Angry Optimist: The Life and Times of Jon Stewart

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.

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.

“One of the things that appealed to me about the story is that it does have lighter moments,” said Stewart. “One of the things that kept Maziar alive was his ability to keep his sense of humor—to remember about joy and laughter—and see the absurdity of his situation.”

Next, Earth (The Book): A Visitor’s Guide to the Human Race, was published in September 2010, the second book Stewart created with his Daily Show roster of writers. He welcomed the novelty of writing the book in contrast to writing for the show. “The show can feel very ephemeral,” he said. “You work really, really hard every day to put it out there, and some days you’re successful with it and some days you’re not. That can be forgiving as a process, but there’s not much time to savor anything either.”

Just like its predecessor America (The Book), Earth hit the top of the New York Times bestsellers list the first week it came out. The premise of the book was to serve as a guide to help aliens understand earthlings—who, by the way, have become extinct according to the book—again patterned after a standard high school textbook. Publishers Weekly gave the book a starred review, writing, “In place of skits there are elaborate, color illustrations accompanied by captions written with his trademark deadpan humor; for instance, a photo of a mother and baby elephant holds the caption, ‘advances in contraception and industrialized food production allowed modern couples to have fewer offspring, while leaving the total weight of families constant.’”

New York Times critic Janet Maslin recommended the book, albeit with a few reservations. “The book, like the show, is best when it takes on subjects of real substance,” she wrote. “The funniest material is about religion and science… the calendar of December religious holidays for all persuasions [and] the claim that the word Torah is ‘German for kindling.’”

Yet other reviewers weren’t as impressed. “The main problem might be the conception itself,” noted critic Steve Weinberg in the Christian Science Monitor. “A posthumous pseudo-document for discovery in the future by vaguely imagined aliens probably seemed like a superb idea when conceived. But it is actually an idea that stretches credulity, even in a book that does not need to feel ‘real.’”

Meanwhile, Stewart maintained his regular schedule of putting out The Daily Show. “Free time is death to the anxious, and thank goodness I don’t have any of it right now,” he said. He was also thinking of another project, and though he knew it was a long shot, Stewart began to openly ponder the idea of launching his own news network, one that would stray from The Daily Show’s formula of fake news and deliver real news through a filter that was not found anywhere on television.

“If somebody wanted to start a twenty-four-hour news network that would focus on corruption and governance as opposed to the politics of it, do you think that that would have a chance to be successful and change the way debate occurs in the States?” he asked.

In lieu of starting his own news network, Stewart opted to take a baby step in the interim by instead launching the Rally to Restore Sanity, which most people saw as a satirical response to a “Restoring Honor” event that Fox News commentator Glenn Beck held in August 2010. Beck’s rally went head-to-head against another rally managed by Al Sharpton that same day to honor the Great March on Washington that Martin Luther King, Jr., spearheaded forty-seven years earlier.

“The rally is like everything that we do, it’s merely a construct,” Stewart said. “It’s just a format in the same way that the book is a format or the show is a format. [They all] translate the type of expression that we do, and it’s to be filled with the type of material that Stephen and I do, and the point of view.”

Though Stewart’s rally began as a joke on his show, public support quickly grew and Colbert joined in with his idea for a simultaneous March to Keep Fear Alive rally. The two promoted their respective events on their shows, and soon crowd estimates grew to almost seventy thousand people—thanks to a Facebook page set up for the event—which necessitated moving the rallies from the Washington Monument to the National Mall.

In promoting the rally, Stewart maintained that it was intended to send the message that the vast majority of Americans—from 70 to 80 percent—who are more moderate in their political beliefs, get drowned out by the vocal and extreme minority. He coined the rally’s official slogan: “Take it down a notch for America.”

“That was the point of the rally,” he said, “to deflate that idea that that’s a real conflict: red vs. blue, Democrat vs. Republican. I feel like there’s a bigger difference between people with kids and people who don’t have kids than between red states and blue states.”

As news and plans for the rally started to unfold—along with requests for press passes from media from around the world—people who couldn’t attend planned for their own rallies to occur simultaneously with the D.C. event. Even President Obama weighed in on the event, saying he was “amused” when he first heard about the rally. And both Colbert and Stewart took advantage of the interest to encourage attendees to donate to several nonprofit organizations, including DonorsChoose.org—a favorite charity of Colbert’s where public school teachers post classroom projects that need funding and people can donate money online—and the Trust for the National Mall.

Celebrities from Sheryl Crow to Ozzy Osbourne showed up, and the artist formerly known as Cat Stevens, now called Yusuf Islam—who rarely performed in public since officially retiring from the music business following his conversion to Islam in 1977—sang his signature anthem “Peace Train” with Stewart. But the gist of the show consisted of Stewart and Colbert in ramped-up versions of both their characters, building their individual cases—Stewart for the middle ground and reason, Colbert for encouraging people to be fearful of everything under the sun, as dictated by both media pundits and politicians alike—before Stewart took the mike and addressed the crowd in an artful, heartfelt speech that caught many in the crowd off guard, since it showed a sincerity rarely glimpsed on The Daily Show, last seen during his opening monologue on the first show after returning to the air after September 11, 2001.

“The press can hold its magnifying glass up to our problems, bringing them into focus, illuminating issues heretofore unseen, or they can use that magnifying glass to light ants on fire and then perhaps host a week of shows on the sudden, unexpected flaming ant epidemic,” he told the crowd. “If we amplify everything, we hear nothing. The press is our immune system. If it overreacts to everything, we actually get sicker… and perhaps eczema.”

Not surprisingly, he then turned his attention to politicians and the government. “We hear every damn day about how fragile our country is, on the brink of catastrophe, torn by polarizing hate, and how it’s a shame that we can’t work together to get things done, but the truth is we do,” he continued. “We work together to get things done every damn day. Most Americans don’t live their lives solely as Democrats, Republicans, liberals, or conservatives. Americans live their lives more as people that are just a little bit late for something they have to do, often something they do not want to do. But they do it, impossible things every day that are only made possible through the little, reasonable compromises we all make.”

For the first time in his life, in that fifteen-minute speech, Jon Stewart finally revealed a little bit of the man behind the desk. “After twelve years, [I felt] I’d earned a moment to tell people who I was.”

On the day of the rally, officials estimated the crowd at 215,000, which far outnumbered the estimated 87,000 attendees at Beck’s rally.

While Stewart was overwhelmed by the response and support at the rally, he was also surprised when a realization bubbled up from out of nowhere while he addressed the crowd. “When you’re standing at a rally and there are a hundred thousand people… [t]here’s an incredible urge to go, ‘I have the answer! Follow me!’” he admitted.

At the same time, he clearly understood that while many people thought Stewart was stepping out from behind his desk because he could clearly have a big effect and change some vital component of either politics or the media, that was never his intention in planning the rally. “I can understand the frustration of people who would be in that audience and think, ‘you’ve been complaining for twelve years, this is your chance to stop whining and do something,’” he said.

Afterward, he had to run interference and reinterpret his aims for the media, because some people—at the rally and those who viewed it on TV—misinterpreted his intentions, perhaps thinking he was presenting a serious event to encourage people to get involved in politics. Some even ventured to guess that Stewart was using the rally as a way to test the waters for his own future political campaign, but all along he maintained that it was meant to be no more than a parody while spotlighting his view that most people agree with “the idea that the conflict [in America] is left versus right when it’s actually corruption versus not-corruption.” And though Stewart’s political leanings are crystal clear to even an occasional Daily Show viewer, he wanted to convey the idea that neither left nor right is blameless since “both sides have their ways of shutting down debate.”

So he made a rare appearance on The Rachel Maddow Show on MSNBC a couple of weeks later to clear things up, but if anything, he only ended up muddying the waters further. “Whenever you go out there, whatever you put out, you can only control your intention,” he told Maddow. “You can’t control its perception or how people receive it, [but] you can control your execution.”

At times, things got a little testy between the two. “I feel like we’re doing the same thing,” said Maddow. “We both have a commitment to not lying, to telling the truth where we see it.”

But Stewart clearly disagreed. “You’re in the playing field; I’m in the stands yelling things.”

In the end, the two came to an uneasy truce that was still filled with mutual admiration. And perhaps it was no surprise when Glenn Beck, the inspiration for the rally, weighed in, critiquing the Stewart/Colbert event as on the same level as “a high school play: not good,” though he did acknowledge his admiration for Stewart. “Jon Stewart is very funny, and if I were in his position, I’d be doing a lot of the same things,” said Beck. “He takes things out of context—no worse than most of the other mainstream media—and is more interested in being funny than trying to actually understand the key messages in [my] show. I don’t think he’s looking for a Pulitzer, but his ratings are good. Good for him, keep doing what he’s doing.”

Beck maintained that Stewart was merely conveying the same message that he himself did in his August rally. But unlike Beck, Stewart was “co-opted [by the liberals]. I don’t think he liked it… he was used,” said Beck. “[When] the president himself promotes the rally, it becomes a mouthpiece for the [Democratic] Party, it became just another campaign stop. I don’t think that’s what Jon Stewart intended.”

“Just because Jon Stewart makes fun of it doesn’t mean he’s right,” said Jeff Zucker, president of CNN.

Still, Stewart’s message was heard by some. MSNBC’s Keith Olbermann revealed that he was taking Stewart’s advice to heart and would discontinue his nightly “Worst Persons in the World” segment on his Countdown show. “Its satire and whimsy have gradually gotten lost in some anger,” Olbermann explained. “So in the spirit of the thing, as of right now, I am unilaterally suspending that segment with an eye toward discontinuing it.”

The criticism continued that Stewart was intentionally blurring the lines again. “There will be some commentators questioning whether Stewart and Colbert crossed the line from comedians to political commentators,” said Pete Dominick, the commentator who had worked as the warm-up comedian for both Colbert and Stewart. “In all honesty, I’d say, yeah, I think they did make a political stance at the rally. The fact is comedy is an art form, and comedians are artists. You can’t be passionate about something and not have some part of yourself and your beliefs shine through.”

Yet again, Stewart denied it. “My job is to make jokes,” he asserted. “I don’t solve problems. If my job became solving problems, I would suddenly become a lot less good at what I do, unless the problem being had by the country was a lack of jokes.”

There was one bit of criticism that he took to heart in the rally’s aftermath. Author Salman Rushdie called Stewart to complain about having Yusuf Islam appear at the rally, since years earlier the singer had publicly supported the Islamic fatwa calling for the death of Rushdie, which had come about after publication of his best-selling novel The Satanic Verses, which many Islamic followers believe criticizes Islam and the Koran.

Yusuf Islam gave a speech at London’s Kingston University in 1989 in which he said, “[Rushdie] must be killed. The Qur’an makes it clear: if someone defames the prophet, then he must die.”

In an interview that same year, Yusuf Islam had said he’d be willing to carry out the execution of Rushdie if “ordered by a judge or authority to carry out such an act.” When questioned about a demonstration where a group planned to burn Rushdie in effigy, Islam commented, “I would have hoped that it’d be the real thing.”

After the rally, Stewart dismissed Rushdie’s concern, to the author’s great dismay, telling him, “I’m sure he doesn’t believe that people should be put to death for apostasy. I’m sure the guy isn’t really like that, let me talk to him.”

He spoke with Yusuf, who initially denied that he agreed with the fatwa, but soon shifted into his default mode of defense, asking Stewart, “Why do you have to insult the prophet?”

“We get into a whole conversation, and it becomes very clear to me that he is straddling two worlds in a very difficult way,” said Stewart. “And it broke my heart a little bit. I wish I had known that, I wouldn’t have done it, because that to me is a deal breaker. Death for free speech is a deal breaker.”

At the time of their conversation, Yusuf had been booked to appear on both The Daily Show and The Colbert Report, but both ended up canceling his appearances.

Not all critics disliked the rally, though, and the two-hour live broadcast of the rally was nominated for four Daytime Emmy awards, including Outstanding Special Class Special and Outstanding Special Class Writing.

To further add to his workload, Stewart was helping his wife, Tracey, to launch and operate Moomah, a children’s play space in Manhattan’s Tribeca neighborhood which opened in 2009 that also offered art classes and workshops and a café with coffee and healthy dishes.

Despite being a celebrity wife, Tracey still found it difficult to navigate the city with a baby—or two—on her hip when her husband wasn’t by her side. “Prior to having children, I loved going out to eat, being in my neighborhood, and visiting with my neighbors,” she explained. “When I was pregnant, same thing. People open the doors and they’re happy to see you, but the minute that baby is on the outside of you, they want nothing to do with you.” She did the typical mommy-and-me classes and other activities, “dancing around with the baby and singing really terrible songs, but I wanted to shoot myself in the head,” she admitted. If “the place was welcoming to kids, the music and food were terrible. I knew I wasn’t the only one that was feeling like this.” Thus, the idea for Moomah was born.

And she decided to add the art component to the café because she was unhappy with the kinds of children’s art classes that were offered in her neighborhood. “I started to get frustrated with what was being offered to my kids,” she said. “I would send my kids out to an art class and they would come home with a piece of construction paper with some glitter on it and I’d [think], ‘This is what you did with my kids’ time?’”

So with Jon’s blessing, Tracey opened the kind of neighborhood place where she’d feel comfortable—along with her kids—and named it Moomah, which was what she had called the security blanket she had when she was a kid. “I wanted it to be like a security blanket for moms.” And she decided to make creating art the focal point of the business partly because in addition to working as a veterinary technician, Tracey also had a background in art—she’d earned a degree in design and business from Drexel University and redesigned the lobby and offices of the Columbia University Clinic for Anxiety and Related Disorders—and partly due to her own anxiety issues. “Since I suffer from anxiety, the art projects help me find some peace of mind during the day.”

From the beginning, Moomah was a hit. One reviewer said, “Moomah offers a killer parent-kid recipe: it’s part café, part gymnasium, part art gallery, and part eco-exploratorium.” And Jon helped out occasionally. “When we get in a bind business-wise, we always say, ‘What would Jon Stewart do?’” said Tracey. “He advises us over the phone and has lots of ideas.”

But the business soon ran into trouble and began losing tens of thousands of dollars each week, so Tracey decided to temporarily close the business in January of 2012 to regroup. “I couldn’t get on top of my labor costs,” she said. “I had a lot of teachers working who were staffing the art workshops all day.”

Moomah didn’t stay closed for long. “I was completely overwhelmed by the emotional response from my customers [when it closed],” said Tracey. “I didn’t realize how much a part of the community it was.” She radically scaled back from twenty-seven employees to just five, and scaled back the workshop hours along with the menu when she reopened the business in May of 2012.

However, just two months later, she decided to close the business permanently and convert the idea of the business—making a space where moms could make art and feel comfortable—to an online magazine at moomah.com.

As it turned out, her husband was in the process of gravitating toward the very same thing: finding a place where he could make art and feel comfortable.

Only he’d have to travel almost six thousand miles to do so.