Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  Even though the book’s publication was a personal coup not only for Stewart but for the show he had built and nurtured, perhaps the most personal and heartfelt accomplishment came when he appeared on the CNN show Crossfire on October 15, 2004, though it was at times painful to watch his exchange with host Tucker Carlson and cohost Paul Begala.

  In the years since 1999 and Stewart’s debut on The Daily Show, whenever he appeared on other talk shows, he did it out of a sense of duty and obligation. Even though it was clear he’d rather be somewhere else, he was always a good guest and never ruffled any feathers. So Carlson and Begala expected nothing different despite the fact that Stewart occasionally raked the show across the coals on The Daily Show.

  What had escaped everybody’s notice was that Stewart planned to do the same on their show.

  * * *

  When Stewart agreed to appear on the show, coming on the heels of the publication of his new book, everyone from the producers on down thought it would be a nice easy visit. Some lighthearted jabs would undoubtedly ensue, but at the end of the fourteen-minute segment, everyone would grin, shake hands, exchange a few gracious words for the sake of the audience, and then go their merry way.

  But that’s not what happened at all. The first person to have a clue was Begala, who met with Stewart in the green room before the show for some chitchat. He thought that Stewart’s demeanor seemed off in some regard.

  He later realized that Stewart had planned to go on the offensive from the very beginning, and in fact it was the reason why he agreed to appear on the show in the first place. “I thought he was going to push his book that had just come out, but he wanted to be more serious,” Begala remembered.

  From the beginning, Stewart was out of character and unusually humorless; he didn’t smile once when speaking with Carlson. During his diatribe, he pushed his overall philosophy that claimed politicians and media are bad, and attacked both sides while saying that Crossfire was “hurting America.”

  The main sticking point of the show was when Carlson accused Stewart of playing softball with Kerry on The Daily Show, the same sin Stewart was hurling at Carlson on Crossfire. “You have him on your show and you sniff his throne and you are accusing us of partisan hackery?” asked an incredulous Carlson.

  “Absolutely,” Stewart replied.

  Carlson: “You have got to be kidding me!”

  “You are on CNN,” said Stewart, “the show that leads into me is puppets making crank phone calls. What is wrong with you?”

  After several more volleys exchanged between Stewart and the cohosts, Carlson whined, “I thought you were going to be funny.”

  “No,” said Stewart, “I’m not going to be your monkey.”

  Later on, Carlson reflected on the segment. “I knew he had these kinds of pretensions about being a political thinker, but I didn’t take him seriously and I don’t take him seriously now,” he said. “I was shocked by the preachiness of it, and was kind of embarrassed for him.”

  Whatever Carlson thought, the exchange attracted the attention of viewers, critics, and CNN.

  “When Stewart snapped at Tucker that way, it was one of those flash points in television,” said David Hinckley. “We’ve got this era now when reality TV means anything but reality, so you get a moment like that on Crossfire and think, whoa. It’s like you’ve been slapped in the face. This was real.”

  However, other critics weren’t buying Stewart’s defense. “The puppet thing is just his way of deflecting,” said Rachel Sklar, lawyer and former editor at The Huffington Post. “The fact is that The Daily Show and The Colbert Report are more than just shows that go on at eleven o’clock at night to a specific number of viewers. They’re picked up the next day on YouTube. They’re picked up by blogs. And they’re picked up as … genuine news stories on the Associated Press.”

  Sklar wasn’t done. “He’s a good interviewer and he knows his stuff. And when people are on the show, they have genuine discussions, and sometimes they break news.”

  Looking back, it’s not like the Crossfire host hadn’t been warned. In the weeks leading up to his Crossfire appearance, Stewart had appeared on several shows—including National Public Radio’s Fresh Air—touting the same ideas as a warm-up.

  “Political parties are basically dedicated to figuring out how to game the system … and are actively exploiting that loophole,” he told host Terry Gross.

  And his criticisms had existed years before, when Stewart characterized the tone of his show just a week into his tenure back in 1999: “The Daily Show seems to be a nice sort of pin in the balloon,” he said.

  Crossfire had expected him to be the typical convivial, slightly smirking talk-show host always ready with a quick retort or arch comment or observation to poke fun at someone in the news. But he’d shown up with a more serious agenda. In any case, while the highly charged exchange brought out the critics in some corners, it only served to cement Stewart as a hero in others.

  Stewart had only two regrets about his appearance. “The reason everyone on Crossfire freaked out is that I didn’t play the role I was supposed to play. I was expected to do some funny jokes, then go have a beer with everyone.” He also noted that some critics thought he had a personal beef with Carlson because of the caustic back and forth between them, but Stewart maintains he was specifically criticizing the tone and format of the show and not the hosts.

  What happened next surprised even Stewart: Crossfire was canceled shortly after his appearance. Jonathan Klein, the recently hired president of CNN, succumbed to pressure from advertisers—which was nonexistent before Stewart went on the show, though the show had also experienced lower ratings over the previous year—and announced that he’d cancel the show. “I guess I come down more firmly in the Jon Stewart camp,” he said. “I doubt that when the president sits down with his advisers they scream at him to bring him up to date on all of the issues. I don’t know why we don’t treat the audience with the same respect.”

  In the wake of Crossfire, however, some other members of the media were beginning to publicly take issue with Stewart’s constant finger-pointing and his harangues directed toward them and their supposed lack of integrity.

  “The Jon Stewart backlash should start right about now,” said Wonkette founder Ana Marie Cox after news of the cancellation hit. “Stewart has pretty much painted a target on his chest with his Crossfire appearance. To say his is just a comedy show is a cop-out in a way. He’s gotten so much power. So many people look to him that you can’t really be the kid in the back throwing spitballs.”

  “Jon gets to decide the rules governing his own activism and the causes he supports and how often he does it,” said Brian Williams, anchor of the NBC Nightly News. “And his audience gets to decide if they like the serious Jon as much as they do the satirical Jon.

  “He has chronicled the death of shame in politics and journalism, and many of us on this side of the journalism tracks often wish we were on Jon’s side,” Williams added. “I envy his platform to shout from the mountaintop. He’s a necessary branch of government.”

  Veteran newsman Ted Koppel also stepped into the fray. “Jon feels [journalists] should be more opinionated, not less, and he feels I have a responsibility to get in there and tell the public, ‘Look, this guy is lying’—although maybe not quite that blatantly,” he said. “I disagree with that only in part. In a live interview you can say, ‘That doesn’t sound right,’ but you don’t automatically have all the facts at your disposal. Jon is really profoundly concerned and angry about real issues, but a satirist gets to poke and prod and make fun of other people, and when you say, ‘What about you, dummy?’ he says, ‘I’m just a satirist.’”

  For Stewart’s part, at this stage in his life, all the criticism just tended to roll off his back. “I really feel like I have gotten to this weird place where rejection is a good kind of pain,” he said. “Like you get a shot to the ribs sometimes and you go, eh, I’m alive, you know what I mean? Like
you get to a certain baseline where you feel confident in your ability to do that tiny little thing that you do. And the other stuff that you’ve been allowed to do is sort of gravy, and if it doesn’t work out, that’s really all right.”

  Some serious journalists continued to cheer him on. “Jon Stewart doesn’t claim to be a journalist, and when he says he’s not we should believe it,” said Robert Thompson, director of the Bleier Center for Television and Popular Culture at Syracuse University. “His interviews are in the tradition of Johnny Carson, where he’s polite, at times deferential, and behaves in the interviews like a well-brought-up young man.” In Thompson’s view, that’s where they part company and Stewart morphs into something totally unique. “When all the news guys were walking on eggshells [during the Iraq war], Jon was hammering those questions about WMDs. That’s the kind of thing CNN and CBS should have been doing.”

  Even the formidable Bill Moyers, a veteran newsman who served as press secretary to President Lyndon B. Johnson before launching a decades-long career in political journalism in network news and public broadcasting, weighed in with effusive praise that was unusual for him. “When I report the news on this broadcast, people say I’m making it up, but when Stewart makes it up, they say he’s telling the truth,” said Moyers. “When future historians come to write the political story of our times, they will first have to review hundreds of hours of a cable television program called The Daily Show. You simply can’t understand American politics in the new millennium without The Daily Show.”

  * * *

  As the presidential campaign of 2004 ran on, the lines between real and fake news continued to blur in Stewart’s world, as well as on the show.

  First, John Edwards went on the show to announce his presidential candidacy. Stewart quipped, “We are a fake show, so you might have to do this again somewhere.”

  Then Stewart announced that he planned to vote for John Kerry. While it wasn’t a total surprise given that the most frequent targets on the show happen to be Republicans, the fact that he aired it in public made it appear to be an endorsement coming from not only him but the show, which was an unusual move.

  “There’s no question that at a certain point that we were leaning toward a certain election result,” he said. “That doesn’t mean we thought one side was pure and the other evil. If you watched this show and didn’t know I was voting for Kerry you’re clearly not paying attention to the show. But if you think that by announcing it that I’ve lost my credibility as a comedian, I just didn’t think we had any credibility to lose.”

  Even though he continually maintained that he had no power, it was crystal clear that he wished to have an impact on the business-as-usual politics and the media. However, to his great dismay, both just dug in their heels and became more entrenched, sensationalistic, and polarized. On the show the night before the 2004 presidential election, he had this to say:

  “Tomorrow when you go to the polls, make my life difficult. Make the next four years really hard, so that every morning all we can do is come in and go, ‘Madonna is doing some kabbalah thing, you wanna do that?’ I’d like that. I’m tired.”

  Perhaps as the result of the combination of all of these things, an interesting thing happened: Stewart was no longer the funniest guy on the show, the clown. He morphed from the zany one on the show and turned into the calm one, the occasionally austere older anchor while all around him the—mostly younger—correspondents acted out of turn, went for the cheap joke or visual or pratfall. Though he may deny he is anything but a comedian until the day he dies, Stewart had turned into an authority figure along the way.

  The Daily Show had made a star out of its host, and now the same thing was starting to happen with its correspondents.

  After the success of his costarring role as Evan Baxter in the 2003 Jim Carrey movie Bruce Almighty, Steve Carell was already getting more movie and TV offers from Hollywood. He left The Daily Show in the spring of 2004 to begin work on the American version of The Office, based on a popular BBC series, and The 40-Year-Old Virgin, a movie that would be released in 2005. After Carell’s departure, Colbert became the next in line, but it was clear that Stewart wasn’t going anywhere soon.

  However, in addition to his hosting and producing duties, Stewart was actively searching for new projects for his Busboy Productions to take on. He had recently signed a deal with Comedy Central to pursue new projects, and they didn’t have to look far.

  And then just like that, it was Colbert’s turn.

  “At that time, he was a total rock star among correspondents,” said Bob Wiltfong. “When any of his stories ran, there was a huge reaction from the audience. The feeling among the rest of us was, why is this guy still on the show?”

  Besides, Colbert was getting restless. “I couldn’t imagine how much longer I could do it,” he said. “I still liked it, and I didn’t want to not like it.”

  “If your name’s not Jon Stewart, there’s only so many places you can go on The Daily Show,” said executive producer Ben Karlin. “Steve Carell and Steve Colbert were the first two we identified as giant talents with breakout potential, but we didn’t have the mechanism in place when Steve Carell started getting offers, so he left. With Stephen, we didn’t want to have him go off and become a huge star without working with him.”

  “He’d been there a long time,” added Karlin. “He was never going to be the host, it was Jon’s show. But we didn’t want to lose him, so we tried to figure out what else someone like Stephen could do.”

  They remembered those fake promos for the fake Colbert Report that had aired several times on The Daily Show. One day in the fall of 2003, when working on scripts for The Daily Show, the producers and writers had discovered that one segment was running a bit short.

  Why not run a fake ad for a fake show starring a fake news correspondent?

  They ran it by Colbert, and it sounded good to him. The writers came up with a promo for the imaginary Colbert Report despite the fact that the show didn’t exist.

  “I tried to ape whoever was the loudest and rightest in prime-time cable news,” he said. They produced four of these promos, which ran through 2003 and 2004, and thought nothing more of it.

  Executives at Comedy Central were looking to extend The Daily Show franchise, as were Stewart and Karlin for Busboy Productions. Perhaps the fake promos had planted the seed, but building a show around Colbert’s character seemed doable.

  The O’Reilly Factor with Stephen Colbert was how they pitched it.

  Once they started to flesh out the show, Colbert said, “But I can’t be an asshole.”

  “You’re not an asshole,” said Stewart. “You’re an idiot. There’s a difference.”

  Colbert agreed. “The audience wouldn’t forgive Jon for saying things most comedians would want to say,” he said. “But we can say almost anything, because it’s coming out of the mouth of this character.”

  “The challenge of these things is how to evolve and keep it fresh and keep people from being bored with your voice,” said Stewart. “We were lucky to have the guy as long as we had him. In fact, one year we kept him because we hid his keys.”

  The deal was made and announced in the spring of 2005: Stephen Colbert would host his own show starting in the fall. And Stewart’s Busboy Productions would serve as executive producers.

  The first episode of The Colbert Report went on the air on October 17, 2005.

  “It became so clear so quickly that it was going to work that it was kind of astounding,” said Comedy Central president Doug Herzog. “When the show debuted, I remember thinking that it had been birthed fully baked. That’s so rare. I don’t know if I’ve ever seen it before. The whole thing fits him like a glove. It’s really a virtuoso performance.”

  “The Colbert Report depends on Stephen’s ability to process information as this other person,” said Stewart. “Watch Colbert and it’s like the first time you use broadband: ‘How the fuck did that happen?’ He’s rendering in
real time. He’s basically doing his show in a second language.”

  After only eight shows, Comedy Central renewed The Colbert Report for an entire year.

  * * *

  For all of the critiquing and finger-pointing he was doing at the media and politicians, it turned out that in his private life—which he still heavily guarded—Stewart was turning into one big softy.

  “When I look at Nathan, I think, I could kill someone for him. In fact, I could do it almost every day,” he admitted.

  “I am a neutered cat, which is a very contented and warm feeling.”

  CHAPTER 10

  IN THE SPRING of 2006, Stewart got his chance to perform in the ultimate stand-up venue:

  The Oscars.

  It was a controversial choice. For the most part, the celebrities chosen to host the annual awards ceremony are reliable middle-of-the-road stars, like Billy Crystal and Johnny Carson. In other words, stars who were considered safe, not automatically detested by a good chunk of the American public, and who wouldn’t run off the rails in front of an audience of up to 55 million people—the audience for the 1998 show when the movie Titanic attracted a record audience. Chris Rock had hosted the 2005 show, and viewership for the night had dropped 3 percent from the year before, going from 43.5 million viewers in 2004 to 42.1 million in 2005.

  The Oscar producers also didn’t like the potential for political humor to disrupt the flow of the night—or for a host to unleash a few barbed zingers—and so the selection of Stewart was definitely a risk because they wanted to draw in more young viewers.

  Stewart and his wife, Tracey McShane, attending the Governor’s Ball at the Academy Awards on March 5, 2006. (Courtesy BEImages/Alex J. Berliner)

  “You have to be humorous and able to prick the pomposity of it without coming across as mean-spirited or nasty,” said Damien Bona, author of Inside Oscar.

  “It’s a lot of pressure; I’m very glad I’m not getting ready right now,” Chris Rock said in advance of the 2006 broadcast. “This time last year, I was losing my mind.”