Angry Optimist

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.

“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.”

For his part, Stewart tried to distract himself from the task at hand. “Free time is death to the anxious, and thank goodness I don’t have any of it right now,” he said.

Stewart fully realized the precarious situation he was in—as well as acknowledging the real honor—and so for the most part he played it safe. The most political joke he told was this: “I do have some sad news to report: Björk couldn’t be here tonight. She was trying on her Oscar dress and Dick Cheney shot her.”

The rest of the time, he stuck to the tried-and-true with quips like, “We’ve got movies about racism, prejudice, censorship, murders. This is why we go to movies, for an escape,” and “The Oscars is really I guess the one night of the year when you can see all your favorite stars without having to donate any money to the Democratic Party. And it’s exciting for the stars as well because it’s the first time many of you have ever voted for a winner.”

The critics were not kind. “It’s hard to believe that professional entertainers could have put together a show less entertaining than this year’s Oscars, hosted with a smug humorlessness by comic Jon Stewart, a sad and pale shadow of great hosts gone by,” said Tom Shales of the Washington Post.

The New York Times hurled the biggest insult anyone could at Stewart: “He wasn’t as funny as he usually is,” wrote the critic.

“He’s such a great performer and that’s what makes it so hard,” said his mentor, Caroline Hirsch. “That audience is an audience of performers, and it’s almost like they’re saying, prove it to me, make me laugh. And that’s hard to do. Doing the Oscars is a really hard gig.”

To be sure, the show didn’t get off to a great start. “The show began with a montage of previous hosts turning down the thankless gig, making Stewart seem like the last guy standing after a game of musical chairs,” wrote Gary Susman, a critic with Moviefone.com.

In his own postmortem, Stewart didn’t beat himself up over the reviews. “When you’re dealing with a group where eighty percent are walking home empty-handed, you want to make sure that when that night is over they don’t feel like they have just wasted twelve hours,” he said. “I actually didn’t think it was such a bad job.”

However, in the wake of the Oscars, some critics—and viewers—began to think that now that he was in his eighth year of meeting the grinding demands of The Daily Show, maybe it was time for Stewart to take a break, maybe look to something different and let someone else take the reins for a while.

Executive producer Ben Karlin—in many eyes, Stewart’s anchor since day one—had been essentially running both shows since he assumed responsibility for the launch of The Colbert Report in 2005, and he had finally confessed he was wrung out from the schedule in 2006.

Plus, maybe the bigger sin was that after almost eight years of full-tilt production, it was simply a lot harder to come up with something funny. “You definitely get more intellectual about comedy,” Karlin admitted. “The laugh impulse has been deadened.”

Part of the problem was that The Daily Show was tried-and-true, while The Colbert Report was fresh and new, and though it was still finding its legs, the format and tone were so radically different from Stewart’s show that viewers increasingly opted to watch Colbert over Stewart.

One critic hit the nail on the head when he suggested the reason why The Daily Show was starting to feel like a chore. “The Daily Show is like a really good marriage: solid, dependable, and deeply satisfying, but the mystery, wonder, and freshness are gone. I still think The Daily Show suffers from the absence of a Colbert or Carell. The Colbert Report, on the other hand, is like the giddy infatuation of new love. Anything seems possible. The sky’s the limit.”

And so while viewers who were inclined to watch both shows back-to-back may have had Stewart’s show on as background, as soon as 11:30 hit, they turned up the volume on the TV and really focused on Colbert. At that point, you never knew what he would do or say. The novelty of watching him introduce a guest and then run around the studio waving and bowing and accepting the audience’s raucous applause was still fresh. Plus, the caliber of guests he was able to attract was already leagues beyond Stewart’s: one night, Stewart interviewed Ben Stiller, while Colbert spoke with Peter Frampton and Henry Kissinger, both interviewed in his inimitable razor-sharp style.

“The jokes in each episode of The Daily Show now follow a rigid pattern,” wrote another critic. “Either they show a clip of a politician saying something stupid, followed by a cut to Stewart’s shocked/bemused expression, or Stewart has to deal with a fake news ‘correspondent’ who doesn’t quite understand what is going on in the world. While The Colbert Report could be weird to the point of incomprehensibility, it was at least surprising.”

Perhaps it was inevitable, but another problem with the Show was that Stewart’s particular brand of satirical fake news had begun to spread as traditional news programs started to ride Stewart’s coattails and began to adopt some of The Daily Show’s characteristics. Keith Olbermann, who helped launch the MSNBC show Countdown in 2003, introduced a couple of segments in 2005 and 2006—respectively Worst Person in the World and Special Comments—which could have been lifted directly from a Stewart monologue, often poking fun and criticizing George W. Bush and Fox News. Soon, other news hosts and programs followed suit in both national and smaller markets.

Stewart was also picking some odd fights, and in a very public way. When he hosted financial expert Jim Cramer, host of CNBC’s Mad Money, on the show in the spring of 2009, both Comedy Central and CNBC played it up for the week preceding as being the fight of the century, or at least a good rollicking repeat of Stewart’s Crossfire appearance.

Essentially, Stewart accused Cramer and his network of complicity for misleading his viewers with inaccurate and over-the-top financial advice in the period before the economy began to tank in 2008.

“I understand that you want to make finance entertaining, but it’s not a fucking game,” said Stewart. “We’re both snake-oil salesmen to a certain extent. But we do label the show as snake oil here. Isn’t there a problem selling snake oil as vitamin tonic and saying that it cures impetigo?”

Instead of fighting back like Tucker Carlson had done, however, Cramer meekly nodded and agreed with Stewart’s barbs for the most part. “I try really hard to make as many good calls as I can,” he said. “I, too, like you, want to have a successful show. Should we have been constantly pointing out the mistakes that were made? Absolutely. I truly wish we had done more.”

While some critics—and many financial advisers—applauded Stewart for taking on Cramer, others had had enough of his good-guy tactics.

Regular fans were beginning to turn away. “Typically, I am a fan of The Daily Show, but I honestly believe Jon Stewart has taken a low blow with this verbal scuffle with Jim Cramer,” said one viewer. “Not only is it mean-spirited and unnecessary, but it’s not funny. And just as Cramer is paid to excite us about Wall Street, Stewart is paid to make us laugh. I wish he’d get back to work.”

Was Stewart getting tired? Was he getting so restless that he could no longer hide it? After all, it had been a decade since he had taken over from Craig Kilborn, who himself succumbed to complacency and predictability in the rigors of creating a new show from scratch four nights a week and had left The Late Late Show with Craig Kilborn just five years after ditching The Daily Show.

Though Stewart has never outwardly admitted if he’s been blocked—whether by a lack of creativity or by sheer exhaustion—he has said that the pressure of an insane deadline never fails to spur him on to finding just the right joke or new angle for a sketch.

Or maybe it was just the simple fact that he was so happy and content in his personal life that the pressure and crushing deadlines that he had to endure at the studio on a daily basis were getting harder to take. “When I’m in, I’m in,” he said.

He also had just become a father for the second time. Daughter Maggie Rose Stewart was born in February 2006, and though he had adjusted nicely to life with his son, he was a bit nervous about the prospect of dealing with a daughter.

“I don’t know that much about women,” he said. “A boy child, I feel like I’ll know how to deal with it if he has a problem. I’ll just be able to say to him, ‘Well, repress it,’ and hopefully he’ll swallow that, as I have. And then you figure you have thirty years before it comes out over dinner where somebody spills the gravy and then you’re like ‘I hate you!’

“But a girl, she’s going to want me to have tea with her and her panda. What am I going to do with that?”

To accommodate his growing family, in 2005 he and Tracey had bought a six-thousand-square-foot Tribeca duplex penthouse loft for almost $6 million through a real estate trust named the Shamsky Monkey Trust after his cat and dog. A few years later in 2008, Forbes would estimate his annual income at $14 million.

The loft quickly became his retreat from the world, and after the postmortem on the show wraps, he rushes out the door and heads downtown for home to see his wife and kids and animals. Most surprisingly, he turns into the polar opposite of his TV persona once he closes the door behind him. “He never talks about politics or world events,” Tracey said.

His sense of humor also morphs into something entirely different. “He’s silly, but it’s not like I live with a jokester,” she added. “He’s not annoying and not always on. Jon is not even that smart at home. He’s really all about his family.”

His dogs now included a new third addition, a three-legged pooch named Little Dipper. “The whole family can fit in one bed with three dogs placed strategically,” he said. “And the dogs are all pretty good about going under the covers and curling up. One nice thing is that it does generate a lot of heat. It’s like having one of those brick ovens that they make pizza in. The three of them get in there and it fires us up to thermonuclear levels.”

Both Tracey and Jon were totally enthralled with being parents. “We both think the same things are funny and we both value the same things. So parenting for us is very easy as far as our relationship goes because we always see eye to eye [with] the kids,” said Tracey. “Nate is very gentle, sweet, sensitive, emotional, and kind and loves Star Wars and football, while Maggie is hilarious and irreverent, like her dad in girl form…. I always say that she’s me on the inside and Jon on the outside. And Nate is Jon on the outside and me on the inside.”

Unlike many celebrities and people in the public eye, Stewart purposely avoids the spotlight. “I’m not a particularly social animal,” he said. Indeed, he rarely attends black-tie events in Manhattan and once even passed up the chance to pick up an Emmy at the annual awards ceremony. “You go to a party, those people don’t need you to open shit or help them get their pants on. So they’re not nearly so nice to you.”

One of the Stewart family’s favorite things to do is to watch the Food Network, particularly Restaurant Impossible, Cupcake Wars, Chopped, and Iron Chef. Though Tracey doesn’t like to cook, the food shows have motivated both Nate and Maggie to learn to cook.

While Stewart’s outlook and priorities were changing and he seemed understandably exhausted, he may have become less funny than he used to be for another reason: when he first started hosting the Show back in 1999, Stewart still expected that his efforts would bring about some kind of change in the world, particularly the divisive, bitter world of American politics. Maybe it was a bit unrealistic, but he had held out hope that he could make a difference. While he still felt that way, it had become clear he had to shift gears and take real action in order to put his beliefs to the test.

So on December 16, 2010, Stewart devoted the entire Daily Show to the fact that thousands of September 11 first responders were suffering from some serious health problems. Even though Congress had crafted a bill that would give firefighters, policemen and -women, and EMTs a wide range of benefits to help them deal with it, a Republican filibuster late in the session—and before their lengthy vacation—stalled the bill, making it unlikely to pass. He also predictably chided the news media for not calling attention to the issue.

Stewart and his producers put their heads together and handpicked a roundtable of first responders to appear on a panel to tell their stories. A few days later, Congress ferried the bill through a vote and passed it. The local firemen were so thrilled that they threw a birthday party for Stewart’s daughter at the firehouse—complete with a fire truck–shaped birthday cake—and Robert J. Thompson, a professor at Syracuse University, instantly vaulted him to having the same status and influence as both Walter Cronkite and Edward R. Murrow, veteran newsmen who used their influence to turn around, respectively, a war and a government witch hunt.

Even though Stewart emphatically maintained time and again that he was not a journalist, a 2007 Pew survey showed that Americans believed Stewart to be on a par with Dan Rather and Tom Brokaw as the most widely admired journalists in the United States. Indeed, upon Cronkite’s death in 2009, Time magazine conducted a poll to ask readers their suggestions for his replacement as “most trusted man in America.” Stewart won with 44 percent of the vote, but predictably downplayed the results.

Despite the feeling of satisfaction Stewart derived from these accomplishments, it was just getting too difficult to bring about the kind of significant change that he hoped for. And there weren’t enough Daily Show episodes in the course of a year to change everything that he felt needed correcting on the political front.

Some missteps were beginning to appear along the way. On a 2009 Daily Show, out of nowhere Stewart told the audience he believed that President Harry Truman should have been considered a war criminal when he dropped atomic bombs on Hiroshima and Nagasaki. Overnight, widespread outrage predictably ensued from all political and social fronts, and Stewart came out with a public apology on the show a couple of days later:

“Right after saying it, I thought to myself: that was dumb,” he admitted. “And it was dumb. Stupid, in fact. So I shouldn’t have said that, and I say right now, no, I don’t believe that to be the case.”

Stewart won kudos from some unexpected fronts, with many conservatives saying he was right the first time. “I was a bit surprised, albeit pleasantly, to see Jon Stewart nail Harry Truman as a war criminal,” opined conservative critic Justin Raimondo, suggesting that it was Comedy Central executives who forced Stewart’s apology, and not his fans. After all, the audience that day actually cheered at Stewart’s announcement during the show.

“Rule number one in this game is that everybody must play their assigned role,” Raimondo continued, “you’ve always got to be ‘in character.’ If you’re on the left, you can take on George W. Bush, murderer of hundreds of thousands of Iraqis—but not Harry Truman, killer of even larger numbers of innocent Japanese civilians.”

Karlin also attempted a feeble save on account of his boss. “Oftentimes, people who say satiric or unpleasant things are labeled as curmudgeons,” he said. “Jon has a very rare gift for being able to deliver material that has bite, but not in a mean or nasty way.”

But not everyone agreed, including a fellow comedian who had good reason to be eternally grateful to Stewart for providing his springboard to stardom. “It’s one thing poking fun at people who deserve it,” said Steve Carell. “But there was [always] that flip side of shooting fish in a barrel. It’s just cruel.”

And even one of his oldest friends, Anthony Weiner, turned on him. “I think that [cynicism] exists because of Jon’s show,” he said. “I think it becomes a feedback loop that’s corrosive. Congressmen do dumb things, then they’re highlighted for doing dumb things, and people watch it and say that congressmen do dumb things, and so then when another congressman does a dumb thing, [Stewart says], ‘Well, my audience wants to watch a congressman do a dumb thing.’ So when the audience laughs at the congressman doing a dumb thing, Jon says, ‘Hey, I got a great scam here, lemme go find another congressman doing a dumb thing.’”

It almost looked like Stewart was starting to realize the futility of his efforts to change politics and its media, where he was tempted to just say “fuck it” and succumb to his hermitlike tendencies. Especially when dealing with people who should know better, like the hosts of national talk shows.

Stewart launched into a diatribe on Larry King Live about the totally artificial front that politicians present to the public, and that they rarely reveal their true selves. “When you get a glimpse behind the façade that they put up, they’re completely different people,” he ranted. “We should stop pretending that they’re not and they should stop pretending that they are these paragons of virtue and beacons of decency.”

King’s response: “So are you saying that all politicians hide themselves from us, their real selves? Is that what you’re saying?”

Stewart’s silence was followed by a heavy sigh before he finally spoke. “Please tell me you didn’t just ask me that.”

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.

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.”