I hope our humanity saves us from producing nasty or mean-spirited shows.

Oprah: You caused a media storm by calling Crossfire host Tucker Carlson a dick when you went on his show last year. Do you regret that?

Jon: I regret losing my patience. That's about it. But calling him a dick? Not really. I was calling that guy who was on that show right there a dick—I don't pretend to know Tucker as a person. But I regret going on air as tired as I was and not being more articulate with what I wanted to say.

Oprah: That's what happens when you're on the edge.

Jon: I thought, Let's just end this on a sneeze!

Oprah: A-choo!

Jon: The TV networks have an opportunity to bring noise or clarity. So much of what the government and corporations do is bring noise because they don't welcome scrutiny. They don't necessarily want you to know what they're up to. So if you're working in a medium that has an opportunity to bring clarity and you instead choose to create more distraction, that's theater—which is what these news channels have become.

Oprah: Theater that isn't really challenging.

Jon: The reason everyone on Crossfire freaked out is that I didn't play the role I was supposed to play. I was expected to do some funny jokes, then go have a beer with everyone. By stepping outside of my role, I stunned them. Imagine going on Crossfire and expressing an opinion that causes a problem. Apparently, the only people you cannot put in the crossfire are the hosts of Crossfire. What they do isn't real. It's talking point, talking point, talking point. It's like, "We all understand this is a game. Now let's go have dinner." But for those of us watching at home, it's not a game. It's frustrating. And it wasn't their dismissiveness that riled me; it was their condescension. It was like, "How dare you come on here and not do what you're supposed to do?"

Oprah: Because you're supposed to be a comedian.

Jon: Right. What I ultimately said was, "Tomorrow I'll go back to being funny, and you guys will still blow." I have no respect for them. It was as if they thought I was suddenly taking myself too seriously. What do you think The Daily Show is about? Just because we're comedic doesn't mean we don't care about this stuff. We do.

Oprah: I love that you told John Edwards he'd have to announce his candidacy someplace else because it didn't count on a fake news show.

Jon: Right. My interview with John Kerry wasn't very good.

Oprah: You don't think so?

Jon: No. Our interviews either have to be really funny or find some humanity in the subject. I didn't do either. He remained guarded throughout, so it struck me as a boring fencing match.

Oprah: When I'm talking with politicians, I can't break that wall.

Jon: Politicians are salespeople. If you're trying to sell a product, what's more powerful than an appearance on Oprah's show? In the last four months, one book overtook America on Amazon. It's called He's Just Not That into You. When I saw that title, I said, "What the hell is that?" Somebody told me, "The author was on Oprah." So politicians see your show as their chance to display their theatrical humanity, not their real humanity. They come on my show to display their theatrical sense of humor—and to show that they're down with the kids.

Oprah: Kerry didn't accomplish that.

Jon: No, he didn't. Because he was—like I was on Crossfire—tired and in a certain mood.

Oprah: Right. So you don't think you'll be doing The Daily Show in 20 years?

Jon: I don't want to be. I love my wife, and we want more kids. I'm not going to disappear, but I don't want to work this hard.

Oprah: What kind of daddy do you want to be?

Jon: The kind who stays. The kind who doesn't say to a 9-year-old kid, "This doesn't mean your mother and I don't love you" as he's heading out the door.

Oprah: What's important to you?

Jon: That. I've achieved far more than I ever thought I would. I'm not complacent, but I don't think long-term. I tell myself, "If I get good at this, it'll be fun to do."

Oprah: Can you taste your success?

Tracey: I can taste it.

Jon: For her, it actually tastes like an online catalog. I just don't think it's in my nature to savor things. But I no longer live with a gnarly void, like an angry troll under a bridge.

Oprah: Isn't that what defines a real man?

Jon: That seems genderless to me.

Oprah: It's also what makes a real woman.

Jon: Yes. What I'm proudest of is moving to New York.

Oprah: You left the puppets.

Jon: Yes—and I surprised the crap out of everyone. I might have become a bitter guy at the end of the bar, complaining about how I could've been somebody. But I sold my car and moved up to New York with no job because I wanted something different. I yearned, and I went for it.


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