Lisa Rogak - Angry Optimist

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A
Bestseller Since his arrival at
in 1999, Jon Stewart has become one of the major players in comedy as well as one of the most significant liberal voices in the media. In
, biographer Lisa Rogak charts his unlikely rise to stardom. She follows him from his early days growing up in New Jersey, through his years as a struggling stand-up comic in New York, and on to the short-lived but acclaimed
. And she charts his humbling string of near-misses—passed over as a replacement for shows hosted by Conan O’Brien, Tom Snyder, and even the fictional Larry Sanders—before landing on a half-hour comedy show that at the time was still finding its footing amidst roiling internal drama.
Once there, Stewart transformed
into one of the most influential news programs on television today. Drawing on interviews with current and former colleagues, Rogak reveals how things work—and sometimes don’t work—behind the scenes at
led by Jon Stewart, a comedian who has come to wield incredible power in American politics.

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* * *

Not only were politicians and presidential candidates clamoring to appear on The Daily Show, leaders of other countries wanted to get their shot with Stewart as well.

In September of 2006, Pervez Musharraf, the president of Pakistan, was booked on the show to promote his new book In the Line of Fire .

“Where’s Osama bin Laden?” Stewart asked him suddenly.

“I don’t know,” replied Musharraf. “You know where he is? You lead on, we’ll follow you.”

In a variation on the theme of his interview with Kerry, Stewart took a more lighthearted approach to his talk with Musharraf. After serving up tea and Twinkies, Stewart put the Pakistani president on the “Seat of Heat,” a recently introduced segment where the lights go down low while a series of red lights flashed on and off before he asks his guest one last question.

“George W. Bush and Osama bin Laden—be truthful—who would win a popular vote in Pakistan?” asked Stewart.

“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.

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