Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  Stewart wholeheartedly agreed. “Twenty-four-hour news networks [are] where a lot of the satire lies. News holds itself to a higher plane … There’s a real hypocrisy about what these people have become. To see Barbara Walters criticizing a celebrity story when that’s what they’ve become … now it’s all confrontational.”

  “I have a lot of hostility [toward] the news media,” he added. “I have more trouble with the commentary on Clinton’s affair than Clinton’s affair. The self-righteousness is embarrassing.

  “The news now is like a children’s soccer game. Whatever the main focus of the day is where they go; it’s not about territory and positioning. When one kid has the ball, everyone runs over there. And then he kicks it and everyone goes over there.”

  Stewart was also starting to lose patience more often with the media than with politicians. “I’m less upset about politicians than the media. I feel like politicians, there is a certain, inherent—you know, the way I always explain it is, when you go to the zoo and a monkey throws its feces, it’s a monkey. But when the zookeeper is standing right there, and he doesn’t say bad monkey.

  “Somebody’s got to be the zookeeper,” he continued.

  Stewart was also not a big fan of the network newsmagazine shows like Dateline and 20/20. “You watch those shows and you’d think we were falling apart: ‘You won’t believe what’s in that cheeseburger!’ ‘Did you know that your airbag could decapitate you?’”

  But another distinct shift had taken place once Stewart took over. Previously the idea of the show being a total satire was a no-brainer. After Stewart came on board and put his spin on things, often in a sly, subversive way, it wasn’t unheard of for viewers to become confused and think they were watching an actual newscast. As Madeleine Smithberg put it, it was no longer “crystal clear that we were a parody of the news.

  “You really believed that Craig was that guy behind the desk,” she said. “He looked like everyone you’ve ever seen on TV. Jon Stewart has an unbelievable range of things that he’s capable of doing, but he delivers headlines like a guy telling jokes. He’s brilliant, but you don’t really believe he’s a news anchor.”

  And in that fashion, the line between fake news and real news became blurred. And the overhaul that Stewart performed on the show from day one clearly reflected his slightly embittered view not only toward life but toward the news as well. “[What’s funny about the news is] not the news itself but how the news is delivered,” he said. “The parody is our bombastic graphics and the news song, the correspondents and their interaction with me. By using the general structure of a news show, which we find inherently satirical, we’ve found a cheap way to get in twenty monologue-type jokes.”

  “Oddly enough,” he added, “The Daily Show is one of the most responsible news organizations because we’re not pretending to be news in the first place. Our one rule is, no faking.”

  Unlike traditional news media, The Daily Show wasn’t in the business of going out and finding news; instead, producers and writers only had to have the talent to review a day’s worth of news and then retell it to their audience while giving it their own unique spin.

  “One of the joys of being fake news is we don’t actually have to break news,” said Stewart. “We can just react to something we found interesting the day before.”

  “The more we pretend we’re a news show, the clearer our comedy becomes,” added Smithberg.

  There were other benefits as well: occasionally, the news itself made the writers’ jobs much easier: “[Sometimes] you don’t try to top it with a written joke, because just on its own it can be pretty ridiculous,” said Ben Karlin.

  For that reason, executive producer D. J. Javerbaum said no one ever worried about running out of material or missing a scoop. “It’s a reactive show,” he said. “As long as we’re given things to react to, we’ll be fine.”

  Indeed, as viewers and critics began to regard the content of The Daily News as journalism, Stewart was quick to correct them, with a caveat that took an interesting twist:

  “I don’t think what we do is journalism,” but rather “analysis because we don’t do anything but make the connections,” he explained.

  It was obvious from the beginning that the role of a fake news anchor fit him better than it did Kilborn, who was more interested in sports than the news. “I’m a little bit too obsessed with the news,” Stewart admitted. “I find the news easier to follow than narrative entertainment programs. But I find the news, for me, I watch it like a program. I can’t wait to find out what’s happening with my favorite characters, like, ‘Oh, I’m so sorry they dropped Saddam Hussein from the show. Oh, they’re bringing him back!’”

  He also discovered that he had missed having a regular mouthpiece for his opinions. “I’d not had a regular TV gig in three years,” he said, “and I realized when I was on Sanders that the ability to comment in sort of a timely fashion is terribly important to me. While I still comment on it, I usually do it in my living room, and you begin to think of yourself as perhaps that creepy, bitter guy who sits on his couch and says, ‘Can you believe this!?’”

  He also looked forward to doing a good chunk of the writing on the show, unlike Kilborn who was content to just sit at the anchor desk. “That’s really my favorite thing,” he said, “sitting in a room with funny people till somebody hits on just the right bit.”

  Stewart laid down the law the first time he hung out in the writers’ room, not only eliminating almost all of Kilborn’s sophomoric frat-boy humor and segments, but also about clarifying the mixed signals the show was sending. “Half the jokes were about Barbie as a bad role model for girls, and the other half were about how ugly the spokesmodel was,” said the new host.

  But for the first couple of months, despite the positive response from critics, Stewart thought he had made a horrible mistake in accepting the job. A month before the switchover, he walked into a meeting of writers and producers on the show that was clearly hostile.

  “I did not realize that a lot of the people who worked there were assholes,” he said. “I walk in the door into a room with the writers and producers, and the first thing they say is, ‘This isn’t some MTV bullshit.’ And then I was told not to change the jokes or improvise.” As soon as he left the meeting, he called his agent and told him to “get me the fuck out of this, these people are insane.”

  Indeed, within a few months, several writers who had been there since the beginning gave notice that they were leaving, though Stewart said that it took over two years before the naysayers on staff were totally gone. He was not surprised that they left, but at the same time, he wasn’t terribly upset either. “I can’t tell you how relieved I was when people started walking [because] I didn’t have to fire them,” he said.

  He hired Ben Karlin, who had written for the satirical newspaper The Onion, and he started working closely with correspondent Stephen Colbert.

  He made no bones about the fact that his overall aim was to convey the news through the filter of his worldview while never losing sight of the fact that first and foremost he wanted to make people laugh.

  He also wanted to work to make the tone of the show a bit kinder and gentler. “It’s fair to say that at times The Daily Show can be a little too mean,” he said of the show before he joined. “I happen to have a huge soft spot for all the eccentrics out there in America, and I think at its best, the show celebrates them.” At the same time, he wasn’t above knocking someone off a pedestal if it meant it would generate a big laugh. “The show is what it is, and if sometimes that means going out there and tearing Carol Channing a new asshole, well, I don’t have a problem with that.

  “Reality has gotten so absurd, it’s almost like you’re making it up, but as a comedian, [I’m essentially] cheering for the disillusionment of society,” he conceded. “I’m hoping for chaos that I can muck with. And I have the utmost confidence that the world will provide it. I’m not hoping for the apes and the monolith, but that
makes my job easier.”

  “Every day the world deals us a hand,” Smithberg agreed. “And we’ve built a machine that can cope with it.”

  At the same time, Stewart and the crew were totally open to reinventing themselves along the way, to toss out what didn’t work and to pounce on those segments that did. “This 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 … It’s less driven by me than the Paramount show was, but it will be ultimately driven by a certain comedic point of view that’s different.”

  Because his previous talk show had been canceled he was pretty laid-back about the prospects for the show’s failure, as well as his. But he was also pretty good at hiding the stress he felt. He had been a heavy smoker since his stand-up days, a habit he still clung to tenaciously. He liked to drink Coke from the bottle, and when the first one of the day had been emptied, he used it as an ashtray. When asked how many cigarette butts were in the bottle by the time he went home at night, he replied that he didn’t know, “and counting would take all the fun out of it.”

  But by all outward appearances, Stewart seemed pretty relaxed. “For me, a talk show was never really the goal,” he said. “People that worry about where they’re going next generally don’t end up where they think they’re going. I just worry about what I’m doing now and try to make it good. When you’ve got too much of a master plan, it’s going to fail.”

  * * *

  Once Stewart had settled into his job and the staffers became comfortable with their new direction, it was time to hire a couple of new correspondents since Brown and Unger, who’d left when Kilborn departed, hadn’t been immediately replaced. Producers wanted to be sure to match any new correspondents with the new direction of the show. They asked around the studio for suggestions, and Colbert suggested Steve Carell, who he’d worked with at Second City and on The Dana Carvey Show.

  In the meantime, Stewart had begun to transform the job of fake anchor—which Craig Kilborn had always delivered with a healthy dose of smugness—into something uniquely his own. Instead of conveying fake headlines with a huge wink to the audience as Kilborn had done, Stewart’s tone took on more of an inclusive air, more of a sense of being in on the joke, as if he were saying, “Can you believe these guys?”

  Even though the show was now The Daily Show with Jon Stewart, whereas Craig Kilborn’s name hadn’t appeared anywhere in the show’s title, one thing that viewers found refreshing about the show was that even though Stewart set the tone of the show, it wasn’t about him, but about his ability to share the absurdity of current events with an audience of people who could definitely appreciate it. “Jon Stewart has brought back a kind of an everyman intellectualism,” said Brian Farnham, then editor-in-chief of Time Out New York. “He was that smart guy you knew in college [who] was funny and saying the thing that you were thinking and wish[ing] you could say.”

  Stewart concurred.

  The show was a natural fit for him, he was enjoying himself despite the breakneck schedule of cranking out four shows each week, and the job clearly was not going to go away anytime soon. As a result, Jon appeared to, well, become more Jon. “I always liked him, but when he became Jon Stewart he seemed to become more content with who he was,” said Noam Dworman, who owned the Comedy Cellar where Stewart had cut his teeth in stand-up. “He seemed to be where he was and felt he should be, and it seemed to have a relaxing effect on his personality.”

  Even though he became more Jon on The Daily Show, Stewart said that just like his stand-up persona was a more exaggerated version of himself, the same applied to his TV host persona.

  “It’s pretty close, but also not close in the sense of I don’t live my life like it’s a half hour, like it’s a show, it’s a performance,” he said. “At home, I don’t go to commercial after breakfast. I’m not playing a character, it’s just a heightened performance.”

  He did admit that after years of starts and stops, The Daily Show was where he hit on all cylinders. “The only things that I am able to do, I am able to do here,” he said.

  For maybe the first time in his life, he was being true to himself.

  “I think people are responsible for themselves, for the most part,” he added. “I think you’re responsible to present yourself, to be as positive a person as you can be, whether it’s because you’re Jewish or black or Asian or whatever you are. I honestly think we’d be so much better off if that’s what people focus on. There’s really one rule: the golden rule. Focus on that, and it really doesn’t matter.”

  Lest some people think he was solely on the lookout for a news hook or story to turn into a joke, the daily headlines of that first year on the air were not all fair game for Stewart and the team. “All of the images coming out of Kosovo were so horrific, you think,… ‘There’s nothing funny about this,’” he said. “And then … ‘Fabio got hit in the face with a goose!’ … It was like receiving a gift from the gods.”

  * * *

  Part of the reason why Stewart seemed more settled was simply because in addition to his professional life becoming more established, the same thing was happening in his personal life. He and his girlfriend, Tracey, were now living together in a loft in downtown Manhattan, and they were engaged to be married.

  One of the things that won her heart from the beginning was when they played games together.

  He had proposed in a unique way: he asked Will Shortz, the crossword editor of the New York Times, for help. They had met previously when they were both guests on Late Night with Conan O’Brien and became friends. A few months later, Stewart asked Shortz if he could drop a few hints into an upcoming crossword puzzle since both he and Tracey loved to work on the puzzle each day.

  “It was two days before Valentine’s Day and Jon comes home and says, ‘I remembered to bring those crossword puzzles home,’” said Tracey. “As I start to fill it out, there are all these words in it that relate to us.”

  “There were [a few] little things in there that related to her,” he said.

  One of the hints was “1969 Miracle Met baseball player Art.” The answer, Shamsky, also referred to their dog named Shamsky, who Stewart referred to as his best friend. Shamsky was a rescued pit bull who Stewart claimed was agoraphobic and needed much coaxing to go outside.

  “They’re very misunderstood animals,” he said. “At the pound in New York, they’re pretty much the most common animal, I’m sorry to say. People think of them as vicious soldiers, but they’re actually quite sweet and playful. People get them for certain purposes that they don’t work out for and then they discard them. Shamsky unfortunately was not treated particularly well early in life, so I think she has some residual emotional damage. Although you could say that probably about most people you meet.”

  Another hint in the puzzle was “tool company,” which pertained to their cat named Stanley. “Then another clue was ‘Valentine’s Day Request,’ and it’s ‘Will you marry me?’” said Tracey. “[The next] clue was ‘Recipient of the Request.’ I look at it saying, ‘It almost looks like my name could fit in there.’”

  Stewart works diligently on one of his favorite pastimes—the New York Times daily crossword puzzle—in Wordplay, a documentary about the newspaper’s puzzle editor Will Shortz. (Courtesy REX USA/c.IFC Films/Everett)

  It did. They were married in 2000.

  He was so grateful for his newly happy, settled life that he finally buckled down under Tracey’s pressure and quit smoking cold turkey that same year. “I didn’t realize it at the time, but after you cut out smoking, drinking, and drugs, you feel much better,” he said.

  He was profoundly grateful for finding Tracey. “Let me put it this way, I know that I married up,” he said. “And I know how women felt about me before television. When I was a bachelor, I did fine, but usually it had to do with the fact that I was bartending or had a show.”

  As they prepared to start a family, the
y filed a motion with the court to change both of their names to Stewart; legally, Jon was still known as Leibowitz, and some speculated that he made the change in order to put one more step between him and his still estranged father, especially since he was eagerly looking forward to becoming a father himself.

  But they weren’t certain if that would come to pass. They tried several rounds of in vitro fertilization treatments and tried hard not to become discouraged and anxious.

  Stewart was also making his peace with religion, a concept that had dogged him since he was young. “Religion was one of the things I was hung up on in childhood that I sort of worked out,” he said. “It always baffled me. I tend to need logic in my life; I’m very poor with faith. While I do believe in God, I just don’t think he’s still looking out for us. I mean, if you think about it, he created the world in six days—five billion years ago! Don’t you think by now he’s moved on to another project? Maybe we’re just something he threw together for his third-grade science fair in the first place.”

  “I don’t have a problem with religion,” Stewart once explained to Larry King. “I think that religion provides a lot of people with comfort and solace, but you know, I think what people who aren’t that religious object to is [the belief] that the only way to find values is through religion.”

  And though others wondered about his mixed marriage—Tracey was raised Catholic—Stewart joked about the situation as usual. “My wife is Catholic, I’m Jewish, it’s very interesting: we’re raising the children to be sad.”

  * * *

  Happily, viewership of The Daily Show grew. Ratings increased steadily from the first night that Stewart held court. The critics weighed in:

  “I think the reason why people watch The Daily Show is because they have found, first of all, that it is extraordinarily funny,” said Devin Gordon of Newsweek. “They have found a place that is both extraordinarily funny and doesn’t insult their intelligence, which is a rare combination nowadays.”