Graduating from Virginia's College of William and Mary in 1984 with a degree in psychology, Stewart staged puppet shows for disabled kids, worked as a contract administrator at City University ("like working in cement") and tended bar. Though he'd always had a knack for generating jokes, which he calls "a brain dysfunction that you're trying to take to your advantage," it was not until 1986 that he finally moved to New York and made an assault on the comedy clubs, dropping his last name – allegedly because MCs mispronounced Leibowitz (in New York comedy clubs?) but actually, he has hinted, because of lingering paternal frictions. He soon became a fixture at places such as the Comedy Cellar. "I, like almost every other female in the comedy community, had a crush on him," says Janeane Garofalo, one of the other up-and-coming comics in the late Eighties stand-up boom. "He's just one of those guys everybody likes." Garofalo remembers Stewart as an incisive social critic, but he didn't "hit politics especially hard" in his act, she says. Back then his stuff hinged on what he calls "the holy trinity of comedy: sex, religion and death." When the first Gulf War broke out in 1991, Stewart was less likely to attack the politicians and the media than to make wry, Seinfeldian observations about the three-day ground war. "They were afraid this was going to be another Vietnam," he told audiences, "and it turned out it wasn't even another Woodstock."
But it was perhaps precisely such polite, prime-time-friendly joking that landed Stewart his first huge break, in 1993: his own talk show on MTV, The Jon Stewart Show. A year later the showwas syndicated. But Stewart proved singularly ill-adapted to a standard talk-show format. He seemed in pain, shrinking ever deeper into the cushions of his armchair. There seemed to be no way to turn it around. "It was a talk show," he says. "Am I suddenly going to discover some unbelievably interesting way of talking to Maria Conchita Alonzo?" It took a year for the show to die – slow torture for Stewart. "That show was a watershed," Stewart says, "and I don't mean comedically. I mean emotionally. I was playing scared. I was playing not to lose." Stewart would remember this when he got The Daily Show. But first he had to negotiate four years in the comedy wilderness.
Well, not wilderness. He was ferociously busy, appearing on Letterman and Leno, doing clubs, writing for and performing on The Lorry Sanders Show, penning a book of comedic essays and appearing in a few forgettable movies: The Faculty, Playing by Heart, Big Daddy – a career, come to think of it, that most comics would die for. Except that Stewart had once been considered a potential heir to Letterman's throne. Instead, he'd watched Conan O'Brien get the nod for Dave's Late Night slot on NBC, and in December 1998, he saw Craig Kilborn beat him out for The Late Late Show on CBS. Stewart was now in his late thirties. To avoid the ignominy of the "What Ever Happened to . . ." segment on ET, something had to happen.
What did happen was that in January 1999, he took over The Daily Show anchor chair that Kilborn had vacated. The show, under Kilborn, had parodied the news but with an emphasis on celebrity mishaps and a frat-boy knowingness wholly out of step with Stewart's persona, interests, talents — and brains. Two minutes in Stewart's company shows you that he's scary smart, and not the faux smart so familiar from fast-talking celebrities who have learned a few snappy lines about current events. And that's not to say that Ben Affleck isn't a nice guy. But Stewart actually thinks about stuff. Serious stuff, and thinks about it critically and deeply. And that's what he decided The Daily Show platform offered him: a chance to say something that mattered, with Styrofoam and rhythm. Only problem was, he was inheriting an entire production team and writing staff schooled in the fine art of making jokes about supermodels. Asked how he managed to retarget the show's comeadic arserial, Stewart says, diplomatically, "It was — frustrating, but over time the people that were less enthused about the direction of the show left, and we hired other people who were maybe more inclined."
The most crucial new hire was Ben Karlin, a then twenty-eight-year-old former editor of the satirical fake newsweekly The Onion, who was lit up with angry passion and fiery idealism — plus, he was funny as hell. Like Stewart, he had zero interest in writing japes about Pee-wee Herman's mug shots. "The main thing, for me, is seeing hypocrisy," Karlin says. "People 'who know better saying things that you know they don't believe.'" Stewart recognized a kindred spirit and Karlin was hired as head writer. "Ben was huge," Stewart says. "That was, for me, the beginning of it starting to take shape. When you feel alone, all it takes is one other person to go, 'I think that's right.'"
Now equipped with an agenda of closely tracking the actual big news events of the day, The Daily Show truly began to hit its comic stride with the 2000 election, whose protracted chad-counting outcome provided endless fuel for Stewart and Karlin's satiric indignation. Their coverage of "Indecision 2000" ("Choose and Lose") won a Peabody Award, and ratings began to climb. The next milestone was the attacks of 9/11, in the aftermath of which Stewart wasn't sure he could make comedy. But he went back on the air nine days later and delivered a tearful nine-minute monologue that, today, he would as soon forget. "It was cathartic and selfish and whether people related to it or not wasn't even so much the issue as we needed — or I needed — to clear my own head," he says. Karlin admits that, as head writer, he was worried. "It seemed there was no possible way we could engage the story." But they did engage it, brilliantly, in part by focusing on the worst excesses of the real media. Parodying the TV news show's despicable habit of conferring a jazzy entertainment-style title on every event, The Daily Show called its post-9/11 coverage "America Freaks Out," and its parody ticker read "Oh God Oh God Oh God . . . "
But it was in the lead-up to the Iraq war, in the winter of 2003, when The Daily Show began to do what it does best: attack the media for failing to aggressively pursue the truth from politicians. Nothing gets up The Daily Show team's nose like the 'way the media gave the Bush administration a free ride as it prepared for war last year, lobbing puffball questions to Bush at carefully scripted press availabilities, and then parroting, with no critical analysis, obvious falsehoods. "If you asked, they'd say their job is just to report and it's not their place to put in opinion," says DJ Javerbaum, the show's current head writer. "But that's a cop-out, and deep down they know they've been bullied."
Stewart thinks much of the problem is sheer laziness. "If I worked in a twenty-four-hour newsroom, all I have to do is find a liberal and conservative and I've done my job," he says. "I can lazily go, 'This is the question. Donna Brazile, what do you think? Bay Buchanan, is she right? Thank you, that was a marvelous discussion.' That wasn't a discussion." Indeed, Stewart gives the conservative Fox News Channel credit for at least having a point of view. "Some of their [broadcast] is an honest reaction to what they believe is a political and social point of view that is underrepresented, and some of it is a political strategy to retain power for those people," he says. "But what CNN does is far more of a missed opportunity, because they're not driven by anything." So is Stewart's point that liberals need a twenty-four-hour channel to counter Fox? Hardly.
"People say, 'The left wing needs a new station!' No they don't. We need a news organization that puts country over partisanship – that doesn't define truth through that bi-chromatic prism that is right and left." He points to the inanity of the Crossfire-style argument shows. "The overwhelming majority of the country is far closer than what shows like Crossfire would have you believe. But in the world of commerce, extremity is rewarded. Ann Coulter is not rewarded for writing thought-provoking columns. She's rewarded for saying, 'Joseph McCarthy was good people.' So then Michelle Malkin goes, 'OK, I'll see Joseph McCarthy and raise you the internment of Japanese people as a positive step.' So then the left has to come out and say, "We fought Afghanistan to build a pipeline from Uzbekistan.'" Stewart's point is that in a fevered media environment where the spoils go to whoever can make the loudest, and most outrageous, argument, the loser is the American public – and a democracy whose health is dependent on being properly informed by its watchdog media.
"I think what has happened to the media is ambition and stardom have overwhelmed purpose," he goes on. "People always talk about how there's a liberal bias and a conservative bias. But the main bias of the news is personal ambition, because a lot of choices are made based on not burning this source or not causing a conflict in an area that is your ladder upward. In the same way that there's no such thing anymore as a news interview with a newsmaker, because the 'get' is so intense. When Barbara Walters got Monica Lewinsky, that wasn't going to be a newsmaking interview because she had to seduce Monica Lewinsky into the interview. You're not going to get anything controversial because: Why would Barbara do that to a friend? The media is utilized purely as a strategy by people in power."
Sounds good – except for one uncomfortable fact. As political operatives on both sides have recognized the importance of wooing The Daily Show's plum demographic, Stewart finds himself being held to a new standard in his own interviews. This was never more apparent than on the evening of August 24th, when he scored a major "get" – a one-on-one with Democratic presidential candidate John Kerry. In faceoffs with Republican strategists such as Ed Gillespie and Marc Racicot, Stewart has proved himself a polite, but tenacious, interviewer. (His genial carving-up of Republican Rep. Henry Bonilla was a classic that should be studied in journalism classes.) But with Kerry, Stewart seemed to fall prey to precisely what he attacks in the likes of Barbara Walters: soft-soaping a "get" toward whom he feels sympathetic. The encounter was often excruciating, with Kerry demonstrating all the charm of a cadaver, and Stewart overawed, nervous and eager to please. Sample exchange:
STEWART: Are you the number one most liberal senator in the Senate?
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