Angry Optimist: The Life and Times of Jon Stewart

CHAPTER 5

WITH HIS SCHEDULE changed from working seventy-hour weeks to zero, Stewart finally had a chance to think about what he really wanted to do. He decided to take his time figuring it out. He toured the country performing stand-up at the kinds of hole-in-the-wall comedy clubs that he had appeared at before he hit the big time. He also started to sift through the increasing number of offers that came in, ranging from movie deals to subbing for talk-show host Tom Snyder, who was at the helm of The Late Late Show.

Despite his new relationship with McShane, he decided to move to Los Angeles in order to develop these new opportunities, though he was understandably reluctant about leaving the New York area, where he had spent his entire life aside from college. He liked the fact that for the most part, New Yorkers didn’t much care about celebrities.

“Everybody’s got their own shit to worry about,” he said. “I think that as long as I keep the music down, they’re fine.”

But sooner or later, Hollywood beckons many New York–based comedians and actors, and Stewart was no exception. And when Snyder offered him the chance to occasionally substitute for him on his late-night show, Stewart decided to head west.

Snyder was a veteran talk-show host who had hosted Tomorrow with Tom Snyder from 1973 through 1982. With his background in hard news, the show had an inquisitive, thoughtful style, though his pointed questions were also interspersed with Snyder’s opinions and comments; it was almost like watching two people hold court in a living room, punctuated with occasional sparring. Then, after more than a decade away from sitting behind a talk-show desk, Snyder had signed on to The Late Late Show in 1995, which was launched by David Letterman’s production company Worldwide Pants as a way to hold on to viewers after his own show ended at 12:35 A.M. The irreverent Snyder was a great choice for that time slot and he would helm the show until the spring of 1999.

Stewart first sat in for Tom Snyder in the fall of 1996, and did so well that he became a regular substitute host, filling in every three or four months, usually for a week at a time. The difference in height between the two hosts—Snyder was six four to Stewart’s five seven—provided for some memorable moments.

“The cameras [and furniture] were designed for his frame, so when I got there I looked like [Lily Tomlin’s] Edith Ann character sitting in the chair,” said Stewart. “They had to give me a booster cushion. So whenever I was working that show, I was actually sitting on a children’s pillow.”

And he sometimes acted like a kid, breaking into The Price Is Right studio with his friends after hours, where they took turns spinning the big wheel that served as the cornerstone of the game show.

Yet he felt like he could never totally relax and be himself while guest hosting. “When I was doing The Late Late Show with Tom Snyder, it was like house-sitting. So while it’s nice, because it’s a nice place to house-sit, you’re still a little worried like, ‘Oh my God, I just got ashes on the couch. Now what am I going to do?’ You don’t want to be the guy to fuck it up for when the other guy comes back and goes, ‘Who drank all my whiskey?’”

Even though it was common knowledge that Snyder wouldn’t stay on more than a few years because he wanted to retire, and some speculated that Stewart would make an ideal replacement, Stewart let it be known that it wasn’t in the cards. He was hesitant to commit to another talk show so soon after the failure of The Jon Stewart Show at Paramount.

He took advantage of being in Los Angeles to branch out in his entertainment career. And just like after all the odd jobs he held after college, Stewart figured he might as well try everything. He hit the ground running, and then some.

He signed a deal with Miramax Films with his recently launched Busboy Productions company, which he named for one of the many part-time jobs he had held through the years. The pact committed Stewart to star in at least two film projects per year and offered him the chance to write and produce as well.

And even though he said he’d never do a syndicated show again, Stewart also signed a development deal with Letterman’s Worldwide Pants company to eventually host and produce his own late-night talk show, one which would be totally on his terms where he wouldn’t have to kowtow to a large entertainment company’s executive brass.

It didn’t take long before Stewart picked up small roles in popular TV shows like The Nanny and NewsRadio, and taped a couple of live stand-up performances that were later broadcast by HBO, including Jon Stewart: Unleavened. He also appeared in a number of small parts in movies where he appeared alongside some of the biggest stars of the time.

He thought his first big break would come in the 1996 movie The First Wives Club playing opposite Goldie Hawn, but his scenes ended up being deleted from the film. He followed that up with a role opposite Drew Barrymore in the romantic comedy Wishful Thinking, which also came out in 1996. The story was told by jumping between several different points of view—including Barrymore’s and Jennifer Beals’s, the other female lead—and turned mixed and missed signals into well-trodden jokes. Stewart played a nebbishy third or fourth wheel who in the end became Beals’s love interest. To no one’s surprise, least of all Stewart’s, the film went straight to video.

Half Baked came next, where Stewart had a cameo role—billed as “Enhancement Smoker” in the end credits—of the cult stoner movie starring Dave Chappelle. The movie is about a group of pot-smoking friends who have to come up with the money to bail a buddy out of jail after he accidentally kills a diabetic police horse by feeding it junk food. Reviewers regarded it as the ultimate pothead film. Stewart followed up that role with another small part in Since You’ve Been Gone, a made-for-TV movie starring David Schwimmer about a disillusioned group of friends attending their tenth high school reunion.

Next up was the romantic comedy Playing by Heart—the original title was Dancing about Architecture—which featured a series of interlocking stories and a top-notch cast, including Sean Connery, Angelina Jolie, and Gillian Anderson. Here, Stewart’s role was a bit meatier, as he played an architect named Trent intent on courting Anderson’s man-shy character.

In all of his roles, Stewart’s lack of acting chops was evident. It wasn’t until he got the chance to play a different kind of role in the 1998 movie The Faculty, a flick about a group of high school students attempting to stave off an alien invasion, that it appeared he finally loosened up and looked like he was enjoying himself. Stewart played a biology teacher named Professor Edward Furlong who along with fellow actors Salma Hayek, Bebe Neuwirth, and Usher, of all people, is transformed into an alien after being infected with worms from space. One reviewer advised viewers to “Think of it as Invasion of the Body Snatchers enacted by the cast of Scream, an enjoyably dumb B movie.”

Stewart’s performance in all of these movies was unremarkable, a fact that he fully recognized. “The truth is, I’m not a good actor, but it’s fun to try,” he admitted.

“I trusted these people. I was hoping that they knew what I could do, and that was okay with them. I didn’t go from being a talk-show host to being Sean Penn, I just went to being in a movie. I really felt like I didn’t mess up, but I am really proud of it because I feel that I didn’t mess up. I wasn’t the burnt kernel in the popcorn. In that sense, I felt really proud of it that I held my own in this situation.

“[A]ll you can do is show up on the set,… and hope it works out. And then you go home and write your own stuff.”

Some felt that Stewart’s background as a stand-up comedian hurt his chances at succeeding in the movies. “While it’s something that a lot of comics try to do, it’s really hard to be able to play a role when people look at you and think of you as yourself,” said Joey Bartolomeo, a senior writer at US Weekly. “If you look at someone like Jerry Seinfeld, his only role has been as Jerry Seinfeld on TV. You don’t see him in movies playing other parts.”

At the same time, Stewart credited his talk-show experience with helping his acting more than doing stand-up. “When you do stand-up, so often you’re the only person on stage and it’s all your thing,” he said. “It’s very gladiatorial. Obviously, when you’re in a scene with somebody, you’re supposed to listen and react—and that’s a bit of a transition.”

“As a stand-up comic, you don’t work with other people,” he noted. “As host, you’re hanging on to every word people say because you have to react to it.”

“It’s nerve-racking to be with people who know how to act,” he added. “Most comedians are doing themselves, ten percent angrier or happier. I like being able to do a little stand-up and do something else and also try acting. It’s that neurotic vision: the more things that I can do, the more employable I’ll be in the future.”

While busy acting, he also started to miss doing stand-up. “I think comedians have this Pavlov’s dog response when it comes to jokes,” Stewart said. “You tell a joke, you get a laugh—and I miss the immediacy of that. With a movie or a book, you have hours of wringing your hands, wondering if people thought it was funny.”

He was more of a natural in his occasional appearances on Dr. Katz, Professional Therapist, an animated show that ran on Comedy Central from 1995 to 1999, but that was only because the show revolved around comics performing their routines while sitting on a psychiatrist’s couch.

And then his most natural role appeared on the horizon in the form of The Larry Sanders Show on HBO, where he essentially played himself, a younger comedian who was being actively groomed and encouraged to replace an older mentor on a late-night talk show, played in the series by Garry Shandling.

Though he welcomed the steady gig, Stewart had misgivings about playing the role. “It’s really one of the most uncomfortable places you can be,” he said of his real-life predicament. “I think I realized I’d rather satirize who I am than be who I am.”

Stewart appeared on several seasons of the show from 1996 through the last episode in 1998, and along the way as Shandling-as-Sanders spoke about leaving the fictitious show on some of the episodes, Stewart’s character was rumored to step into the host’s shoes on the show. Though Stewart played himself on the show, he acknowledged that the show’s version of himself was rougher and ruder than how he presented himself on his own talk show on MTV and Paramount.

“But to play that character, I really couldn’t play myself. I needed the protection of the character to do the awful things the character would need to do.

“At first, I was playing me, but not well,” he said. “Then, in the last season, I got a full-blown story line and a chance to go outside myself. And to make it work, I really had to stretch.”

Instead of just showing up for a segment or two for a few episodes each season, since the network executive characters on the show were trying to push Sanders out while grooming Stewart to succeed him, the real Stewart not only had to spend more time on the set but he also had more lines. Lines that required him to act rather than just crack jokes, which was what most of his movie roles had consisted of so far. For instance, once Sanders and his producer Artie—played by veteran actor Rip Torn—got wind of the executives’ plans, several episodes revolved around the two backstabbing Stewart while they pretended that it was business as usual.

After his movie roles had gone nowhere Stewart started to sift through the deals he had made with both Miramax and Worldwide Pants. Though Miramax had broached the concept of a weekly sitcom, Stewart nixed it. “I was of the mind that, unless it was a great idea, I didn’t want to do it,” he said. “Just to do it for the sake of doing it wasn’t a good idea. No one needs another halfhearted attempt.”

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.”

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 Winstead 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.”