Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  With Letterman’s company, talk turned again to a late-night talk show to come after The Late Late Show with Tom Snyder. But he was hesitant to try to replicate what he had done previously. He was thinking of writing a book, and just didn’t want to tie himself down to another long-term television commitment. In the end both the Miramax and Worldwide Pants deals expired. Afterward, he went back on the road, on Comedy Central’s nationwide Stand Up for Sanity tour.

  Stewart had found that he liked pursuing several different projects at the same time rather than having one full-time gig. “Admittedly, at some point I’m probably going to have to settle down and sort of pick a discipline and stay with it for a little bit of time, but right now it’s kind of nice to be able to float around and do a bunch of different things,” he said.

  As a result, one magazine writer called him “the celebrity equivalent of lint: he pops up in interesting and unlikely places.”

  There was also his growing discomfort in Los Angeles. A diehard New Yorker, he missed his girlfriend, Tracey. Their long-distance relationship had turned more serious. So he began to pull away from Hollywood with an eye toward returning to the East Coast.

  * * *

  The year 1998 would turn out to be a pivotal one for Stewart, and not just because he hosted a Sesame Street TV special called Elmopalooza, where he helped a variety of Muppets celebrate the thirtieth anniversary of Sesame Street.

  For one, he was filming Big Daddy, a movie with hit potential that was shot in New York; it would hit theaters in June of 1999. When the project first came along, he didn’t think much of the part, or the movie, for that matter. But it did give him a chance to work alongside his old stand-up buddy Adam Sandler, who had come up in the clubs of New York at the same time.

  “I always used to try to borrow money from Adam when he was making fifteen bucks a night,” said Stewart. “He was a soft touch.”

  Stewart played the role of Kevin Gerrity, roommate to Sandler’s thirtysomething slacker Sonny Koufax. One day, Kevin surprises Sonny by dumping his five-year-old son at their apartment while Kevin flies to China for a business trip. Stewart turned the part from what could have been an extremely unsympathetic character into one with depth and wit.

  “Jon had the trickiest part in the movie,” said director Dennis Dugan. “He’s in the first twelve minutes of the film and in that short amount of time, he has to make enough of an impression … so that when he returns at the end, they’ll go, ‘I’m so happy that this guy came back!’ And Jon achieved that.”

  Jon Stewart at the film premiere of The Waterboy, starring his Big Daddy co-star Adam Sandler, in New York, November 1998. (Courtesy BEImages/Matt Baron)

  Also in 1998, Stewart put the finishing touches on his first book. Though some expressed surprise at his desire to become an author, to him writing a book that consisted of a collection of comic essays was very similar to writing a series of interrelated stand-up routines.

  “I get the sense that it’s all the same thing, just in different forms,” he said. “I don’t look at it as that different.”

  Naked Pictures of Famous People would hit the New York Times best-seller list when it was published in September. But a month before that, Stewart received even bigger news:

  He actually appeared first on a list to take over a talk show. Not second.

  His old guest-hosting position on Tom Snyder’s show was coming to an end: once Snyder announced his retirement, Letterman scouted around for a replacement. As usual, Stewart’s name appeared on the short list, but in the end, Letterman chose Craig Kilborn for the job. Kilborn, who was then hosting a Comedy Central show called The Daily Show, accepted the position. Yet again, Stewart was second banana. However, with Kilborn’s move the Daily Show spot had opened up.

  “I always had my eye on [The Daily Show],” said Stewart. “But it’s kind of funny, it’s musical chairs. There are only five of these jobs available.”

  Kilborn had hosted the show since the launch of the half-hour program, designed to “report” on news of the day by giving it a satirical twist. He’d cut his teeth as a sports anchor, first at a Fox station in Monterey, California, and then as an anchor on ESPN’s SportsCenter. Comedy Central had ordered The Daily Show into production to replace Bill Maher’s show Politically Incorrect, which had switched networks to ABC.

  When The Daily Show debuted on July 22, 1996, it was structured like any local newscast you could switch on anywhere in the country. Kilborn served as the news anchor, reading a few national news stories, which were followed by a few in-studio segments and field pieces from a correspondent or two. Since The Daily Show billed itself as a fake-news show from the beginning, the correspondents’ stories followed suit. But the set’s appearance fit the format.

  “We just told the designers we wanted something that Ted Koppel would want for Christmas,” said writer J. R. Havlan, who joined The Daily Show in 1996 when Kilborn started as host.

  With Kilborn moving to take Snyder’s job, there was an empty host’s chair to fill at The Daily Show. Madeleine Smithberg, a producer who had worked alongside Jon on his previous show at Paramount, was now working at The Daily Show, and she thought Stewart would make a good host.

  Stewart was under consideration—yet again—and he expected to come in second place as he had numerous times before. But he got one of the biggest surprises of his life when Comedy Central executives offered him the job. In addition to being The Daily Show host, he’d also share a co-executive producer credit. They struck a deal, signing him to a four-year contract paying him $1.5 million a year.

  “There was only one name that came up,” said Comedy Central president Doug Herzog. “We found the most talented free agent in the market.”

  “Jon will have a wider appeal to a greater age and gender,” agreed Eileen Katz, senior vice president of programming at Comedy Central. “There’s something that’s more accessible about Jon as opposed to that whole National Lampoon school of comedians and hosts that looked very Ivy League and Midwest.”

  Many critics looked forward to his debut—and to getting rid of Kilborn. They—along with viewers—disdained Kilborn because of his almost constant smirk and frat-boy approach that infected the overall tone of the show and theme of many of the sketches. “He’s certainly witty enough and articulate enough to host his own show, especially if he’s replacing a guy like Craig Kilborn,” said Adam Buckman, a TV columnist at the New York Post. “Jon’s actually more talented at this sort of thing and can come up with funny things off the top of his head.”

  Stewart was ecstatic, and viewed the job as “sitting around with funny people, banging out jokes, and creating a television show. I have no hobbies, no outside interests,” he said. “I’m fine with spending fourteen hours a day putting a show together with tape and string.”

  At the same time, he was realistic enough to know that his chances for longevity were not in his favor. “Whenever you take over something that is popular and has a fanatical following, you’re never going to please everyone,” he said. “The trick is to have enough wherewithal to follow through with what you want to do with it and give it time to evolve.”

  For once, he had come in first. But he had his work cut out for him. There had been a definite tension on the set, specifically between Kilborn and co-creator Lizz Winstead. Even though Winstead had been heavily involved in the initial development of the concept of The Daily Show, she had not been involved in the final decision about the show’s first host.

  “I spent eight months developing and staffing a show and seeking a tone with producers and writers, but somebody else [hired Kilborn],” she said. “There were bound to be problems since I viewed the show as content-driven while he viewed it as host-driven.”

  Eighteen months after the debut of The Daily Show, things had only gotten worse. In a 1997 Esquire magazine interview Kilborn made a few negative comments about the women who worked at the show, even calling them “bitches.” He also said that he knew Win
stead would “do a Monica Lewinsky” on him. When the magazine came out, the network suspended Kilborn for one week. Winstead quit shortly afterward.

  Even with Winstead gone, the atmosphere on the show remained toxic. Several reviewers thought both Kilborn and the correspondents were working overtime to be nasty. “The take-no-prisoners attitude of this headline-oriented, half-hour sarcasm-and-shtick program [is] a slick combination of Saturday Night Live’s Weekend Update segment, moronic frat-house interplay, political humor, and surrealistic nonsense,” said one.

  Kilborn could be shockingly mean on the show. In 1997 the sentence was handed down in the 1993 World Trade Center bombing, and on air, Kilborn said the Twin Towers were occupied with a surfeit of stockbrokers. “Officials speculate that if the bombing had gone according to plan it would have taken a quarter of a million lives—and ten or twenty souls,” he added.

  “In the world inhabited and delineated by The Daily Show, everyone is an idiot,” a New York Times reviewer wrote. “It’s like making fun of the people in line at Epcot: too easy, but darned satisfying when you’re cranky. And the central characters seem to have no idea that they’ll be savaged when the piece is edited.”

  Correspondent Stephen Colbert started working for the show in 1997 and tried hard to keep away from the tension, yet he had misgivings about the tone of the stories he was called to report on. “You wanted to take your soul off, put it on a wire hanger, and leave it in the closet before you got on the plane to do one of these pieces,” he said. “We had deep, soul-searching discussions on flights out to do stories, saying, ‘We don’t want to club any baby seals, I don’t want to hold this person down and kick him in the teeth comedically.’ But sometimes it would happen, because you had to come back with something funny.”

  For the most part, he stayed out of the fray. “I was so new there that I was kept completely out of any sort of political machinations there,” he said. Even so, what did he think of Kilborn?

  “He was really good at reading the teleprompter,” said Colbert.

  Even though he was stepping into an established show with a staff who were used to doing things a certain way, Stewart had already made up his mind that he was going to break away from the format and shake things up a bit. First and foremost, he wanted to make a difference in his own way.

  “I decided not to give a crap about what anybody else thought anymore [and to do] what I wanted to do, with like-minded people who’d bring passion, competence, and creativity to it.”

  The truth was that critics didn’t expect much from his new gig. In fact, one even viewed The Daily Show position as a step down for Stewart. “He once seemed destined for more,” said the reviewer.

  To start, he was the antithesis of Kilborn, who had a vain streak a mile wide; in between segments, Kilborn would compulsively fix his hair and makeup. When asked if he’d do likewise, Stewart said absolutely not, cracking, “There are no mirrors.

  “The tone will obviously be a lot more Yiddish,” he said. “I think at some point, I’d love to have a little bit of diversity. But as I keep saying, there is a certain mind-set that won’t develop until I get there.”

  With that said, Stewart’s neurotic streak reared up when asked what he’d think if the show would succeed. “I’m doing everything I can to sabotage my career,” he said. “It’s a little thing called fear of success, but really, a regular talk show can become your life. For ten years, it’s your life. That is what you are and what you do.” At the same time, he welcomed the challenge. “[The Daily Show] is a different kind of hosting than I’m accustomed to, it’s a little less free-form, but we’ll find out what I can do well and start tailoring it to that.”

  When Kilborn left, two other Daily Show regulars decided to exit as well: correspondents Brian Unger and A. Whitney Brown. Since Stewart’s style was more of a mensch than the nasty guy that Kilborn played, Stewart believed that his more-optimistic outlook would have a top-down effect, spreading to the writers. But at the same time, he didn’t want to rule anything out. “Hopefully the only things off-limits are crummy jokes, but being a stand-up comedian, I know that’s not always the case,” he said. “You know it when you have to take a shower afterward.”

  * * *

  Despite industry speculation that he took the Daily Show job so that he could continue to do the occasional Hollywood movie, that was not his motivation. For one, the contract expressly specified that he couldn’t take on a non–Daily Show gig for the first year, but it was clear—between the long days of sitting around on a set to the fact that he didn’t really like acting—he just wasn’t cut out for making movies.

  It was rumored that Kilborn wanted to take a few of the Show’s segments with him to The Late Late Show, including the “5 Questions” bit, where the host asked his five rapid-fire questions. However, because Kilborn had broken his contract with Comedy Central, the legal team was much less inclined to negotiate with him. And so “Headlines,” “Back in Black,” featuring longtime contributor Lewis Black, and “A Moment of Zen” all stayed with the show.

  To Stewart, it didn’t much matter. He wanted to develop his own segments.

  “You wouldn’t want to take over for Letterman and start doing ‘Top Ten’ lists either,” he said. “My feeling is basically the show’s identity is going to have to evolve once I get in there. I’d love to have a little bit of diversity. Not just celebrities, but newsmakers.”

  “The structure of the show is very sound, so it’s really a question of finding different flourishes,” he added. “For the first few months, I’m sure I’ll be stumbling around like when you first work in a restaurant. I’ll be looking for where the ketchup is.”

  CHAPTER 6

  WHEN JON STEWART debuted as the new host of The Daily Show on January 11, 1999, the critics were pleased.

  “Happily, it was no trial to watch,” wrote one reviewer. “A welcome return.”

  “Comedy Central did not lose in this game of late-night musical chairs,” said another. “Stewart is more likable and less self-satisfied than Kilborn, and the show’s satire is smart enough to have real sting. Now if only Daily could expand to an hour and allow Stewart’s celebrity interviews to run longer than four breathless minutes.”

  “Stewart can barely keep a straight face delivering the nasty punch lines, and the disparity between his mildly neurotic persona and the show’s gleefully raunchy tone seems to add to all the irony,” wrote another. “I often still hate myself for laughing, but with Stewart, I forgive myself more easily.”

  Once the opening credits ran, Stewart took a deep breath and looked into the camera before announcing, “Welcome to The Daily Show. Craig Kilborn is on assignment in Kuala Lumpur, I’m Jon Stewart.”

  He then launched into a rapid-fire mix of the old routines while giving hints of his new approach and desperately trying not to alienate loyal viewers of the Kilborn version, which more often than not, tended toward frat-boy-style humor and pranks.

  He interviewed actor Michael J. Fox while wearing a suit—a definite step up from the jeans and sweatshirt ensemble that had served as his nightly wardrobe on his previous talk shows—and admitted that he was more than a little nervous. “Honestly, I feel like this is my bar mitzvah,” he said to Fox. “I’ve never worn something like this, and I have a rash like you wouldn’t believe.”

  After the interview, correspondent Stephen Colbert weighed in with a report on the impeachment trial of President Bill Clinton and fellow correspondent Beth Littleford interviewed four of the original munchkins from the Wizard of Oz. In all, Stewart’s first appearance set the tone for how the show would proceed in the future, as well as how it would be radically different from the program during the Kilborn era.

  But the timing put him right in the crosshairs; not only were people watching to see how Kilborn’s successor would excel—or flunk out—but also there was an enormous amount of material he had to work with, much like the political cartoonists who love it when things in Washi
ngton go awry.

  While cast and crew maintained that the change in tone and content would be gradual, the truth was that with such a huge change and attitude at the top, it took only days for the audience to notice. For one, since Stewart was clearly more interested in politics than Kilborn, the show started running more political stories the very first week.

  While correspondent Stephen Colbert had long considered himself to be apolitical, he experienced a radical shift once Stewart took over. “[The show] switched from local news, summer kicker stories, and celebrity jokes, to more of a political point of view,” he said. “Since Jon has a political point of view, he wanted us to have one, too. I’ve always been a news junkie but I never wrote political satire before The Daily Show,” said Colbert. “I didn’t enjoy political humor until I started working on it with Jon, and then I found that I had a stronger one than I had imagined.”

  Conversely, over time, Stewart would find that working day in and day out on the show actually made him less political. “The more time you spend with the political and the media process, the less political you become and the more viscerally upset you become at the inherent corruption,” he disclosed.

  Yet Stewart didn’t hit people over the head with the political content, instead suggesting to producers and writers that they try to shape correspondents’ stories so that they had more of a connection to the news; after all, from the start, The Daily Show was billed as a news show, albeit a fake one. One of the complaints that correspondents had when Kilborn served as host was that the dichotomy between the news stories and correspondent reports was pretty radical.