Jon Stewart: The Playboy Interview (50 Years of the Playboy Interview)

BOOK: Jon Stewart: The Playboy Interview (50 Years of the Playboy Interview)


About the Book

Copyright © 2012 Playboy Enterprises, Inc.

All rights reserved, including the right to reproduce this interview or portions thereof in any form whatsoever. For the full
archive—including every Playboy Interview ever published—visit

About the Series:
In mid-1962,
founder Hugh Hefner was given a partial transcript of an interview with Miles Davis. It covered jazz, of course, but it also included Davis’s ruminations on race, politics and culture. Fascinated, Hef sent the writer—future Pulitzer-Prize-winning author Alex Haley, an unknown at the time—back to glean even more opinion and insight from Davis. The resulting exchange, published in the September 1962 issue, became the first official Playboy Interview and kicked off a remarkable run of public inquisition that continues today—and that has featured just about every cultural titan of the last half century.

To celebrate the Interview’s 50th anniversary, the editors of
have culled 50 of its most (in)famous Interviews and will publish them over the course of 50 weekdays (from September 4, 2012 to November 12, 2012) via Amazon’s Kindle Direct platform. Here is the interview with
The Daily Show
host Jon Stewart from the March 2000 issue.

Jon Stewart, March 2000

Every evening, after the audience is locked and loaded but before taping begins, Jon Stewart bounds onto the set of
The Daily Show
to meet the people. He faces two sets of bleacher seats, cracks a few wry asides and takes questions from the crowd. Tonight a college student wants to know if Stewart will say the letters NYU on the show. Stewart mocks amazement.

“Why? If I do it for you I’ll have to do it for everyone.”

“Because I...I made a bet,” the kid stammers.

Stewart is suddenly interested. “Oh? What’s the bet?”

“I bet ten dollars. If you say it I win.”

Stewart mulls this over. “Will you give me half?” he asks. The kid seems hesitant, so Stewart adds, “Come on. I can’t feed a family on cable money.”

You can on the kind of cable money Stewart’s making: an estimated $1.5 million a year for four years as the new front man of
The Daily Show
with Jon Stewart
, Comedy Central’s designated successor to
Politically Incorrect
. And according to the critics and fans, Stewart (who also helps write and guide the show) is worth every penny. Maybe that’s why, late last year, in a New York Observer column “memo to David Letterman” lamenting
The Late Show
’s decline, Ron Rosenbaum wrote: “It started to go bad the moment your show stopped being about ridiculing big-ass, pompous television and started becoming big-ass, pompous television” and included an unexpected yet creative exit strategy: “Get Jon Stewart to replace you.”

Not that Stewart is angling to move on. He has the greatest respect for Letterman, whose show helped launch Stewart’s career, positioning him to have a talk show on MTV and, later, in syndication. And then there was the deal with Letterman’s production company to host either a 1:30 A.M. talk show or to replace veteran Tom Snyder, for whom Stewart served as guest host, on
The Late Late Show With Tom Snyder

Are you keeping this all straight?

Stewart is a bright talent whose lightning-fast prowess with the ad-lib and wisecrack is savant-like. Since taking over
The Daily Show
from Craig Kilborn, he’s seen the show’s ratings improve (while Kilborn, who took over the Snyder show, seems badly miscast in his new role). Critics have raved about Stewart’s self-effacing charm and smartass sensibility. That sensibility has been the secret to Stewart’s success dating back to his days as talk show host on MTV. He doesn’t try to be hip in the slightest, and yet he comes across as the hippest comic on television. It’s no wonder that one critic called
The Daily Show
“the smartest thing on the air.”

Jonathan Stewart Liebowitz, 37, grew up in the Trenton, New Jersey suburb of Lawrenceville, where he lived with his father, Donald, a physicist for RCA, and his mother, Marian, an educational consultant. The couple divorced in 1971, but otherwise Stewart’s wonder years were typical for a young Jewish boy. He wondered: Would he “grow taller, get better looking, get laid”? Meanwhile, Stewart took refuge in
The National Lampoon
and the defensive use of comedy to short-circuit any comments about his height, looks or religion.

At the College of William and Mary he got the answers to his questions (yes, yes and yes) and graduated with a B.S. in psychology, which he promptly put to use working as a bartender. His best drink: “A Whack in the Head—a mixture of Alabama Slammer and Long Island Iced Tea. Drink two and you’re not getting up the stairs.”

Stewart also worked for the state of New Jersey in various civic capacities and eased into a comfortable middle-class lifestyle that left him uncomfortable.

In 1987 he decided to pack his bag for New York City and test his secret ambition to do stand-up. His coming-of-age at the famed Bitter End was less than auspicious, but it still made him feel “better than anything else” he’d done. Even when another club owner told him that there were already too many Jewish comedians, Stewart didn’t retreat to suburbia. He got a job hosting
Short Attention Span Theater
on Comedy Central in 1991. In 1993 he tried out with every other comedian to succeed
Letterman on Late Night
; Conan O’Brien got the job. Eventually, Stewart appeared on an HBO
Young Comedians Special
, then did the
Late Show With David Letterman
. That shot got MTV interested and he signed on to host the half-hour
Jon Stewart Show
, which debuted in September 1993. Paramount expanded the format to an hour and syndicated the show. Soon it was being replaced by
reruns, shifted to the 3:30 A.M. slot and was canceled in June 1995.

During the next few years Stewart turned up in unexpected places, including
The Larry Sanders Show
, where he often appeared as himself and was a creative consultant. He also launched a movie career (
Half Baked, Playing by Heart, The Faculty, Big Daddy
), hatched a production deal with Miramax Films and wrote a humor book titled
Naked Pictures of Famous People
. Rather than rely on the stand-up material he’d already mined in his 1996 HBO Comedy special,
Jon Stewart: Unleavened
, Stewart wrote essays skewering the conceits of popular culture. It was an immediate
New York Times

In January 1999, Stewart replaced the host of
The Daily Show
and hasn’t looked back. “I’m very happy now,” he says. Even if it doesn’t get any better than
The Daily Show
? Yes, Stewart insists. “Let’s just say that if it never gets any worse than this, then I’ve had one of the luckiest runs ever.”

We asked Contributing Editor
David Rensin
, who last interviewed David Spade for us, to spend a few days with Stewart on the set of
The Daily Show
. Rensin reports:

“His office is littered with the detritus of celebrity: unopened champagne bottles, promo items, gift baskets and a biohazard container left by ‘a guy who did flu shots. I wanted something to remember him by.’ Jon’s mind is similarly littered, but with the raw material of comedy-to-order. He could send up any topic instantly, especially when he detected an intentional (or unintentional) set-up in my questions.

“For our second meeting, he asked if we could talk during the sixth New York Mets—Atlanta Braves playoff game. We ordered in pizza and Cokes. ‘This is going to be the best 12-year-old’s pizza party you’ve ever had in your life,’ Jon said. It was touch-and-go the whole game, and we would have watched the entire thing, but Jon kept calling his girlfriend to rave every time the Mets scored. Eventually he decided to catch the last few innings with her, and we said goodnight.

“The Mets lost, so I wanted to begin our next conversation on a cheery note.”


Thanks. [
] For what?

The Daily Show
the longest you’ve ever held a job?

That’s true. I started January 11, 1999. How did you know?

This is
We know everything.

We’ll see.

Tell us about the time you destroyed thousands of dollars’ worth of aquariums in what can loosely be described as a gymnastics accident.

know. [
] First, the tanks were empty. No fish were harmed in that senseless tragedy. It was 1976 or 1977. My brother was an assistant manager at one of the first mega Woolworths. He was a bit of a taskmaster, but good people. The main floor was filled with entertaining and wonderful items. I worked downstairs in the catacombs, with the stock shelves. To alleviate some of the boredom, we used to dive off the shelves. They were pretty high, but it was OK because this was back in the day of the beanbag chair. We’d pile them up and do whatever gymnastics routine we could imagine. Unfortunately, I hit a bag wrong and it shot across the room and wiped out thousands of dollars’ worth of aquariums. Fortunately, I had the key to the incinerator. But, much to my chagrin, aquariums make a lot of noise when they burn. It drew the attention of some higher-ups and my brother had to fire me.

Too bad. You probably would have made manager by now.

A major disappointment. But I sought professional help, improved my diving technique and haven’t hit the bag wrong in years. I know it’s one reason I’ve lasted so long with
The Daily Show

The Daily Show
to someone who’s never seen it.

It’s a pulsating hour of drama. Actually, if someone’s never seen it, chances are I won’t be talking to them; I force people to watch a highlight reel before each and every introduction.

And then you walk into the room?

Exactly. Then I say: “Do you watch the news? Do you think it’s funny? We do, too.” That’s pretty much it.

What specifically is funny to you about the news?

Not the news itself but how the news is delivered. The process of news. The parody is our bombastic graphics and the news song, the correspondents and their interaction with me. And by using the general structure of a news show, which we find inherently satirical, we’ve found a cheap way to get in 20 monolog-type jokes. Does that make any sense? [
] Judges? Too bad: The East German says no.

Perhaps an example would help.

Last night we had a bumper graphic that parodied how news programs tease viewers into watching the whole show: “10:11: Hero dog saves family. 10:13: Rapist on loose. 10:15: Do you know what’s in ice cream? It could kill you. 10:17: Sports.” Or look at the pomposity of
: the grandiose set, the guy sitting in his chair, then getting up and the camera moving in that slow, sweeping way, as the host asks, “Would he escape from the ocean after eight days of drinking his own urine? When we return, the answer.” Some news magazines will report on a murder trial while a ticker at the bottom of the screen counts people’s phone-in votes for which side they think is right. “When we come back, the defense will present some evidence you won’t believe!” It’s gotten ridiculous. So we make fun of it.

The Daily Show
your interviews are only four minutes long. How do you prepare?

Is it that clear that I don’t? It’s pretty standard stuff. Hank books the guests, does a preinterview, then comes in with a dossier and we put up their picture. We do this in a secret basement room. We talk about their physical characteristics, their emotional characteristics. Has there been a breakdown? Drug allergies? Any notes from a doctor. Mental pressure points. Did you ever see Slim Goodbody? He wears a suit with the human organs on the outside for all to see. We usually go over that for each potential guest to see if we can find any weak areas. Once we come up with a game plan, Hank sends it out by code. I can’t tell you much more because I’m already telling secrets.

In other words, you don’t prepare at all.

Hey, wait a minute! My goal is to be relatively spontaneous. The interview is really just a little something extra to throw into the show. It doesn’t even have an angle, like when Kilborn did Five Questions. We just want it to be light and entertaining. We want to put our guests at ease. The key is to get them to go far enough to give the appearance of a heightened conversation that’s not purely on the seller-buyer level. It’s an easy gig. If it ran five minutes, I’d be concerned.

Have you ever taken on a guest over a disagreement with him?

Not that I can recall, though that would be interesting. I’ve seen Chris Rock eviscerate people with common sense and wit while they sit there looking flummoxed. His interview with Representative J.C. Watts was one of the best I’ve seen. The Johnnie Cochran thing, too. We’d like to branch out into the political arena, but it’s really hard to get anybody with a stake in politics to come on a network called Comedy Central. It’s a fear of disgrace or embarrassment or humiliation. They know the rules of
Face the Nation
Meet the Press
, but nothing here is controlled.

Michael J. Fox was your first guest. Who would you like for your last guest?

A 70-year-old Michael J. Fox.

Why is
The Daily Show
advertised as “the most important show ever”?

It’s a haven, an oasis of serenity and sanity. It’s a new Statue of Liberty. It’s a bully pulpit. We have an enormous effect on the population. The power is incredible. I hadn’t planned to say anything about it, but we did a story about a peace accord in Kosovo, and the next day it happened. Coincidence? I don’t think so. I liken myself to Oprah. When I plug a book, it flies off the shelves. Where would
Tuesdays With Morrie
have been were it not for our recommendation? Where would Stephen King be today? We saved his career.

Speaking of careers, though the press and public love you on
The Daily Show
, Jon Voight, when he was a guest, ribbed you good-naturedly about aiming higher. Did that bother you?

No. I’m paid more money than I should be to come in, read the newspapers, write a bunch of jokes and work with an unbelievably talented group of people who make me laugh. It’s better than being on a sitcom, where the show can be a big hit but your character has a terrible story line and nobody likes you.

Like Jeff Conaway on

Right. Everybody else goes off to these monster careers, but he ends up on
Babylon Five
. The last time I saw Jeff I was on the road, flipping channels in a hotel room. He and two strippers were learning how to do something in one of those flicks you pray for when it’s late at night and the only thing on HBO is an old fight. It was some crazy titty movie. No dishonor in that, though.

In a recent
New York Times
story, Madeleine Smithberg, who helped create and runs your show, said that since Craig Kilborn left, the show “has lost the crystal-clear joke that it’s a parody of the news.” It wasn’t a complaint, but what did she mean?

They’d brought in an audience while Craig was there. An audience means you’ve given in to the fact that it is also a comedy show. When I came aboard I pushed that a little further. I don’t say outright that we’re doing jokes, but I ad-lib in a way that lets people at home know we’re enjoying ourselves.

You seem more conspiratorial than Kilborn.

That’s my philosophy of television. If you’re going to watch me, I might as well let you know I know you’re watching. I don’t think of this show as elitist.

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