Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  “I think they’d both lose miserably,” said Musharraf.

  In the background of the usual breakneck schedule and performance in front of the camera, however, there was real trouble brewing. In late 2007, no one knew if The Daily Show would still be on the air in the near future, since the contract between the Writers Guild of America and TV producers and studios was set to expire. Since all Daily Show writers were now members of the union as of 2006, this meant that in case of a strike, there would be no show. Negotiations were ongoing, but chances for a resolution appeared to dim, and writers had already voted to strike if their demands were not met.

  The main sticking points revolved around digital media royalties—including the Internet and smartphone applications—and higher payments to writers for each DVD that sold with their work in it. At the time, writers earned four cents a DVD, which they wanted to be increased to eight cents.

  But like other daily news shows, even though it was a fake news show, The Daily Show still needed new content for each show. While some segments and features could be prepared in advance, much of the show was still cranked out up to the very last minute before taping that evening’s show.

  “We’ll be affected by a strike, as will be everybody else,” said Tony Fox, a spokesman for Comedy Central. “The two shows that are most impacted are The Daily Show and The Colbert Report because they air four nights a week.”

  Reruns were the only option, even though ratings plummeted whenever The Daily Show went into repeats. Another issue was that Stewart was a member of the Writers Guild as was Colbert. “They both write for their shows under the Writers Guild contract,” said Michael Winship, president of the Writers Guild’s East division. “Our position is that they could not do any of the work that they normally do as a Writers Guild member in terms of writing and performing material on the show.”

  As expected, talks broke down. More than twelve thousand TV, movie, and radio writers across the country went on strike on November 5, 2007, and The Daily Show went into repeats.

  Stewart took the strike as his first chance to take a break in years, and reveled in it, though it did take a little getting used to. Other late-night shows also went into reruns, including Late Night with Conan O’Brien, Late Show with David Letterman, and The Tonight Show with Jay Leno.

  However, pressure soon began to build from the networks that were losing money. Carson Daly was the first late-night talk-show host to return to the air, albeit reluctantly. “An ultimatum was put in front of me,” said Daly. “It was, ‘Put a new show on by December third or seventy-five people are fired. What’s your answer?’”

  Soon, other late-night shows began to cave. The next shows to return to work—without their writers—were Late Show with David Letterman and The Late Late Show with Craig Ferguson, both on CBS. Like Daly, both hosts explained that the entire nonwriting staff would be laid off if they continued to stay off the air. In late December, these shows and Late Night with Conan O’Brien announced they would return to the airwaves on January 2, 2008.

  Then, shortly before Christmas, Stewart announced that The Daily Show would return to Comedy Central on January 7th, presumably for similar reasons. He and Colbert offered up a joint statement: “We would like to return to work with our writers. If we cannot, we would like to express our ambivalence, but without our writers we are unable to express something as nuanced as ambivalence.”

  In acknowledgment of the striking writers, however, both Colbert and Stewart slightly altered the names of their shows: they became A Daily Show with Jon Stewart, while Colbert merely started pronouncing the t’s at the end of Colbert and Report.

  It was unclear how the show would turn out, given that the writers were such a vital part of the process. But after it aired, one critic weighed in, saying he thought a writer-less Daily Show was an improvement:

  “I found A Daily Show more compelling this evening,” said Thomas Tennant, who covers talk shows for About.com. “Stewart focused exclusively on the New Hampshire primaries. It was wonderfully insightful and biting, maybe a bit more biting than usual. I’m going to guess his writers pull him back from the edge from time to time—or at least balance him a bit.”

  The Show struggled along for almost six more weeks without the writers, with Stewart making lots of hits and misses and off-the-cuff improvisation. Correspondent John Oliver appeared in more segments than usual because as a British citizen, he was at risk of being deported if he went on strike. On February 12, the strike officially ended, the show returned the next day, and it didn’t take long for things to return to normal.

  * * *

  But Stewart’s version of normal for years had been a cycle of sheer exhaustion when it came to the show. He had hosted The Daily Show for ten years now. The cracks were beginning to show. And it was clear he was looking for a new challenge.

  But gripe as he might, Stewart still got fired up when he felt indignant about something, or saw someone in the middle getting stomped on.

  “If I wasn’t doing this, I’d be shouting at the TV,” he said. “There are mornings I walk in and view the news clips and it is the opposite of turning a light on. But then we go through … the day and it is cathartic and energizing.”

  Then, after a year when Ellen DeGeneres hosted, the Academy Awards decided to give him a second chance at hosting at the 2008 ceremony.

  Though his 2006 appearance had been middling, perhaps producers accepted that it wasn’t the easiest job in the world. As critic Gary Susman put it, “The job requires a difficult and rare set of skills: a host must entertain both the Hollywood big shots in the auditorium and regular folks at home.” He explained, “They can poke fun at the huge egos in the room, but can’t deflate them with too much snark, and they can’t be too inside baseball. Most of all, they have to think quickly on their feet, since there’s no telling what will happen during a live show broadcast to hundreds of millions around the world.”

  The second time was the charm for Stewart, in part due to the types of movies that were up for multiple nominations that year, including No Country for Old Men and There Will Be Blood. “His edginess fit the tone of the material,” said Susman.

  With the writers’ strike over and the Oscars behind him, Stewart settled into his third presidential campaign at The Daily Show. And what a gold mine of material it was, between the nomination of Sarah Palin as John McCain’s running mate and the Democratic primary showdown between the potential first woman and first African-American president, Hillary Clinton and Barack Obama. Despite his perceived burnout, it was clear that Stewart was energized by the comic opportunities presented during the yearlong Indecision 2008.

  Stewart and Colbert—along with correspondents from The Daily Show—joined forces on election night to present a live broadcast just as they had done in 2000 and 2004. In addition to the election of the first African-American president, another historic first occurred on the set of The Daily Show that very same night.

  The two fake news anchors reported real news for the very first time.

  The hour-long show was filled with correspondents reporting stories in front of green screens that made it seem like they were at the various campaign headquarters, but mixed in were factual updates on percentages and reports on states that had declared a clear winner. They were supposed to sign off at 11 P.M., because no one thought the election would be confirmed that night, but then one of the producers saw that CNN was going to call the election for Obama.

  So they kept the cameras rolling. Rob Kutner, a Daily Show writer, set the scene:

  “It’s a few minutes after eleven. The Colbert writers have occupied our writers’ lounge and are stinking drunk on Crystal Head Vodka,” he said. “We stall it just a little longer. The producer signals to Jon and Stephen at the desk, giving them the thumbs-up. Then, Jon made the announcement, for the first time ever, delivering a piece of real news.”

  “I would just like to say, if I may,” Stewart said, his voice catching slightly,
“that at eleven o’clock at night, Eastern Standard Time, the president of the United States is Barack Obama. We don’t normally do this live. We’re a fake news show.”

  Though Colbert whooped it up during the show when a state was announced for McCain and despondently groaned when one went for Obama, when it was all over, he actually felt a bit uncomfortable. “I’ve never had this feeling before,” he said. “Things actually went well on election night. I’m a little stunned. I don’t know what to do with my happiness. I’m still afraid someone’s going to take it away.”

  CHAPTER 11

  WITH THE ELECTION of the first African-American president, viewers and critics alike expected Stewart to go easy on Obama. And indeed, Stewart did run a number of lighthearted segments on the new president in the first year, including a piece called “Obama Kills a Fly,” about the moment when the president smacked a fly dead in the middle of an interview on CNBC.

  Critics who predicted Stewart would soften in the wake of a new Democratic president—and who missed the Stewart of the Bush era—were rightfully disappointed in what they viewed as a toothless new version of The Daily Show. They might have been on track with their accusations. However, Stewart pointed out a whole other set of challenges that he and the show’s producers faced after more than a decade at the helm.

  For one, the speed with which a news story hits and then vanishes had ramped up several times since 1999.

  And he publicly admitted that it was becoming more difficult to shake things up and make a story—and his style of approaching it—sound totally fresh and new. “I have a small bag of tricks, and try to deploy them in various permutations,” he said. “Then again, I also feel that limitations are one of the keys to creativity. If it came easy, maybe I wouldn’t have worked as hard.”

  At the same time, Stewart felt that the show had improved through the years. “I think it’s a better show now than it was ten years ago, we’re more consistent,” he said.

  With a surefire punching bag no longer occupying the White House, Stewart had to find different targets, which of course didn’t take him long. But he was mystified when some not only didn’t play along but fired back at him.

  For instance, while Stewart never made any effort to hide his dislike of CNN even years after his Crossfire appearance—“Oh, I’m sorry—are we on CNN right now? I thought this was the pre-show banter,” he said during an appearance on Larry King Live in October 2010—he continued to goad certain people for reasons that turned out to be surprising.

  For example, Stewart put CNN anchor Rick Sanchez in the Daily Show crosshairs so often that many thought it suspicious. After Stewart had poked fun at Sanchez—who is Cuban-American—for everything from his unfamiliarity with United States geography to volunteering to be Tasered for a news story, Sanchez finally reached the breaking point in a very public way. During an interview with radio host Pete Dominick, Sanchez finally let loose. First he pegged Stewart as being an “elite Northeast establishment liberal” who had no idea what it was like to grow up in a lower-middle-class household, and then he let the big guns loose.

  “I grew up not speaking English, dealing with real prejudice every day as a kid,” he said. “I watched my dad work in a factory, wash dishes, drive a truck, get spit on. I’ve been told that I can’t do certain things in life simply because I was a Hispanic.

  “Deep down, when [Stewart] looks at a guy like me, he sees a guy automatically who belongs in the second tier, and not the top tier,” said Sanchez. “I think Jon Stewart’s a bigot. I think he looks at the world through his mom, who was a schoolteacher, and his dad, who was a physicist or something like that. Great, I’m so happy that he grew up in a suburban middle-class New Jersey home with everything you could ever imagine.”

  Perhaps Sanchez was unaware that Dominick was friends with both Colbert and Stewart and worked on both shows as the comedian who would warm up the audience before the taping began. It’s also possible that if Sanchez had stopped with just criticizing Stewart, perhaps he’d still be working at CNN. Instead he continued to not only rail on Stewart but his own bosses at the network. “I’m telling you that everybody who runs CNN is a lot like Stewart, and a lot of people who run all the other networks are a lot like Stewart, and to imply that somehow they, the people in this country who are Jewish, are an oppressed minority? I can’t see somebody not getting a job somewhere because they’re Jewish.”

  The reaction was swift. CNN fired him the next day, but for his part, Stewart reached out to Sanchez, whom he said had misunderstood why Stewart had latched on to him. According to Sanchez, Stewart told him, “I made fun of you because you’re the one I liked.”

  In time, Sanchez’s view of the comedian grew more nuanced. “I think Jon Stewart is misunderstood by a lot of people, and I say that as someone who misunderstood him myself,” he said. “There isn’t a ‘real’ Jon Stewart and another hiding behind comedy. It’s … the same person. He’s an equal-opportunity comedian [with] a simple, unified message and focus: he is opposed to extremes.”

  The reason why Stewart pursued Sanchez as a target may well have been this: the Sanchez exchange occurred just eighteen months into the Obama administration, and while Stewart had gone easy on the president in the first stretch of his administration, it was clear that he was becoming disillusioned with the president’s evolving record. And yet, he didn’t want to encourage Obama’s naysayers on the right—and even worse, an increasingly vocal faction within the Democratic Party—and so in targeting Sanchez it was as if he had admitted he had stooped to shooting fish in a barrel: it was an easy cheap shot at a TV reporter who Stewart had viewed as selling out.

  In essence, Jon Stewart had become the accursed establishment, the same thing he had accused CNN of becoming: the “straight down the middle” cable news network.

  Or as one critic put it, “Another night, another Daily Show about Fox News,” wrote Tom Junod in Esquire. “The problem is that Democrats, with their perpetual disarray, are not as funny as Republicans, with their reality-bending unity, and that Stewart is left to nurse what is probably the most potent comedy killer of all: disappointment.”

  “You can see the strain in his interviews,” said a former Daily Show writer. “It used to be, ‘Hey, we’re a comedy show.’ Now it’s, ‘What we do is so hard.’ And it is hard. One of the reasons I finally left is that we were running out of targets. I was like, ‘Do we really want to make fun of Fox & Friends again? Really?’”

  Eighteen months into Obama’s first term as president, though, the bloom was definitely off the rose as far as Stewart was concerned. “Obama ran as a visionary and leads as a legislator, which has been the most disappointing thing about him,” he said. “People were open to major changes, and they didn’t get it. I mean, he was pretty clear about some shit: ‘We’re not gonna sacrifice values for safety. I’m closing Guantanamo.’ [But] he’s more than willing to sacrifice someone to the voraciousness of the news cycle than to any sense of what his narrative is.”

  Stewart even went on The O’Reilly Factor on Fox News of all places to express his disappointment, though it wasn’t the first time he’d appeared there; the two have frequently gone on each other’s show through the years. “I thought we were in such a place we needed a more drastic reconstruction, perhaps, a destruction of the powers that be. I thought this may be a chance to do that. I have been saddened to see that someone who ran on the idea that you can’t expect to get different results with the same people in the same system has kept in place so much of the same system and the same people. There was a sense that, ‘Jesus will walk on water,’ and now we’re just looking at it like, ‘Oh, look at that, he’s just treading water.’”

  Despite his disappointment and outward criticism, on October 27, 2010, Stewart welcomed President Obama to The Daily Show as the first sitting president to come onto the show. The appearance was supposed to be a midterm check-in as to Obama’s progress since he’d been elected, and the two spent the full half-
hour gently chiding and joking with each other, although the exchange was as far from a typical Stewart interview as you could get, with Obama speaking at length without interruption from Stewart and the host failing to mug for the cameras as he typically did during his opening segment. After the show aired, Stewart would complain that despite prodding from him, the president didn’t unleash his humorous side.

  President Barack Obama appears on The Daily Show on October 27, 2010. (Courtesy REX USA/Rex)

  Indeed, correspondent Wyatt Cenac said that Obama was a “terrible improviser and Stewart sort of likes to improvise these jokes.”

  In the end, perhaps the most poignant aspect to come out of the segment was that both concurred that changing America was harder than it initially looked when Obama first came to office:

  “‘Yes we can,’ given certain conditions,” said Stewart.

  “‘Yes we can,’ but it’s not gonna happen overnight,” the president replied.

  * * *

  To temper the everyday sameness of producing a grueling schedule of a show four nights a week, Stewart continued to pull back a bit and turn to other projects, all radically different from one another.

  First, in early 2010 he announced that he had purchased the film options to the life story of Maziar Bahari, an Iranian-Canadian journalist and filmmaker who was arrested by the Iranian government on suspicion of being a spy, a suspicion that had originated in a Daily Show segment from 2009 where correspondent Jason Jones—dressed as a spy—interviewed him. Once Bahari returned to Iran, he was held at the notorious Evin Prison—“every Iranian’s nightmare,” as another detained journalist called it—where he was tortured and interrogated for 118 days before his release. He returned to London and wrote a book about his time in prison and also incorporated his family history into the story. Then They Came for Me was published in 2011 and hit the New York Times best-seller list; Bahari also appeared on the June 6, 2011, episode of The Daily Show, in part to promote the book. Stewart started to write the screenplay and also planned to produce and direct the film.