Angry Optimist: The Life and Times of Jon Stewart

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 conservative 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.

As he pondered the offer, however, the network pulled a fast one and instead took the offer to Jimmy Kimmel, who pounced on it. At the time, Kimmel had just launched his own talk show on ABC, Jimmy Kimmel Live!, after serving as cohost of Win Ben Stein’s Money and The Man Show, which aired on Comedy Central in the late 1990s.

Amazingly, despite the accolades and his now iconic status, Stewart still came in second. However, this time he didn’t seem to mind. The truth was that as his star continued to rise, Stewart retreated further inward whenever he was away from the studio. He was gracious with fans whenever approached, offering up an autograph and sometimes a joke, but otherwise he went into deep retreat whenever he wasn’t at the studio. Indeed, one reporter called him “a high-functioning hermit.”

In the early 2000s when it seemed the rest of the country was attached to their computers and the era of smartphone ubiquity was just around the corner, Stewart still didn’t have an e-mail address, at home or at the studio. “Don’t you find that people contact you way more?” he responded when someone asked the reason why. Indeed, he is rarely seen on the Manhattan celebrity circuit, only emerging to make the obligatory appearance at the annual awards shows where he’s been nominated. Stewart is a content homebody, and once he found a kindred spirit in Tracey—whom he married in 2000—he had little reason to stray from his favorite activities away from work: doing the daily Times crossword puzzle, watching TV, and taking the dogs—he had added another pit bull named Monkey to the household—to the park.

“I was a fan of The Little Rascals and Petey was a pit, so maybe that was inherent,” said Stewart. “If you go to the store and buy the generic ‘dog,’ that’s the dog. That little block head and that little dog body, and so energetic and playful. They’re meaty and muscular and fun.”

And then an interesting thing began to happen. Word on the street and at many college campuses was that many young people who never watched network news were watching The Daily Show regularly and considering it their primary source of news, particularly when it came to the 2004 presidential election season.

“I’m not watching the evening news to figure it out, that’s for sure,” Joe Harper, a twenty-one-year-old college student, commented in early 2004. Instead, he relied on Dennis Miller, Bill Maher, and The Daily Show to get his information. “I trust these guys,” he added. “Their stuff is funnier, but it’s also truer.”

Harper was in good company. A 2004 survey released by the Pew Research Center revealed that fully one-fifth of Americans aged 18 to 29 said they relied on not only The Daily Show for their main source of news about the presidential candidates but Saturday Night Live as well.

Comedian Miller weighed in. “I don’t think kids even vaguely connect to guys like [Peter] Jennings and Dan Rather,” he said. “If you’re an eighteen-year-old, who are you going to trust to give you the facts? Dan Rather in that epaulet jacket where he’s just about to go fly-fishing after the show, or are you going to listen to Jon Stewart? Of course, you’re going to listen to Jon.”

“It sounds a little bit apocryphal to me, but we do repackage the news, so I suppose that we are a valid source as long as people can understand when we’re goofing and when we mean it,” said Colbert. “I think you have to have some handle on what’s happening in the world to get our jokes, because we only do the most cursory explanation of what the issue is in order to set up our punch lines. We don’t talk in depth about any stories. I suppose you could watch our show and sort of get a sense of what’s going on in the world, but you’d also be missing half of our jokes.”

“I find it hard to believe,” said Stewart. “I enjoy the show as much as the next guy, but we don’t actually give any news. If you haven’t seen the news, you probably won’t know much about what we’re talking about. We’re a cable channel. I mean, we’re beyond Spanish people playing soccer on the dial, we’re near a naked talk show. My guess is if you found your way to us, you’re a relatively savvy consumer of information.”

“Different outlets have been saying that for a while or claiming studies [demonstrate] the show’s influence on the public,” said writer J. R. Havlan. “We don’t sit around thinking about it. We don’t come in and say, ‘How are we going to affect the media landscape? Are we going to increase the number of kids who get their news from The Daily Show?’ There’s no insidious plan.”

If anything, the show teaches viewers to think and dissect the news that’s presented to them, regardless of the medium. “The show provides people a lesson in skepticism,” said Havlan. “That’s the biggest service. I mean, we’re not even interpreting things, I think it’s more truthful than that. Network news—not just cable—has to be constantly questioned, and our show is uniquely positioned to do that.”

For his part, Stewart discounted the studies and surveys. “I’d be awfully surprised given the magnitude of media available,” he said. “Younger people are far more inundated with information than we ever were. We’re suffocating in information.”

And when it came to deciding which stories to cover—after all, with a twenty-four-hour news cycle, there are always plenty of stories out there that just beg to be satirized—there are additional issues to tackle, among them responsibility to the story and the culture. “We try to cover stories that are interesting to people and, more importantly, relevant,” said Karlin. “I think we’d be a lot more into finding something that’s inherently funny and quirky, but then we[’d] have to educate the audience a lot more. Instead, we’d rather talk about what’s on people’s minds or what’s particularly absurd of this moment or of this time.

“We try not to measure the reaction to the show as much as our own internal barometer,” he added. “I don’t want to take the temperature of how people are receiving it, because I think that would affect how we’re producing it. When we see something we find absurd or interesting, we try and write jokes about it or come up with something interesting to say about it.”

As the ratings continued to climb, politicians began to notice that an appearance on the show could boost their visibility with a younger demographic virtually overnight. Though some might shudder at the idea of being interviewed or featured in a story on The Daily Show, others embraced the opportunity.

“Politicians love him and they respect him because he is a very intelligent guy,” said Neil Rosen, entertainment critic at the New York Times. “But I also think they do the show because they understand that it is a very smart audience that is watching. They are also an audience who votes. And as soon as you walk onto that set as a politician you have adopted [Stewart’s] credibility.”

However, that comes with a caveat: for the most part, the politicians who flocked to the guest chair opposite Stewart were Democratic. Republicans started to complain, but Stewart maintained that he never hesitated to lash out at hypocrisy in the Democratic Party when the opportunity presented itself. He also thought that politicians made for more sparkling conversation than actors, musicians, or authors in many cases.

“I just think politicians are more interesting to talk to,” he said. “Not that I’m not fascinated with the exact date a movie is coming out, but in general, I think it’s slightly more interesting probably to talk to somebody who does something completely different from what I do.”

At the same time, given the tone of the show as well as the format, if they weren’t promoting a book or movie the majority of people who agreed to go on the show did so to make a specific point. “People don’t typically come on our show unless they’re disgruntled,” Stewart said. “Then they come on the show to express their disgruntlement. We are the last stop of the disgruntled.”

For this reason, they also made easy targets, though Stewart maintained that he always tried to resist the lazy joke. “The show is not a megaphone,” he said. “You can’t end every joke with ‘Let’s bomb the motherfuckers,’ even though that’s how I feel. But I take some pleasure in just ridiculing al Qaeda. When we got the Kandahar tape”—the video released in December 2001 in which Osama bin Laden confessed to being the mastermind of the September 11 terrorist attacks—“our first instinct was to… lay down fart noises,… because he hates to be laughed at.”

Little was sacred when considered for their crosshairs, and even Comedy Central basically left the show alone. One of Viacom’s top brass actually referred to the show as “the latchkey kid.” One of the few hard-and-fast rules they ran into was that “dildo” couldn’t be mentioned in a show four times; but three was okay.

“Humor is such a subjectively weird genre,” Stewart said. “One man’s meat is another man’s poison, it’s so hard to say this is what’s allowed, but this isn’t. So we vacillate. Some days our heels are planted firmly in the ground and we’re ready to fight, and other days we’re washing our hands thirty times because we think we have anthrax.”

All the while he was determined not to cater to the lowest common denominator. It just wasn’t his way. “There’s a certain school of comedy that mistakes edge for the obnoxious. I find that the best comedy, the most edgy stuff, is rooted in a way of thinking about something that other people haven’t come to yet. To me, that’s edgy.”

Surprisingly, advertisers didn’t mind when they fell victim to Stewart’s criticism. “If the show is going to go after an advertiser, we call the advertiser with a heads-up, but we tell him, ‘If Jon is making fun of you, it’s a plus,’” said Larry Divney, president of Comedy Central in 2002. “It means you’re being talked about!”

Besides, the exposure could be worth it. Three years after Stewart took the helm, seven hundred thousand people were watching the show each night; Kilborn had barely half the viewership. In January 2005, The Late Late Show with Craig Kilborn morphed into The Late Late Show with Craig Ferguson after Kilborn decided not to renew his contract and left the program.

For his part, Stewart’s role as host and executive producer meant he was tired all the time, especially due to his habit of micromanaging every last detail, not only of the show but also of the employees. “He asks about every tiny detail of things that are important in your life,” said Smithberg, “and he isn’t feigning. He knows the eating habits of everyone, and he knows when all the camera guys are pooping.”

And then came September 11, 2001. Perhaps Stewart’s finest moment came in a moment of horror and poignancy and great uncertainty for the future of The Daily Show.

It had seemed like just another Tuesday morning. He and Tracey had recently celebrated their first wedding anniversary, and he was getting ready to head uptown from their Soho apartment to the studio to start working on that night’s show when he heard a thundering crash.

Then he looked out the window and saw one of the World Trade Center towers on fire. Twenty minutes later, they grabbed the cat carriers and a few belongings, and evacuated their apartment, heading uptown.

And then a horrible thought occurred to him:

How could he be funny at a time like this? And how could the show possibly continue?

“Everyone was so scared and on tenterhooks,” said Brian Farnham, editor-in-chief of Time Out New York. “How could you be funny about something that was so terrifying? Jon Stewart and The Daily Show were one of the first shows to say, ‘You know you can make fun of anything if you do it the right way.’”

“It was a fragile time for everything,” Stewart acknowledged. “People talk about the Holocaust as the greatest inhumane times. But my guess is that even at Auschwitz people were telling jokes. It’s human nature to find light in darkness somehow.”

During the first week after the terrorist attacks, the networks and many cable channels pulled their regularly scheduled programming to focus on airing news updates and live broadcasts from Ground Zero. On September 17, David Letterman was the first of the late-night talk shows to return to the air. The Daily Show went back on the air on September 20, and Stewart began the show without the music, without the roaming cameras, and without the wildly cheering audience.

It was one of the best monologues of his life, which he delivered in a stilted yet straightforward manner without his typical slightly ramped-up tone. Throughout the almost nine-minute talk, Stewart occasionally had to pause to regain his composure. The funny man was nowhere in sight. “They said to get back to work, and there were no jobs available for a man in the fetal position,” he said. “We sit in the back and we throw spitballs—never forgetting the fact that it is a luxury in this country that allows us to do that.

“The view from my apartment was the World Trade Center. Now it’s gone. They attacked it. This symbol of American ingenuity and strength and labor and imagination and commerce and it is gone. But you know what the view is now? The Statue of Liberty. The view from the south of Manhattan is now the Statue of Liberty. You can’t beat that.”

He’s said that he only watched the segment once, and that he vowed never to watch it again, it was too painful.

Over the nine days that the Show didn’t air, a quarter of viewers passed up the reruns and switched to channels that offered more hospitable comfort-food kinds of shows, like Nick at Nite. But after the new shows resumed, not only did regular viewers return but new ones watched as well, in part because Stewart was intent on serving as a teacher of sorts, to teach viewers about certain elements of this strange new fragile world while still conveying it through the lens of humor.

And his image and influence changed from that point on.