Lisa Rogak - Angry Optimist

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.”

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.”