Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  Said David Hinckley, critic-at-large at the New York Daily News, “It actually serves a legitimate news purpose in my night. It is another reinforcement of what people are talking about because it has a pretty good pulse for what’s on people’s minds.”

  Bob Schieffer, host of Face the Nation on CBS, had this to say: “Jon Stewart is to television what the editorial page cartoonist is to the editorial page of newspapers. The editorial page cartoonist is the only person at the newspaper who is allowed to lie. I see Stewart as an editorial page cartoonist. A lot of time, by taking something beyond where it is, it helps you to drive home a point and really understand the truth.”

  Indeed, compared with the other late-night shows, The Daily Show was different not only in tone but in format. “Basically, Letterman and Leno have to get through those ten-minute opening monologues [while] the fuel of their shows is often more guest-driven,” said Stewart. “[By contrast], we had to fill our half-hour every night with something. Not that those four minutes with [guests like] Tiffani-Amber Thiessen aren’t enjoyable. Don’t get me wrong, she tells a hell of a story. But I think we would go insane if we had to spend our whole day trying to think of synonyms for dumb, if we hadn’t looked for larger arcs in the comedy.”

  Another reason why he and the producers decided to keep a guest segment in each show was for sheer utility: it absolved the writing staff from having to develop another five or six minutes of jokes and routines.

  Though Stewart had his own ideas as to why people reacted so strongly to the show, in the end, every monologue, sketch, and interview came down to what he cared about most and how he wanted to convey that to his audience. “I think for me in some respects I am attempting to scratch an itch,” he said. “And I want to make humor about things I care about. And unfortunately, the larger issues are probably more deeply affecting to me than most things.”

  CHAPTER 7

  THE WHOLE TONE of the show had shifted in the year since Stewart came on board as host. Whereas previously, stories about Bigfoot and taxidermied squirrels would have automatically been green-lighted, now the future of such pieces was uncertain. “As soon as the presidential campaign started up in 2000, you could see the show begin to change,” said Colbert. In fact, at the end of the 2000 campaign season, Colbert—newly politicized—offered up a bet to the other correspondents and producers. “I put a hundred dollars on the table and said to the field producers, if you can get us a Bigfoot story, I’ll give you the hundred-dollar bill,” he said. “I knew none of that shit was going to get past Jon anymore. Everything had to be grounded in reality, in something that’s happening in the world, so we could use our field pieces as an addition to the satirical take that’s happening at the desk.”

  “Some of the correspondents on The Daily Show write more than others, some are more traditional performers, but in almost all cases input is pretty welcome,” said Karlin, “anything that can help make it in their own voice. Colbert is the most experienced writer, so he writes or rewrites a lot of his own stuff.”

  With the first year of The Daily Show with Jon Stewart under his belt—and very positively received—in early 2000 Stewart felt he could finally bring out the big guns and turn more of the focus of the show to politics. Then again, with the upcoming 2000 presidential election, he had little choice. And given the tone of his commentary and stories in the first year, Stewart’s own political leanings were no secret.

  “I’ve always felt [that] what is defined as leftist [is] relatively reasonable,” he said.

  “I have a tendency to lean toward the underdog, which I assume is the liberal perspective,” he acknowledged, “but as I’ve gotten older, I find I’ve developed my own ideology. I don’t really fit into anything.”

  “In the beginning of 2000, the content became far more political,” said writer J. R. Havlan. “When the election came up, we were in a unique position, and Jon realized this is what we’re here for. That’s when we started to focus on media coverage.”

  Just as Stewart’s visibility and reputation were starting to achieve critical velocity, the 2000 presidential election cycle began. Certainly there was no better place to exercise his muscles and to make a statement than at the party conventions in 2000. “We are definitely a fake news show, and political conventions are definitely a fake news event,” he said. “So, in some respects, we’re probably the only news organization who should be here.”

  In fact, choosing to call the Show’s coverage of the 2000 campaign and election season Indecision 2000 was a brilliant stroke of genius that at once sent a message of what viewers could expect as well as mock the stance of more conventional news media. However, when they first came up with the moniker, no one on the staff of The Daily Show, least of all Stewart, had any idea how prescient that term would turn out to be, as the results for the November 7 elections were still not determined even after a month of a contentious round of recounts was conducted in Florida, which had been too close to call, and until the U.S. Supreme Court stepped into the fray and basically called the race for George W. Bush.

  But viewers were noticing how Stewart’s election coverage was radically different from the shows their parents watched. In fact, for The Daily Show’s Indecision 2000 election night special, almost as many younger viewers tuned into Comedy Central as those who were watching the results come in over at Fox News. The Daily Show measured 435,000 viewers aged 18 to 34 compared to 459,000 in the same category at Fox. Since Stewart took over as anchor the previous year, The Daily Show averaged two million viewers a night, which was huge for cable and significantly higher than Kilborn’s numbers, which typically hovered around one million.

  Though Stewart scorned both parties in almost equal doses, he held special rancor for how the media reported the campaign and its aftermath, failing to hide his disgust. “This isn’t Olympics boxing, it’s a presidential race,” he said. “[The media] set up expectations in that first debate as, literally, if George Bush proved he could feed himself, that was presidential, and if Al Gore blinked, he had warmth. And that’s the way they judged the debate. They didn’t even deal with the fact that when an issue did come up, George Bush’s proposals were literally, ‘I think Americans are good. And should help themselves.’”

  The uncertain outcome of the election fanned the flames of The Daily Show, attracting thousands of new viewers to the show since it could rightfully be argued that the hanging chads and circus-like atmosphere of conventional news reports helped not only to develop Stewart’s chops but also to build a loyal audience that would stick around long after the winning candidate had settled into the Oval Office.

  “Everything [in the campaign] became so absurd that the absurd people became the actual pundits,” Smithberg said. “Jon Stewart is now a kind of recognized, viable pundit.”

  “There was no better story for us than the 2000 election because it involved everyone, it was unprecedented, and no one died,” said Colbert. “The night that Gore conceded, we were finally able to use the material we were writing for thirty-two days. It was so much fun to release all that comedy that had built up for that time. I couldn’t imagine having more fun. We all felt that way.”

  More important, the Show’s coverage of the convention helped put both the show and Stewart on the map. “[I]n the year 2000 Jon Stewart officially became a public intellectual,” said Robert Thompson, director of the Bleier Center for Television and Popular Culture at Syracuse University.

  “We’ve always wanted to be less dependent on the Hollywood cycle of standard talk-show guests,” said Ben Karlin. Though it had been tough to convince name-brand guests to come on the show for a couple of years, it finally turned around. Again, Karlin credited the campaign season. “The show made a name for itself during the elections as a place where politicians or journalists would want to come and talk.”

  For his part, Stewart mixed his opinions with a caustic humor, and had this suggestion for future election seasons: “I think what we should do at five
P.M. on election night is all walk outside and raise our hands for one of the two candidates and just have a helicopter fly over,” he said. “I just think it would be easier. The idea that some people vote on machines and other people pick a bamboo stick that’s shorter than another, the whole thing is ridiculous.”

  The hard work and notice were recognized the next year when the show won a prestigious Peabody Award, given to broadcast outlets to recognize the best programs of the year. Other winners that year included The West Wing and The Sopranos and single episodes of 48 Hours and Dateline NBC.

  Everyone who worked on the Show improved their game even more, spurred on not only by the national recognition but also by witnessing their boss’s work ethic. “I was shocked at how much thought and distillation he personally puts into the script,” said Colbert. “His care and unbelievable work ethic, and ability to consume information, digest, and distill a story. He’s telling us that this is the mechanics of the human interaction, and this is the actual message of the story.” Colbert, perhaps more than the other correspondents, took to heart Stewart’s palpable disdain for the traditional news media and used it to help shape his own character. “He’s naming what seems most ridiculous about the news, which is the personalities and the news itself,” Colbert said. “It’s only the overt game that’s being reported.”

  During the 2000 campaign season, while The Daily Show began to gain critical mass among viewers, traditional media began covering the show itself. During the days leading up to the election, news shows on the networks—like the Today show—were running brief segments from the previous night’s episode on a regular basis. “It’s like they’ve handed over the reins of commentary and reporting to comedians because we’re the only ones who can make sense of it,” said Madeleine Smithberg. She and other staffers had mixed feelings about their newfound standing. “Our currency is one of insanity. Stop giving us credibility! We don’t know what to do with it, it’s messing up our shtick.”

  What happened next was entirely predictable, if not a bit uncomfortable: the major news programs and networks started to invite Stewart onto their programs to boost ratings and appeal to a younger demographic than usual. His reluctance to make the rounds was not just due to the early hour.

  “It’s weird to be anywhere at seven thirty A.M., that’s when I should be fast asleep with my dog,” he said. But there was another, more important issue. He felt that when he was interviewed by traditional media people—particularly on TV—that while they didn’t strictly treat him as a comedian, they didn’t quite take him seriously either. “The difference between myself and the analysts on a show like Today is when I’m introduced, they either say, ‘Now for a look at the lighter side of politics,’ or, ‘Comedians have been making hay with this election, for that take…’ It’s never Gore’s speech that sets up my segment, it’s Jay Leno’s joke.”

  In a sense, Stewart wanted it both ways: though he always maintained he was a comic first and not a newsman, he took issue with his treatment on the major news networks and programs, when they did regard him as “just” a comedian.

  After all, in the two years between the first time he hosted The Daily Show and the show where they announced that George W. Bush would be the new president, Stewart had come a long way. And since he didn’t even try to hide his disdain whenever he appeared on a network news show, in many instances his appearances combined light chitchat with a bit of finger pointing followed by the inevitable and uncomfortable silence from his on-air hosts.

  But perhaps the thing that got him incensed the most was when his on-camera interviewers disclosed to him off-camera that they envied him. “The thing that shocked me the most was when I first met reporters who would tell me, ‘Boy, I wish I could say what you’re saying.’ You have a show! You’re a network anchor! Whaddya mean you can’t say it?” he said. “It’s one reason I admire Fox. They’re great broadcasters. Everything is pointed, purposeful. You follow story lines, you fall in love with characters: ‘Oh, that’s the woman who’s very afraid of Black Panthers! I can’t wait to see what happens next.’”

  The next statement might surprise his fans. “Fox News and our show have a tremendous amount in common,” he said. “We are both reactions to the news and to government and … expressions of dissatisfaction.”

  Stewart made no secret of his disdain for CNN. “Their version of clarity seems to me to be like grits without salt. It’s just all mashed up—there’s no direction, under the guise of ‘integrity.’ I can never figure out what the hell I’m watching,” he said. “With other networks, you either agree or disagree with how they do stuff, but CNN feels like an opportunity squandered.”

  However, some news stars were absolute fans, and Stewart didn’t mind them as much. After CNN anchor Wolf Blitzer taped a segment for the show, Jon asked if he could hang out for a bit. Blitzer quickly agreed. “How could I say no?” he asked. “This is the most important show ever.”

  “There’s no doubt he’s an important fact of life in this current political environment,” Blitzer said. “Off camera, he’s a very politically aware news junkie.”

  In Stewart’s eyes, his exchanges with TV interviewers seemed like a hall of mirrors. “On television,… operatives for both political parties will say, ‘John Kerry’s the most liberal’ or ‘The jobs created are nine thousand dollars less,’ and nobody ever says, ‘Where do you come up with these numbers?’”

  This desire to press until he gets a clear answer came out loud and clear when former Republican congressman Henry Bonilla came on the show and Stewart asked him how his party came up with the formula where they declared that then-senator John Edwards was “the fourth most liberal senator.” Bonilla didn’t answer the question and the line between what Stewart does and what journalists do became further blurred when Stewart complained that most TV journalists don’t question their guests like he does.

  He didn’t work to hide his contempt for politicians on the show, though he directed his producers and bookers to bring more of them onto the show. “If you feel like comedy program bits are your best effort as far as selling your candidate, good luck to you,” he said.

  “These people are salespeople,” he added. “Instead of rotisserie ovens they are selling this idea of preemptive war or social-security reforms.”

  At the same time, he declared a basic tenet of the tone of The Daily Show that he’d repeat many times in his own defense. “We’re not provocateurs, we’re not activists; we are reacting for our own catharsis,” he maintained. “There is a line into demagoguery, and we try very hard to express ourselves but not move into, ‘So follow me! And I will lead you to the land of answers, my people!’ You can fall in love with your own idea of common sense. Maybe the nice thing about being a comedian is never having a full belief in yourself to know the answer. So you can say all this stuff, but underneath, you’re going, ‘But of course, I’m fucking idiotic.’ It’s why we don’t lead a lot of marches.”

  Of course, this was a completely fresh take on TV, whether it was his show or the more traditional news programs on cable or network, which underscored another reason the shows had for booking him: “These guys have twenty-four hours to fill,” he said. “They’ve got to come up with something. If these guys did what they should be doing, forty-five minutes into their newscast they’d turn to the other guy, say, ‘I’m out of here,’ and then they’d leave.”

  But Stewart found it more difficult to hide his disgust at a new and rapidly growing trend in the news media: in the wake of the Gore vs. Bush debacle, some of these shows actively introduced a style of program that was most prominently on display on the CNN show Crossfire, which pitted two people with diametrically opposed viewpoints and let them go at it on live TV. Stewart hated this format because he felt the shows were based purely on opinion with little to do with real news value.

  “It’s the WWF,” he said. “These shows are all about conflict. Whatever the situation is, they take a liberal pundit and a con
servative pundit—the more extreme the better—and let them yell at each other. It doesn’t reflect anyone’s opinion. It doesn’t matter.”

  If anything, his disgust with both sides was hard to hide, and actually turned the self-proclaimed liberal into a voice for the moderate middle, at least temporarily. “We’re moderates!” he proclaimed. “Moderates never mobilize quickly. Moderation doesn’t inspire passion. That’s the thing about being a moderate. You’re not the person standing outside the voting booths in Miami/Dade County to stop people from doing the recount. Moderates have a life. Or they’re home cleaning the gutters or something.”

  * * *

  Despite Stewart’s contempt for much of the news media, it continued to flock to him, bestowing him with honors and awards and inviting him onto more shows and programs, as well as to host awards shows. He agreed to some offers, including the Grammy Awards in both 2001 and 2002.

  He was obviously thrilled when The Daily Show won accolades from establishments he actually respected. The Daily Show won an Emmy for Outstanding Writing for a Variety, Music or Comedy Program in 2001, and Jon felt that somebody out there finally respected him. In addition to winning the same Emmy for writing for the majority of the next decade, The Daily Show would also proceed to win an Emmy for Outstanding Variety, Music or Comedy Series each year for the next decade starting in 2003, an unprecedented feat.

  And then, the old world started to knock on his door again. Just as Stewart’s four-year contract with Comedy Central was coming up for renewal in 2003, David Letterman started to float rumors that he was thinking of moving his show to ABC when his own contract expired. As before, Stewart’s name was considered as a possible replacement, but now with his own star in ascendance and so many people clamoring for a piece of him, there was little chance that he would ever come in second place again. In the end, Letterman stayed put at CBS, but intriguingly, ABC upped the ante and offered Stewart his own late-night show to shape as he wished.