Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

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  For Melanie Vanni, who likes Jon Stewart because “No matter what’s coming down the pike, he’s hilarious, he’s commanding, he’s E. F. Huttonish…”

  Also for Seth J. Bookey … this book would have turned out a LOT differently if it wasn’t for his judicious help and persistent and inquisitive eye.

  CONTENTS

  Title Page

  Copyright Notice

  Dedication

  Introduction

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Chapter 10

  Chapter 11

  Chapter 12

  Acknowledgments

  Notes

  Index

  Also by Lisa Rogak

  About the Author

  Copyright

  INTRODUCTION

  LET’S GET SOMETHING out of the way from the beginning:

  Jon Stewart is a bundle of walking contradictions. On the one hand, he makes no bones about exactly how he feels about things at any given moment, delivering his opinions and thoughts to his audience seriously—usually with an eye toward making them laugh—while also hopefully making them question the way the world works.

  On the other hand, he is a man who hides in plain sight. Stewart is an enigma who shuns the spotlight, and his contempt for certain people and philosophies sometimes makes him so enraged on the show that he starts to shake and spit.

  “[I’m] a bitter little hairy man of comedy,” he has joked.

  Actor Denis Leary predicted his friend’s progression way back in 1994 during Stewart’s first talk show: “Jon’s shown more of his nice-guy side so far,” he said. “As the show continues, it will get uglier. Eventually it will just be this raging little Jewish man screaming into the camera.”

  Some days, indeed, that man seems not so far away.

  At the same time, the man is comprised of a peculiar mix of anger and optimism, in almost equal proportions.

  But the inescapable truth is that Stewart is so damn funny that even the targets of his often caustic observations appreciate his jokes and even laugh at their own foibles as expressed through his eyes.

  By his own account, Stewart says he was born with an unorthodox sense of humor that needed to be let out. “I can’t remember not being this way,” he said. “I can’t remember one day thinking, ‘You know what might work for me? Humor.’ My brother was smart, so there was no way I was going to cop that title in the family, so I naturally gravitated toward another direction of attention: I was the court jester of the family.”

  At the same time, his humor leans toward taking the side of the underdog.

  “He has this internal barometer of what’s right and wrong,” said Madeleine Smithberg, former Daily Show producer. “He has a very sensitive justice meter. He’s just way too smart for that little body.”

  “My comedy is about anything that, when I was growing up, made me feel different or disenfranchised in any way,” he explained.

  As a result, he developed the tendency to constantly look over his shoulder. “I’m nervous about everything,” he admitted.

  “Jon is driven by the forces of guilt and shame and fear of being on the outside that give Jews their comic angst,” said Ben Karlin, who worked with Stewart on The Daily Show for many years.

  “Jon is a neurotic nut,” added comedy writer Adam Resnick.

  Stewart agreed, up to a point. “My comedy is not the comedy of the neurotic,” he said. “It comes from feeling displaced from society … because we’re not in charge.

  “But I am probably a lot more critical of things than I should be.”

  For someone who is so widely adored and respected, Stewart insists that his rise to stardom was unplanned. “People who worry about where they’re going next generally don’t end up where they think they’re going,” he said. “When you’ve got too much of a master plan, it’s going to fail.

  “As a kid, I never thought, ‘I want to be a talk-show host,’” he said. “Some people growing up gazed into the sky and every cloud looked like Johnny Carson. I just wanted to be a good comic. And that was only after I got out of school: ‘Well, what do I do now? I like to sleep late and I don’t like working.’”

  Critics, pundits, and fans all try to parse the man, sometimes from surprising corners—Republican congressman Paul Ryan has called Stewart the funniest man in America while New York Times columnist Paul Krugman accused Stewart of “ruining his brand” by dismissing the idea of a trillion-dollar coin—but really, he claims that what makes him tick is pretty simple:

  “I think of myself as a comedian who has the pleasure of writing jokes about things that I actually care about, and that’s really it,” he stressed. “I have great respect for people who are in the front lines and the trenches of trying to enact social change, but I am far lazier than that.

  “I am a tiny, neurotic man, standing in the back of the room throwing tomatoes at the chalkboard. When we come to work in the morning we say, ‘Did you see that thing last night?’ And then we spend the next eight or nine hours trying to take that thing and turn it into something funny.”

  Regular fans of the show know that in Stewart’s eyes, nothing—nothing—is sacred. His rapid-fire wit often paints him into corners with people who have every reason to be offended, but luckily they’re laughing their asses off instead of being outraged. Stewart was a frequent guest on the Larry King show and he liked to poke fun at the host while pointing out societal hypocrisy and expounding on the current topics of the day.

  “We think about all the wrong things rather than solve the problems,” he told the oft-married King back in 2004. “And we freak out by gay marriage. I mean, honestly, have you ever been in a gay marriage? I hope I’m not prying.”

  King’s response: “No, I have not.”

  Stewart: “I just thought, law of averages and all that. I mean, how many out of twenty, how many has it been?”

  King: “Stop!”

  Stewart: “Ten percent of the country is gay, and you’ve been married twenty times, so I figured two of them had to be—no?”

  * * *

  Stewart couldn’t stop being funny if he tried. After all, his humor has always been fueled by his deep sense of frustration at the injustice, lies, and hypocrisy that are everywhere he looks. “I’m attempting to scratch an itch, and I want to make humor about things I care about,” he said. “People always ask, where do the jokes come from? Really, they come from a place of pulling your hair out seeing things that make you cringe and wanting to turn that into something that will make you laugh.”

  At the same time, he has no tolerance for self-analysis or a woe-is-me attitude, which is perfectly understandable since being constantly attuned to something you could feasibly turn into a quick laugh—and ego boost—can’t help but turn your view outward, at least when you’re in front of an audience.

  So when Oprah put him on her couch in 2005 and promptly proceeded to start delving into the cause-and-effect of his life, he quickly waved away her probing questions.

  “If you looked at anybody’s life, you could find the pain in it and say that what they do is born of that pain,” he patiently explaine
d.

  But Oprah wasn’t done. When she asked if he was teased as a child, he’d had enough, and shot back, “Who wasn’t?”

  But he does admit that his childhood has unalterably shaped his life and sense of humor. “A part of me is probably still trapped in whatever emotional state I was in at fourteen years old, when my nose and head were the same size they are now, but my body was half its weight,” he said. “I think there’s a part of you that’s always stuck in that. And when you look in the mirror, and you evaluate what you’re doing, it’s always fractionally coming from that perspective.”

  While other comics with similar physical shortcomings may have woven an entire lifetime’s worth of routines around their imperfections, Stewart differentiated himself by steering away from it. Sure, he’ll allude to his height and ethnic background every so often, but it’s clear he finds it tedious to dwell on them. After all, his is a very specific type of comedy: no pratfalls, no physical pranks. Stewart’s brand of comedy emanates 100 percent from his brain.

  And he’s certainly found the perfect forum sitting behind The Daily Show newsdesk. While he will occasionally rail against the iniquities of the world away from his Daily Show pulpit, for the most part he keeps a very low profile, and is extremely private and protective of his personal life. Though he will occasionally indulge the paparazzi and allow them to snap a few pictures of himself and his family, photographers know that to camp out on his doorstep in Tribeca would pretty much be a huge waste of time, because once Stewart enters the building after a long day at the studio, he doesn’t leave until it’s time to head uptown again the next day for the painstaking, pressure-cooker process of putting the next show together. You’ll rarely see him mentioned in the gossip columns or read about him partying at some glam black-tie gala.

  “I have two speeds in my life,” he said, “pedaling a hundred miles per hour uphill to try and stay up, or sitting at home on my couch with a glazed doughnut on my lap staring at a Knicks game. I need downtime to refill the reservoir. I don’t have much of a life outside. It is all-consuming.

  “I should probably make [my] story interesting, but I got nothing,” he said. “I’m trying to imagine Kitty Kelley in here saying, ‘Let’s do a book’ and she’d be in here for five minutes and then she’d say, ‘You know what? Screw this.’”

  This biographer will tell you that yes, it’s been a challenge to research the man. Not only does Stewart keep a low profile whenever he’s not toiling away at the Daily Show studios, but his friends and colleagues are equally closemouthed about disclosing any quirks or stories about the man. But maybe that’s why his audience respects him so much, aside from the acerbic wit, the probing intelligence, and the eagerness to point out hypocrisy: because he’s not out claiming space in the tabloids or striving to increase his visibility or Klout Score, they trust him.

  He doesn’t much care about fame, and indeed, he never set out with grandiose plans for recognition in mind.

  “My goal was always to be better than I was at the present time,” he confessed.

  Yet, despite this laissez-faire attitude, Stewart’s always had a backup plan. After all, ever since his father left the family when Jon was ten years old, he’s always felt like the rug was about to be yanked out from under him. In yet another exchange on Larry King’s talk show, Stewart expressed mild outrage that anyone would consider him as someone who looks on the sunny side of the street.

  “I’m a Jew. What kind of question is that, are you an optimist? I always have my bags packed. Is that optimistic? I never know when they’re going to knock on my door and [tell me to leave]. There are very few countries that don’t have at least one museum going, ‘And this is when we chased you out.’ That’s why we’re all in comedy, we want to stay.”

  But it’s that same philosophy that has lent a certain degree of flexibility to Stewart’s life. After all, while he worked his tail off for years to reach his current level of fame and stardom, his belief—warped though it may be—that it could all disappear tomorrow afforded him an outlook that was all too rare in an industry where many people automatically assumed they were destined to be stars. Of his early days in comedy, he said, “I had to make peace with the fact that if this works, great, and if it doesn’t, I had to be okay with that, too. You can’t go into it thinking, ‘If I do this and they take this away, what’s going to happen to me?’ You have to know that you can always open an ice-cream store.”

  And while Stewart may jokingly dismiss any suggestion that he is an optimist at heart—he would never deny the fact that he is indeed at times a very angry man. Yet if he didn’t wholeheartedly believe that he could bring about real change for the better in the government, the world, even his own neighborhood, he would have no reason or motivation to work as hard as he has to attract attention to the issues that are near and dear to his heart.

  And that is the definition of an optimist in any book.

  “The idea that I get to do this for a living is mind-boggling to me,” he said. “It really is sort of a dream life.”

  But that’s not how things started out.

  CHAPTER 1

  WHEN JONATHAN STUART LEIBOWITZ was born on November 28, 1962, in New York City to Donald and Marian Leibowitz toward the end of the huge postwar baby boom, he began a typical middle-class American childhood that was unremarkable for the time, and apparently very much strived for by the majority of people in the United States.

  He joined Larry, a brother who was two years older, and the Leibowitz family had little to set it apart from the other families living in Lawrenceville, New Jersey, just down the road from Princeton, in all ways but one. As one of only a handful of Jewish families who lived in the area around the famed Ivy League school—notorious as a well-heeled Protestant college that was rumored to deliberately limit the quota of Jewish students admitted well into the 1970s—the Leibowitzes were determined to live an everyday—and secular—American life in the peaceful heyday of the early 1960s. As Stewart later put it, he never lived anything but a typical American childhood: “I grew up in the good old days before kids had these damn computers and actually played outside.”

  He watched popular TV shows like Emergency! and The Hudson Brothers Show, he ate Quisp cereal and collected box tops to redeem for cheap plastic toys, and developed the first crush of his life on Eve Plumb, who played Jan Brady on The Brady Bunch.

  “My life was typical,” he said. “I played Little League baseball. I never wanted for food. I always had shoes. I had [my own] room. There were no great tragedies. There were the typical ups and downs, but I wouldn’t say it was at all sad. We were Jewish and living in the suburbs so there was a slightly neurotic bent to it, but I can’t point to anything where a boy overcame a tragedy to become a comedian. As my grandmother used to say, ‘I can’t complain.’”

  Despite his apparently normal childhood, young Jon did stand out in one way: he was short. Noticeably so. His classmates towered above him, and so he made an easy target. And it didn’t take him long before he realized the best way to deflect his tormentors was with a witty comment or pointed retort.

  “I was very little, so being funny helped me have big friends,” he said.

  “I realized it was a way of getting attention pretty early on,” Jon added. “There was a sense that this feels good, to say something that made everybody laugh. It was a rhythm that made sense to me.”

  Though the Leibowitzes belonged to a local synagogue and Jon attended a yeshiva kindergarten before moving on to first grade at the local public school, neither parent was particularly interested in immersing themselves wholeheartedly in the Jewish faith. Possibly this was because of a lack of opportunities to do so in and around Princeton, but also because they hoped to distance themselves from their family history and blend into the community more easily. Donald’s grandfather was ultra-Orthodox; he ran a shoe store on the Lower East Side of Manhattan and never failed to wear his religion on his sleeve. “When we visited his store, he would
… make me recite prayers,” said Donald. His son—Donald’s father—had already begun the move away from a life of extreme religion by becoming a cabdriver in New York. At the time, running a store in an orthodox Jewish neighborhood pretty much ensured that few Gentiles would cross the threshold into the store; on the other hand, a cabdriver gave up control over the types of people he’d interact with over the course of a day.

  Marian’s family, by contrast, took a more secular route. According to genealogist Megan Smolenyak, Marian’s father, Nathan Laskin, was born in Inner Mongolia in 1906 and grew up in Tientsin, China, home to a tiny but thriving community of Jewish entrepreneurs and salesmen, many of whom built thriving businesses as furriers. Most of the settlers had defected from the Russian army after the Russo-Japanese War ended in 1905. According to Marian, Jon took after Nathan, her father, who had a wicked sense of humor and actually subsidized his salary as a fur salesman by moonlighting as a stand-up comic in China in the early part of the twentieth century and later immigrated to Seattle to help expand the business.

  Nathan helped run the Manchurian Fur Trading Company before he decided to pull up roots and try his luck at business in the United States. After first landing in Seattle, he eventually moved with his wife, Fannie, and small daughter, Marian, to Cooper Street in Manhattan, where he continued working in the family fur business. In 1940 he pulled in the princely sum of seventeen hundred dollars for the entire year.

  After Donald and Marian married in the late 1950s, they settled into life in Manhattan where Marian worked as a schoolteacher and Donald worked at RCA Labs in Princeton, New Jersey.

  Shortly after their first son, Larry, was born in 1960, Don and Marian decided to move from New York City to New Jersey to reduce the commuting time to Don’s job at RCA Labs. They moved into a house in Lawrenceville, the next town over, about forty miles from Philadelphia. As was typical of the era of the man in the gray flannel suit, mothers held down the fort at home while fathers spent long hours at the office, arriving home often too late to spend time with their children. And Donald was no exception.