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Macmillan Childrens Publishing Group

Angry Optimist

The Life and Times of Jon Stewart

Lisa Rogak

Thomas Dunne Books



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.

The area around Princeton had long leaned toward white Anglo-Saxon Protestantism, and though the Princeton Jewish Center existed, that was about it when it came to Jewish culture in the area. Not only was young Jonathan teased about his height—or lack thereof—but for his name and heritage as well. "Leibotits" and "Leiboshits" were two of the more commonly hurled epithets. "I didn't grow up in Warsaw, but it's not like it wasn't duly noted by my peers that's who I was," he said, adding, "there were some minor slurs." One day in seventh grade he was beaten up by a group of kids while he was waiting for the bus, although he realized that he was at least partly to blame. "I was holding my books and a trellis I had made in shop and thinking, ‘How much more of a pussy can I be?'"

Jon took up the trumpet in elementary school and quickly showed that he had a talent for it. He joined a band made up of kids that played big band music with a repertoire that included songs like Glenn Miller's "In the Mood" and Duke Ellington's "Take the ‘A' Train." The band of nine- and ten-year-old musicians performed at school and community functions, and also regularly played at a home for juvenile delinquents that is today known as the New Jersey Training School.

In 1971, Jon made his first television appearance ever when the band was invited to play on a children's show known as Captain Noah and His Magical Ark, a mainstay children's program on the Philadelphia TV station WPVI that was a must-see for kids in the area. Captain Noah was founded by a Lutheran minister who hosted the show along with his wife. Though the show and characters were beloved by parents and children all over eastern Pennsylvania, Jon got his first glimpse of the gulf between what appeared on your TV screen and what happened behind the scenes.

"Captain Noah didn't know anything about kids," said Stewart. "He wasn't a happy guy. You'd see him slide down the slide and say hi to the kids, but there was more to it than that. Essentially, Captain Noah was a mean man who craved a smoke. Those are my memories of breaking into showbiz."

Though in later years Jon would say he had a normal childhood and only learned to develop a keen albeit thinly veiled barbed sense of humor because of his height-challenged stature, the truth is that while those may have been contributing factors, the thing that eventually set him on the path of becoming a comedic star was the direct result of a major tragedy of young Jon's life. After all, it's the rare—possibly nonexistent—amateur or professional comedian who doesn't experience a childhood tragedy—or several—in one form or another.

Jon Stewart was no exception.

To be sure, Donald Leibowitz wasn't overly warm toward his sons or his wife, but that was the norm in an age where fathers worked all day while mothers stayed home and kept house and raised the children. With hardly a kind or encouraging word toward his younger son, Donald had another reason to keep his thoughts and affections to himself: he was having an affair with his secretary. Though it was unclear how long it had been going on when he broke the news to his wife, the Leibowitz family would never be the same.

Back in 1973, when Donald revealed his infidelity and then subsequently moved out, divorce was still a rare-enough occurrence in the United States. Still, after Jon's father admitted to the affair, his parents separated and then divorced.

Ten-year-old Jon was devastated. Marian returned to work as a public school teacher while she and her children learned to manage with less. For instance, when Jon's older brother, Larry, had had his bar mitzvah two years earlier, when the family was still intact, they could afford to spring for a posh celebration and threw an elaborate party at a hotel in nearby Somerville. Jon's bar mitzvah, by contrast, occurred after his father had moved out, when finances were tight. As a result, his coming-of-age ceremony was held at the Princeton Jewish Center, where they also attended High Holidays.

Marian and her sons adjusted the best they could. "She was an anomaly in that era," Jon said. "She had a quiet confidence because she had to fend for herself."

After the divorce was final, Marian, Larry, and Jon got on with their lives. They spent a lot of time with her family, and one of Jon's favorite things to do was to go to the Jersey shore.

"I always loved going there," Stewart said. "When my grandparents were still alive, we would go to Asbury Park. When I was in my teens, we would go to Seaside Heights, or if we thought we could get into a bar illegally, we would go to Wildwood. If it was a family thing, we would go to Long Beach Island."

But despite the supportive extended family, Jon was often angry, though he tried his best to keep it under control. He was not only mad at his father but at a number of things that were going on in the early to mid 1970s. The area around Lawrenceville in central Jersey was overwhelmingly Republican and conservative at the time, when the rest of the state was engulfed in the protest against the Vietnam War and President Richard Nixon. He grew up during Watergate and Vietnam, and was "infused with a healthy skepticism toward official reports," he said.

He also cut off all contact with his father, refusing to have anything to do with him. Jon's rage was only fueled by his prodigious reading habit, particularly science fiction novels by Kurt Vonnegut and Aldous Huxley.

To avoid getting beaten up, he also worked on developing his sense of humor, in school and out, though he recognized that he had a lot of work to do. "No one has wit at eleven, you're just obnoxious," he said.

By watching and listening to others before coming out with a humorous response, Jon was not only building his own unique style of comedy, he was also in the process of realizing that his own poor view of himself was of his own making. "Those feelings of inadequacy were placed there by me," he admitted. "In my own head, I was a weirdo."

But young Jon was a quick learner. In studying various people in order to formulate the funniest reply possible, he soon realized his strengths as well as his weaknesses. For one, it was hard not to feel like he was inadequate when compared to his brother, Larry, who excelled in academics while Jon was an average student who specialized in wisecracks. "I remember being a young kid and seeing him have the Latin Cup from Lawrenceville Prep School, and I just thought, ‘Wow! I'm never going to be good enough in Latin to get a cup,'" said Jon. "So I thought I'd better take another route to get attention because, you know what, he's got me trumped on the smarts thing. I took my identity from wising off: smart-ass versus smart."

But he didn't attend Lawrenceville Prep like his brother; instead he entered his freshman year at Lawrence High School in Lawrenceville—other famous alumni at the public school would include Tom Cruise and Michael Eisner—trying not to get beaten up or bullied while learning how his own worldview could make people laugh. Though not all of his teachers would encourage his tendency to crack a joke or be class clown, others encouraged him. According to Larry Nichol, who taught Stewart English in his senior year, "He'd always be saying something on the way out the door as the bell was ringing."

Selma Litowitz, another English teacher, also encouraged her young student. "Jon has said that she was the first who recognized that his humor was something that he could make a living at," said Debra Frank, Litowitz's daughter. Incidentally they lived on the same street. "His joke was that, for many years, he thought that Jews had to live alphabetically."

He always liked sports, and he managed to find one where his small stature wouldn't put him at a disadvantage: he joined the varsity soccer team. The players practiced in all kinds of weather at the fields of nearby Mercer County Community College. "It would be twenty degrees out and the ground would be frozen solid, and we would be out there running around like idiots," he said, adding that working-class Lawrenceville was more of a soccer town due to the high percentage of immigrant families in town, mostly Italian and Polish. In upper-class Princeton, kids gravitated more toward football.

"I began my sports career as a way out of the suburbs," he admitted. "The best way to describe my ability was to say that after the game the other kids would say to me, ‘Way to try!'" Stewart and a friend from up the street spent hours practicing their moves every night, sometimes until midnight. "I spent hours just kicking a ball against a wall, doing anything that would help me get better," he said. "It's always been a part of my personality to be very dogged when I'm unsuccessful."

* * *

Though he loved soccer, and was pretty good at it—he actually made the all-state team as an honorable mention—Jon was happiest when pursuing a number of different interests rather than focusing on just one. His tendency toward being a Renaissance man, interested in pursuing everything at least for a short time, blossomed during high school. In addition to playing soccer and being in the school band, he also pursued his desire to work at an incredible variety of jobs, no matter how menial or dangerous. After all, unlike his brother, Larry, who knew he wanted to make his fortune in the financial world, Jon had no idea what he wanted to do and figured he'd try as many jobs as possible in order to check things off his list.

As it turned out, this approach would provide great fodder for a budding comedian. And regardless of the type of work, he could always count on having a new audience where he could pass the time trying to get a laugh out of his coworkers. He took his first job at the age of fourteen in what would become a long string of minimum-wage positions at the Quaker Bridge Mall just outside Trenton; in just over a year, he'd be fired from six different stores at the mall, in some cases because he wanted to make the other employees laugh.

First up: his brother Larry hired him at a department store as a stock boy. Jon gathered up his coworkers and decided to get a laugh the old-fashioned way: with a pratfall into a beanbag chair. Instead of hitting his target, he landed on a display case of aquariums filled with live fish which were soon flopping around on the floor gasping for breath. His mishap resulted in thousands of dollars of damage, and Jon tried to clean up as best he could by disposing of the dead fish into an incinerator, but his brother caught him and fired him before the end of his first day.

But there was another, deeper reason why young Jon made the leap in front of others: he felt like he was born to get in trouble. In fact, he actively pursued any opportunity to test the limits, whether or not there was an audience watching.

"When you feel like you want to express yourself, you need an impetus, a catalyst," he said. "And part of the catalyst is to get yourself in trouble." In addition to being on crutches at his own bar mitzvah because he had broken his ankle playing basketball while on a skateboard, he can rattle off a long list of physical injuries caused by his intentionally trying to get into trouble.

"I'd say ‘hey, you see those logs that go up there? I bet I could jump over that.' I went to the emergency room a lot."

Next up: a job as baker's helper and cleaner at a bakery at the same mall. "My job was to wash these huge silver barrels that they made the bread in," he said. "So I would line the barrels with soap and then fill them with water. One day I forgot about the soap and went to scrub tables. Well, the bakery people thought I lined the barrels with flour. Apparently a lot of people found themselves in the mall bathroom that day."

In his senior year, he signed up for the chorus in the annual school musical, The Pajama Game, primarily because most of his friends were in it. For one number, the male singers had to wear spats, but since nobody could afford them, they wrapped white tape around their shoes so they'd be visible from the last rows of the auditorium. "Everybody was meticulous about it except me," said Stewart. "I wrapped my shoes up so that it looked like I had an ankle injury or gout. I remember everybody making fun of me."

Later in the show, he decided to make the audience laugh. In a scene in front of a backdrop of trees, the male and female leads were starting to sing a duet where they profess their love for each other, but Stewart had other ideas. In fact, he couldn't help himself. "I wandered out and put my back to the audience and pretended I was relieving myself on one of the trees," he said. "The crowd found this somewhat amusing, the two actors on stage, not so much. I thought, ‘Oh, my God, I'm killing. This is awesome! This play is going great.'" While he obviously loved the audience's reaction—and the ego boost that came from making a large group of people laugh—Jon was also beginning to see that there was a time and a place for comedy. "I had to learn when and how to use it, but by God, there's nothing else I could do."

He was discovering that he could be powerful through his use of comedy in a way that was impossible in other parts of his life.

"I was obnoxious, and people in New Jersey in the late seventies dug that, man," he admitted. "My role in every social interaction was always as the wisecracking runt who had big friends," he said. "I think that's where I got it. That was my role in the group: basically to get my friends into fights."

In fact, he credits his short stature with helping him to decide to pursue a life of comedy, though it would still be a few more years until he fully committed himself to that career. He theorizes that if he'd even been a few inches taller he's not sure if he would have gone into comedy at all. "I don't know if I would have tried so hard," he said. "I had this vision that life would be peach pies and candy creams if I was six foot two. But if I had been physically bigger, I probably would have wasted even more energy than I did, thinking I was going to make sports my life."

"Those are the makings of a great comic," said Chuck Nice, a fellow comedian. "You're bullied, you're smaller. What you end up doing to survive is to develop a great rapier wit and the ability to make people laugh."

"I think there are virtually no comedians out there who are handsome, well-adjusted, popular, or come from extremely loving, wealthy families," said Devin Gordon, formerly a senior writer at Newsweek. "Those people tend not to go into comedy."

Stewart began to study how famous comedians of the time operated, their style, particularly his idols Woody Allen, George Carlin, Steve Martin, and Lenny Bruce. But despite watching them on talk shows, Jon didn't think to aspire to become a talk-show host. "I never watched talk shows when I was a kid and thought, ‘Wow, that's a cool thing to do,'" he said. "Like, if I was watching Carson or something I was more impressed with the fact that I was up at eleven o'clock at night."

He was also making his first forays into learning about politics, and testing the waters to discover what his own views were. Before then, he'd only thought about causing trouble. When he was nine years old and traveling with his big band to concerts, he was in a Manhattan hotel room looking down at the street where a van for President Nixon's reelection campaign was parked directly below. "I was thinking, ‘If I spit from here…'"

Now, though, his ideas were more well-formed. He described himself as being "left-leaning" and "very into Eugene Debs," a union leader and five-time presidential candidate running under the Socialist Party banner between 1900 and 1920. During a debate in a high school class, Stewart had to pretend he was Ronald Reagan, at the time a presidential candidate whose worldview and political affiliation was the polar opposite of Debs. "I had to defend my increased military spending," Stewart remembered.

Then, at the age of fifteen, he had his first epiphany about how his life could be different, courtesy of another New Jersey native, Bruce Springsteen.

"The first time you hear Darkness on the Edge of Town, you begin to plan how to move out of New Jersey," he said. "When I listened to his music I didn't feel like a loser, I felt like a character in an epic poem about losers. You felt like there was possibility. That here is a guy who grew up like you grew up and had that same feeling of, I bet if I just fucking get in the car and drive, there will be an opportunity for something different and better—an opportunity to be something that I want to be."

And he was starting to think that that "something" involved making people laugh. He was encouraged when he was voted "best sense of humor" in the 1980 graduation class at Lawrence High School.

He hoped that the next four years, which he'd spend at The College of William & Mary in Williamsburg, Virginia, would help him figure that out.

Copyright © 2014 by Lisa Rogak