Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  If he felt like an outsider in New Jersey, he was about to get a bigger shock: many of the students Stewart encountered at the college had never met a Jewish person in the flesh before. He was their first. He described them as “boys with eight first names, which also happened to be the names of Confederate generals, but who just went by ‘Trip.’”

  But Stewart didn’t pick the prestigious Southern university for either its academics or religious life: instead, he chose William & Mary so he could play soccer, which was much more important to him than studying and attending classes. He dreamed of playing professional soccer after graduation.

  Head coach Al Albert had built a strong nationally recognized men’s soccer team at the school, with numerous players going on to pursue successful professional careers after graduation, which would include Scott Budnick, Wade Barrett, and Jeff Agoos. This attracted Stewart’s attention.

  Plus, following the idea planted by Springsteen, at least it got him out of New Jersey.

  Once he was ensconced at the school, his life had an anchor in the form of daily practices and regular games. He started with the junior varsity team as a freshman before Coach Albert invited him to join the varsity team when he became a sophomore. Besides being a starter for the team, he even coached a local boys’ high school team at the nearby Gloucester High School. In fact, it was the first time in his life that he focused on just one activity: soccer. “My years with Tribe soccer were the best of my college experience,” he said.

  Stewart heads off the competition during a college soccer game. (Courtesy William & Mary)

  “I didn’t know how to be friends with girls; I knew how to hang out with guys in a bus traveling to soccer games, so that was my idea of fun,” Stewart continued. “The games were exciting, and there was a lot of passion, and for those ninety minutes it was wonderful.”

  But it didn’t come without a few bumps in the road. “Soccer was a gentlemen’s game, and occasionally there were times where the slur would be used,” Stewart recounted. “And my last name was Leibowitz and my nose was twice the size of my head, so it was not hard to figure out my ethnic background.”

  “His overall experience at William and Mary wasn’t as positive as a lot of people’s,” Albert said. “If it wasn’t for soccer, he would have left school. But soccer kept him in here. His connection through the school is the program.”

  He also worked to hone his comic chops on his teammates. “Some of the best people I have ever met, I met down here,” he said. “This was the first place I developed my humor.”

  It was the rare player who would attempt to out-joke him. “Jon’s wit was famous within the team,” said Albert. “No one would dare even then engage him in verbal combat. None of us imagined he would take things to the level that he has, but he was, even in college, a very funny guy.”

  “Everybody was … afraid of messing with Jon because he was so quick-witted,” agreed David Coonin, who played alongside Stewart.

  But even he admitted that not everyone appreciated his sense of humor. “[College] was the process where I was somehow trying to hone obnoxiousness into wit,” he said. “That is a process that doesn’t go easy, a lot of peaks and valleys. In general, William and Mary got more of my obnoxiousness than wit. But I had a great deal of pride in working my way onto the team and becoming a starter. It gave me the confidence that there was a correlation between working hard and success and results and getting better at something.”

  Despite the rigors of carrying a full course load at a demanding school, Stewart did the bare minimum when it came to academics. Though his initial major was chemistry, he switched to psychology before graduating.

  “Apparently there’s a right and wrong answer in chemistry, whereas in psychology, you can say whatever you want as long as you write five pages,” he joked. “The psychology degree comes from the fact that I was a chemistry major and they kept wanting the correct answer, whereas in psychology you basically write whatever you want, and chances are you get a B.”

  He also joined a fraternity, Pi Kappa Alpha, but ended up resigning after only six months because much of frat life revolved around the enforced bullying of both himself and others, and he had had enough of that during childhood. Unlike then, however, no amount of jokes could deflect the abuse.

  “Greek life [offered] a false sense of friendship and was an abusive relationship under the guise of camaraderie,” he said. “There are things that are good, but as fun as it was to have parties in that house, it wasn’t worth the pressure of living up to someone else’s expectations as to what you’re supposed to be, and going to meetings where they had parliamentary procedure to discuss a toga party.”

  After he quit the frat, he moved into a college-owned house at 111 Matoaka Court where the number one rule was, “Don’t touch the carpet.”

  “My college career was waking up late, memorizing someone else’s notes, doing bong hits, and going to soccer practice,” he said.

  He also found time to date and, according to some, had a great deal of success despite his self-consciousness about his height. “Jon was very popular … and dated some very attractive women in college,” said John Rasnic, who played soccer alongside Stewart and also was his roommate for a time.

  Jon’s photo from a soccer program at William & Mary. (Courtesy William & Mary)

  At least with some other students Stewart’s Jewish background was never forgotten. Teammate Rasnic recalled that a player on an opposing team from Randolph-Macon College, another Virginia-based school, called Stewart a kike. “Jon was a little upset, I think, perhaps a bit surprised, but he didn’t let it bother him,” said Rasnic.

  One time, a group of students on an opposing team made a comment about the size of Stewart’s nose. Stewart responded that size had never been an issue for him, which elicited a roar of laughter from the crowd and instantly changed the atmosphere.

  “From that point on, every time he touched the ball they cheered for him,” Albert remembered. “And that was his ability to make people laugh and to win people over without making them agree with him. He was not a polished player and he didn’t have the pedigree the other players had, but he had some talent and I think he made the most of the talent he had.”

  In only two years of varsity play, Jon had developed into such an excellent athlete that Coach Albert invited him to join the U.S. squad of the best young Jewish soccer players from all over the country who were heading to the 1983 Pan American Maccabi Games in São Paulo, Brazil, the penultimate step before the World Maccabiah Games, essentially the Olympics for Jews. The World Games are held every four years in Israel with four different competitive classes including Open, Masters, and Disabled, while the Pan American Games rotated between countries in North, Central, and South America, also every four years.

  “When we walked on[to] the soccer field, they called us gringos, they wanted to know if we knew how to play,” he said. “After that, they no longer called us gringos.”

  Stewart’s accomplishments over four years of soccer primarily as a midfield defender at William & Mary were prodigious: in addition to scoring ten goals overall, he also made an impression in the 1983 ECAC tournament championship over the University of Connecticut by scoring the winning goal to defeat them 1–0. It was only the second time that the college won the conference championship.

  As graduation approached, however, his dream of playing professionally was growing dim. Injuries had plagued Stewart throughout his college career, and toward the end of his final season, he injured his knee to the extent that he was unable to play.

  However, despite the camaraderie he felt with the other members of the soccer team, Stewart spent much of his college years feeling like he didn’t fit in. And though he continued to use humor as a relief valve, he worried about his future despite his success on the soccer field. “I just didn’t know what the fuck I was doing with myself,” he admitted. “I was uncomfortable in my own skin, let alone being with kids who were not. So t
hat in itself was probably annoying.”

  Stewart’s senior photo from the 1984 Colonial Echo, the William & Mary yearbook. (Courtesy William & Mary)

  When he received his psychology degree in 1984, he had very little idea what his next step would be.

  “When I left William and Mary, I was shell-shocked because when you’re in college it’s very clear what you had to do to succeed,” he said. “You knew what you had to do to get to this college and to graduate from it. The unfortunate yet truly exciting thing about your life is there is no core curriculum. The entire place is an elective.”

  As he saw it, his only choice was to pack up and return to New Jersey.

  * * *

  Once he was back in the Garden State, he picked up right where he’d left off and began adding to the wide variety of jobs that he held in high school.

  “I’ve had an amazing amount of [lousy] jobs,” said Stewart.

  In 2013, genealogist Megan Smolenyak researched Stewart’s ancestral roots for the Huffington Post, and what she uncovered about his relatives’ diversity of occupations could be used to describe his occupational history precomedy as well. “His forebears have held one of the more eclectic mélange of jobs I’ve seen,” she wrote, “including taxi driver, fruit and vegetable peddler, furrier, shoe store proprietor, and window cleaner.”

  Though Stewart didn’t return to the Quaker Bridge Mall to check off the remainder of the shops and restaurants he could get fired from, he came close.

  One of his first postgraduation jobs consisted of testing mosquitoes for encephalitis in the New Jersey Pine Barrens, for which he received the princely sum of $119 a week for the summer. “I had a state car, I’d drive down to the Pine Barrens and think I had the greatest gig in the world,” he said. “We’d go out at night and set up these traps and then come back in the morning to [collect them]. Every flying creature in the Pine Barrens would be there.”

  The traps consisted of giant paper coffee cups wrapped in panty hose which were then attached to car batteries that powered both a light and a fan for each cup. “All the bugs would fly towards it, and they’d get sucked in through the fan and get trapped,” Stewart said.

  “We’d take them back to the lab and knock them out with chloroform and then sort them out by sex. This would take a while and they would start to wake up.” By the end of the summer, he said he looked like he had contracted bubonic plague, though only the female mosquitoes bit. “I had all sorts of chiggers and bites. It was insane.”

  Once that job ended, he continued on to a local science research lab, and he took a job where his tenure was mercifully short, for obvious reasons: “The scientists would pour radioactive chemicals into beakers and tell me to clean them out,” he said.

  Next, he took another job working for the state of New Jersey as a puppeteer putting on shows for disabled children with an organization called Kids on the Block. Some of the puppets were disabled, others weren’t, and Stewart performed skits designed to help teach kids without disabilities how to relate to kids with physical and emotional issues. “I was a cerebral palsy puppet, a blind puppet, a deaf puppet,… and a puppet who couldn’t commit to a relationship,” he said.

  “While the show was a noble effort, it was completely unsatisfying for me.… I needed to create something I felt part of.”

  His desire to make people laugh—on a larger scale than just his teammates or coworkers—was rapidly becoming part of his larger dream. “[The puppet show] was a truly good thing to do, yet I thought, fuck this. I need stand-up,” he admitted.

  In between nobler jobs such as the puppeteering, he also worked part-time as a bartender at restaurants and bars around Trenton. The irony wasn’t lost on him. “I was literally helping and hurting people, all on the same day,” he said.

  But he still had to make a living, so he ditched the puppet gig and ramped up his bartending gigs, driving an “off-brown” Gremlin back and forth to work while listening to his beloved Bruce Springsteen on the car stereo. The Bottom Half was the name of one bar, tucked into a windowless basement below a liquor store in Trenton; City Gardens, an alternative rock club, was another. Jon gladly worked shifts there since popular bands like the Ramones and Butthole Surfers played often, and in fact Joey Ramone became a regular customer.

  He enjoyed the work, the music, and clientele, and even invented a drink called A Whack in the Head, combining a Long Island Iced Tea with an Alabama Slammer. “Drink two, and you’re not getting up the stairs,” he joked.

  But despite his work and social life—he also played on a local softball team every spring—Stewart still felt like he was on the outside looking in, wondering why everyone else seemed so much more happier than he felt.

  “When I tended bar, I was always happier behind the bar, not out rocking to the band,” he said.

  In a way, he equated bartending with his glory days as a college soccer player.

  But the stress of cutting off drunks and watching other people have the time of their lives night after night took a toll. He decided he would be happier back at a more conventional job, and so hung up his bartending apron and once again took a job working for New Jersey state government, landing a position in the disaster planning preparedness department.

  Because he happened to be proficient at a new database program known as Lotus 1-2-3, he was assigned to make lists and keep figures on state resources.

  “I made charts … in case we were attacked by Pennsylvania,” he said.

  As usual, he was good at his job and his supervisors and managers loved him, but inside he just felt dead. He wanted to start doing something he felt was worthwhile along with developing his own identity—hopefully one that involved making people laugh, the only thing that made him feel normal, like he belonged—and so he weighed his options.

  “I was a little lost from the age of eighteen to twenty-four,” he said. “I was … working for the state and playing on a … softball team … thinking, this is it for the next seventy years? I realized that if I didn’t watch it, I’d be forty and this would be me, but instead of playing softball, I’d be the guy organizing the team.

  “Plus, they were about to re-up me for another forty years [at my job], and … I’m twenty-three.… I can always be one of the bitter guys in my town. It’s not like they won’t save a seat for me.

  “Besides, I’m way too young for a dental plan,” he joked.

  So he made his decision. Though he had shared with a few people his dream of making audiences laugh for a living, to his friends and family it still came as a shock when he broke the news. He had kept it mostly secret because he didn’t want anyone to discourage him or talk him into a life that included a safe bet: a job with the state, insurance, pension, the works.

  “I’d never told my friends or family … so to them it was like a bombshell.”

  But to him, it was the only thing that made sense. When watching comedy, he thought, “That’s how my brain works,” he said.

  “[I became a comic] because I was uncomfortable in other settings.… As bad as I was when I started, it still felt better than anything else I’d ever done.”

  “When he finally decided to become a comedian, it was a little bit of a shock,” said his mother, Marian Leibowitz. “But he was going to New York, he wasn’t going to China. I decided I wasn’t going to be the person to discourage him.”

  Stewart packed a bag, found a place to sublet in Manhattan, and left for New York City. “I threw everything away and moved to New York on a six-week lease,” he remembered.

  As usual, on the seventy-mile drive, Jon turned to his role model for a little boost in confidence. Years later, he’d tell Bruce Springsteen on The Daily Show how important his music was to helping him get on that very soundstage. “You go through the tunnel, take a chance, and you can work to get away from your circumstance. And by working to get away from your circumstance you can make something better of yourself, but there’s no guarantee. But you know what? The joy of it
is chasing that dream, and that was my inspiration for leaving New Jersey and going to New York. So I just wanted to thank you personally from the bottom of my heart for giving me something to put into the dashboard as I drove a U-Haul van through the Holland Tunnel.”

  CHAPTER 3

  IN 1986, JON STEWART risked everything to move to New York City to pursue his dream of becoming a stand-up comic.

  He had a small problem. After he settled into city life, it took him almost a year before he worked up the courage to go onstage in front of an audience for the first time. Of course, every budding stand-up comic needs time to prep, to develop a routine, to study every word and nuance of routines by the greats, but Stewart had another issue to face. He had never actually performed comedy onstage. The closest he’d come was his prank in the musical during his senior year. He was at a clear disadvantage compared to the seasoned comedians who went from one open mike to another in the course of an evening.

  While he had plenty of experience cracking jokes with his friends or while standing behind the bar, Stewart had never told jokes onstage.

  He was understandably terrified.

  “I was in the city for a good nine months to a year before I had the balls to go up onstage,” he admitted.

  So while he worked up the courage to walk through the doors of a comedy club that held regular open mikes where anyone could tell a couple of jokes at least for a few minutes before getting heckled off the stage, Stewart continued his habit of working odd jobs: driving a catering truck to deliver food to fancy events around town or busing tables at a Mexican restaurant, all while listening to Lenny Bruce records in his off hours. He had a vague notion that if comedy didn’t work out after a while, he’d apply to law school.

  After months of putting it off, in the fall of 1987 he finally worked up the nerve to walk into the storied Bitter End on Bleecker Street on a Monday night at one o’clock in the morning and get up onstage. Woody Allen and Bill Cosby had gotten their starts at the Bitter End, so he thought he would be in good company. Besides, the audience would be sparse at that hour, so he wouldn’t have to worry about getting heckled off the stage.