The Daily Show (The Book)

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This Just In

JON STEWART, The Daily Show host, 1999–2015

At the time, I was obviously making my mark in such films as Wishful Thinking and Dancing with Architecture, or Dancing About… Oh, no. They ended up calling it something else. Playing by Heart, I think it was.

JAMES DIXON, manager for Jon Stewart, 1987–

After The Jon Stewart Show was canceled by Paramount, he was… not burnt on being on TV, but he wanted to kind of wet his feet with film. We had this nice deal with Harvey Weinstein, and Jon was down in Tribeca and he's getting to kiss Angelina Jolie in films.

JON STEWART

Getting fired from Paramount was the real turning point for me. Because I thought that after appearing on Letterman, now I'm a made man. And the Paramount thing, I thought losing it meant I was an unmade man. I realized you still have to make your act better. The goal is to produce, the goal is to make things.

So I spent some time writing and performing on The Larry Sanders Show, and I learned a lot from Garry Shandling.

JUDD APATOW, standup comic, writer, director

Garry had the foresight to write about the talk show wars and this very subtle aspect of it, which is, you support a young comedian and slowly the network likes him more than it likes you, and then that younger guy, in ways that he understands and might not understand, slowly pushes you out of your job. Similar to what really happened with [Jay] Leno and Conan [O'Brien] and [Jimmy] Fallon. So there was a moment when Garry was considering continuing The Larry Sanders Show, and changing the name of it to The John Stewart Show, with an H so it wouldn't really be Jon. Everyone was excited about it for a while, but it went away.

JON STEWART

Probably my favorite Garry memory is his life being so bizarre to me. It was going to Warren Beatty's house with Garry and having dinner with Warren and Sean Penn in this beautiful mansion on Mulholland or wherever it was, and then heading down to the Chateau Marmont. And at this time, Warren Beatty's got to be fifty, sixty years old and Garry's not a spring chicken, and we're in the Chateau Marmont surrounded by fans, if you know what I mean.

I knew I didn't want to live in LA. Because everything is inflected with show business, and I found that to be suffocating. Even your Saturday basketball game over at Garry's house. It was a red carpet of people that you couldn't help but think, "Oh, wow. Look at me, I just got my shot blocked by that guy from The Avengers," or whatever it was. You always felt a little bit like you were on an audition, and I never liked that feeling.

JAMES DIXON

Worst-case scenario, he could always be a writer-producer on his own or on someone else's show. We didn't say, "Let's host a news parody show." Jon was always smart about the long play.

JON STEWART

The Daily Show wasn't necessarily on the radar. I think they called and said, "Hey man, would you be interested in talking about this?"—something along those lines, something as romantic as that.

JAMES DIXON

I definitely advocated for him to do it. I just said to him, "You can put this through your prism. You can make it smarter and different than what it's been." Now, I definitely didn't see the show becoming the political lightning rod that it evolved into.

J. R. HAVLAN, writer, 1996–2014; member, original Daily Show staff

I knew of him as a sort of leather-jacket-wearing, hipster young dude who was different from the personality that we had been working with, let alone created, for The Daily Show, for Craig, the newsman thing.

KENT JONES, writer, 1996–2001; member, original Daily Show staff

Oh, it was really positive, my reaction to Jon being hired. He was a name, and he had a good reputation. Hiring Jon is Comedy Central saying this is an important show to them.

LEWIS BLACK, contributor, 1996–

From the time I met Jon in the clubs, I liked him, he was funny. There was no bullshit to him. Hiring him for The Daily Show made sense. The only thing I found disturbing was that they auditioned everybody, and they didn't audition me. And you just do that out of etiquette. You don't have to hire me. I don't care. You don't have to put film in the camera. You just pretend that you're allowing me to do this.

DOUG HERZOG, executive, MTV, 1984–1995; president, Comedy Central, 1995–1998; executive, Viacom, 2004–

In the summer of '98 when we announced that Jon was going to take over The Daily Show, we had a little press conference in the lobby of the old Comedy Central offices. And Stephen Colbert showed up, as a member of the press representing The Daily Show, wanting to know why he didn't get the job.

STEPHEN COLBERT, correspondent, 1997–2005

"You told me he wasn't funny." That's what Jon said to Doug Herzog.

The Daily Show offices and studio were in a still-rugged pocket of Hell's Kitchen, at 513 West Fifty-Fourth Street, between Tenth and Eleventh Avenues. The Daily Show's neighbors were abandoned warehouses, but the building itself was a cozy, three-story, redbrick townhouse. The production offices were upstairs, with the one-hundred-seat studio on the ground floor.

JEN FLANZ, from production assistant to executive producer, 1998–

The area was rough in those days. I think Adriane Truex got carjacked outside the Fifty-Fourth Street studio.

Jon's first day, he walked around and introduced himself. He was wearing a black leather jacket. I remember hearing rumors before he started: "He doesn't want to wear a suit." Our wardrobe girl at the time was upset. Jon did wear suits on the show. It was fine. But it was a big thing at the time.

MADELEINE SMITHBERG, The Daily Show cocreator; executive producer, 1996–2002

Because of the point of view that had been created by Craig Kilborn sitting in the chair, the writers' role had inflated. Yeah, they were spoiled rotten, because almost every show in late night is talent driven. They got too big for their britches.

STEW BAILEY, from field producer to co–executive producer, 1996–2005; member, original Daily Show staff

Madeleine had hired me as a segment producer on Jon's MTV pilot and then on the series, and then also on The Daily Show when she started with Kilborn. Jon came into Daily Show writing meetings originally and would listen. I think that he really wanted to make sure that he understood what the process was as opposed to coming in and immediately dictating terms.

JON STEWART

A couple of months before I officially started as host there was a meeting with the writers and producers. Let's call that "Jonny's surprise party." I knew that the people working on the Kilborn show were rightfully proud of it. It had done well. It was not the sensibility that I thought was right for me, and so when they approached me for the show, I was pretty clear about the direction I thought I wanted to take it. Seemed like everybody was on board with that, and so this was my first chance to meet with all the people who, I had been told, were so excited about that. So excited. They're so happy you're here.

And I walked in, and it was a room full of people who, as it turned out, were annoyed that I had an idea about where I wanted to go, who thought that I was going to MTV it up. I was told, "This isn't about bands. We do a real show here." I just sat there like, "Oh, fuck." It felt a little bit like, "Wow, none of this was in the brochure. The brochure said that this was oceanfront property."

JAMES DIXON

I had to talk Jon down. Not from a tree—from a skyscraper. Because they basically said to him, "Welcome aboard. This is how we do shit here. Grab a chair." It was bullshit. And Jon had to systematically mold the show piece by piece, person by person.

MATT LABOV, publicist for Jon Stewart, 1994–2008

The stakes for Jon were fairly high at that point, because he's not a superyoung guy anymore, and he's had shots, and people easily disappear and go into the woodwork. He didn't get the Conan job on NBC, he didn't get the 12:30 job after Letterman. If this doesn't work on fucking cable, then where would Jon have ended up?

PAUL RUDD, actor

Technically I was Jon's first Daily Show guest interview. I went to the University of Kansas, and my roommate, Stewart Bailey, became a segment producer who was with the show from the very beginning. I'd been on Kilborn's Daily Show. When Jon replaced Craig, they wanted to do a test show so Jon could get used to the format. I was wearing my girlfriend's Jon Stewart Show MTV T-shirt.

Stewart made his debut on Monday, January 11, 1999. His first joke was that Kilborn was "on assignment in Kuala Lumpur." His first headline, "The Final Blow," was about the Senate impeachment trial of President Bill Clinton. His first guest was Michael J. Fox, then starring in ABC's City Hall sitcom Spin City. But Stewart looked, for the first months, very much the guest himself. Other than a new couch and desktop—and blue script pages for Stewart to scribble on portentously, replacing Kilborn's white paper—the set design was unchanged. The theme song, Bob Mould's "Dog on Fire," was the same. And Stewart's suits were so ill-fitting that they looked inherited from his much-taller predecessor.

J. R. HAVLAN

You watch his first shows, where he's wearing David Byrne's suit, you can see that it's the exact same format. He didn't want to change anything, at least at the beginning.

The first joke I wrote that Jon did on the air was on his first day. Popeye and Olive Oyl were getting married. We showed a picture of them, and you see Popeye, with his huge forearms. The joke is, "As for the wedding night, Olive Oyl had only one request: no fisting." The crowd loved it. But when I go back and I look at the tape, I can almost see Jon falling to pieces inside his own head, like, "Maybe I should change things up here sooner than I was planning."

Recurring segments from the Kilborn days—like "Ad Nauseam," about dumb commercials—continued to appear regularly during Stewart's first year. And there were wince-inducing bits, including one with Stewart singing, "Homeless, homeless, man," to the tune of "Macho Man," in a piece about the destitute former lead singer of the Village People. There was also a headline taking crude potshots at flimsy Florida targets.

Stewart did not arrive with a precise blueprint for where he wanted to take The Daily Show. But he did have a clear idea of the sensibility he wanted to instill. One of Stewart's comedy heroes was George Carlin, who wove social criticism into his jokes and riffs about dirty words, organized religion, and hypocritical politicians. Stewart wanted to give his Daily Show a similarly substantive foundation—and, crucially, he wanted it to "punch up." He started shifting The Daily Show's sights to target powerful people and institutions, and he began changing the tone of the show from randomly coarse to deliberately barbed. Not that he was opposed to making a good dick joke now and then.

ADAM CHODIKOFF, from researcher to senior producer, 1996–

It was pretty quick that things changed. One of Jon's lines was, "No more Carol Channing jokes"—the celebrity stuff. Instead of doing six headlines a show, we started doing three headlines a show, but they were more intense. They were longer and had more power and research to them, and more tape.

JUSTIN MELKMANN, from segment producer to supervising producer, video department, 1997–

During the Kilborn era, it was about "How can we seem like we've gone too far?" With Jon, we went from creating the news—creating funny spoof headlines—to making fun of the news. That was a big change.

JON STEWART

You can satirize news media conventions just by embodying the form in slightly exaggerated or subtle ways—for instance, the way that they do those camera turns. Making the story itself have purpose—that's when I felt we got something.

For me the key switch was relevance—turning the machine in a direction more toward politics, media, satire. The first two years, most of my energy was spent saying, "I understand that's a funny joke, but our point of view here is not that the lady who is selling the Barbie in that commercial is a whore. That joke runs counter to the idea that we are maybe looking at the underlying sexism involved in this product."

MO ROCCA, correspondent, 1998–2003

Shortly after Jon arrived, the whole staff piled into Madeleine's office. We had done a bit about Dana Plato dying, and Jon felt bad about delivering a joke when the end of her life had been so pathetic. He said he had resolved that the show needed to have a point of view and couldn't just be the kid at the back of the classroom throwing spitballs in all directions. I remember people trading the kind of glances that said, "Oh shit, this is going to be a disaster."

JON STEWART

To be fair to the writers who stayed from Kilborn's show, they had a successful thing going. They thought of it as a continuation of their show. I thought it was a new show. To me it wasn't edgy or provocative to just take napalm to a bush for no reason. You wanted it to be pointed, purposeful, intentional, surgical.

I felt like I walked in there with a very open "Okay, so this will be great," and it was "Hey, motherfucker, you came here to kill a baby."

KENT JONES

Well, I would not agree with that. I don't remember any of this being as hostile as it has been portrayed, I just don't.

J. R. HAVLAN

A month or two in, you could see flashes of pieces and jokes that have meaning, which has always been Jon's thing. That's what Jon instilled in everybody that came through there: "I'm not interested in the first thing off the top of your head. You're saying it before you've given thought to what it is you really want to say." That was the biggest learning process with working for Jon. It takes you away from being surface.

To change the culture of The Daily Show, though, Stewart knew he needed committed allies as much as he needed people who could write funny and fast.

CHRIS REGAN, writer, 1999–2006

I was thirty-one and I had been working as an advertising writer for Sony Music. It was a good job for someone trying to start a comedy career, because it was a company where they spent an awful lot of money, I had a big office, and I didn't do much in the way of actual work.

I got ahold of the fax number at SNL [Saturday Night Live] for Colin Quinn, when he was doing "Weekend Update." Every Friday, I would fax stuff to him, and he began to buy a decent chunk of jokes from me.

Jon took over The Daily Show, and he asked Colin Quinn if he knew of anyone who was writing decent topical stuff, and Colin gave him my name, which is awfully nice of him because I'd never met Colin.

I was called in by Madeleine Smithberg and Chris Kreski, who was the head writer at the time, and I had an interview with them. Jon came in only at the very end. He was eating Chinese food out of a Styrofoam tray. I think he had sweat clothes on: a gray sweatshirt and gray bottoms. He looked like an old-timey police cadet.

Jon just sat down on the couch, while he was eating, and he asked me one or two questions, and then said, "So, if we hire you here, are you going to be my guy?" And I wasn't quite sure what being "his guy" entailed, but I was very eager to get out of advertising, and I said sure, and then I was hired about a week later. I was Jon's first hire on the show.

JON STEWART

Six or eight weeks in, the writers called me into their office. They're like, "You can't change our jokes anymore." I didn't know what to say.

So after a weekend of pacing and smoking and having tremendous Lincoln-Douglas debates on the couch by myself, I went back in, and it was horrible. I basically told them all to fuck off. "You work for me. And if you don't like the direction, okay. I get that. Don't work here."

There were points where I thought, "I made the wrong decision. I've got to leave." But I don't give up very easily. It was open hostility, which is so enjoyable. It became that sense of "Okay, let's arm-wrestle." This will give you a hint of my personality of grudges.

CHRIS REGAN

It was tense. It was a weird experience to be involved in, because it was the first job I'd had in the industry, and I just kind of wanted to lay low and do my work. But there was a lot of conflict between Jon and the Kilborn writers. As time went on, it put into perspective the "Are you going to be my guy?" question Jon had asked me.