Angry Optimist: The Life and Times of Jon Stewart

by Lisa Rogak

  He was wrong. “Everybody’s first song, first joke, is ‘This is who I am, this is where I was raised, this is who my parents are,’” he said.

  But first, the host botched “Leibowitz” during his introduction, which was a bit of a surprise in a city filled with seemingly unpronounceable names, Jewish and otherwise. It obviously didn’t help his nerves.

  So he took a deep breath and told his first joke on his firstever attempt at stand-up:

  “It’s lunchtime in the Diamond District,” he told a scattered crowd of drunks, tourists, and combative and competing comics. “All the stores close down and the street is filled with chasidim, who suddenly find themselves caught in Yidlock.”

  He was met with crickets before the heckling started.

  He gamely continued with more jokes in the same vein, about being Jewish in New York—though he had been warned by another club owner that this being New York, they didn’t need any more Jewish comedians—and approximately three minutes after he began, a guy in the audience yelled, “You suck!”

  “Jon went up on stage and bombed,” said Paul Colby, who owned the Bitter End. “I mean he bombed atomically. It was terrible to watch. By the time his set was over, Jon had had quite enough of show business. He said good-bye, vowing never to go near a stage again.”

  But Wendy Wall, Colby’s assistant, ran after him as he hightailed it out of the club, head down, face burning with shame. “I wouldn’t say he bombed,” she said. “It was one [A.M.]. It’s not easy with a crowd like that.”

  In any case, Wall saw something in Jon, a spark in between the Jewish jokes and the struggle not to visibly cringe at the heckling. She pulled him aside for a quiet talk and encouraged him. Part of him didn’t believe her, but a tiny part did. She actually made him promise her that he’d come back and give it another shot. Though it took him four months before he worked up the nerve to grace the stage again, he did, because despite the harassment and anxiety, telling jokes to an audience made him feel “better than anything else.”

  So he took the stage again at the Bitter End for another open mike—with Wendy Wall standing off to the side to encourage him—but before he gave the emcee his information for the introduction, he did something different.

  He changed his name. Instead of Jon Leibowitz, he became Jon Stewart, using his middle name as his surname, altering the spelling.

  “Most people assume I changed it because it was too Jewish, but I’ve never shrunk away from that. Half my act is devoted to being Jewish,” said Stewart. “It was something I needed to do. My folks got divorced. I was re-creating myself. It was a symbolic change. I was at a weird point in my life. At the time, I was really searching for a way to get away, to push a different path. I had lost my job, lost my girlfriend, and moved to New York on a lark. I have no regrets about it.”

  “The host’s hesitation at trying to pronounce my name that first night bothered me,” he said years later. At the same time, even though Jewish jokes would become part of his stock in trade over time, he didn’t want the joke to be on him. “You don’t want a tauntable handle in show business.” But even more than that, he admitted that some of the reason behind his decision to change his name came from “some leftover resentment at my family.” In other words, his father.

  Things went better for him the second time, and he quickly delved into new routines, polishing snappy comebacks to the hecklers, and more importantly, winning the respect of club owners around the city. While he continued to work at the Bitter End, he also started to appear at the Comedy Cellar, another notable stand-up club, where he soon took the last gig of the night five nights a week, which started at two in the morning.

  “I was the last guy [to go onstage] on weeknights,” he said. “I wasn’t good enough for weekends. But at 1:45 A.M., I went up there and did whatever popped into my head.”

  For his routines that first year he combined the subjects of religion, media, and politics and how he felt about them—similar to what he ended up doing with The Daily Show years later—but admittedly his material was much less polished and aware.

  “As I went on every night, I learned the difference between impersonating a comedian and being a comedian,” he said. “That was my break, learning how to be authentic, not to the audience, but to myself. I developed a baseline of confidence and also insecurity. I knew how bad I was, and I knew how good I was. And that is what helped me through a lot of the ups and downs as we went along.

  “It took me six years to write my first forty-five minutes,” he admitted.

  For the first year he spent in New York, he continued to work at a variety of menial jobs to pay the rent, but once he won the Comedy Cellar gig, he took a job with the City University of New York as a contracts administrator so that he could spend his evenings traveling from one club to another to check up on the competition and study their routines before heading to his own regular gig.

  And what competition it was. Ray Romano, Chris Rock, and Louis C.K. all started around the same time, along with Adam Sandler. For the most part, Stewart was at least a few years older than the rest of them.

  “I remember thinking at the time—and these were my exact thoughts—‘These young punks are going to have no trouble at all making it big, and that’s really annoying,’” he said. “You could just see success on Adam, even back then.”

  They began to hang out together, riffing off of each others’ hang-ups and visiting comedy clubs as a group. Stewart learned that they all shared the same traits: that while they weren’t the most optimistic people in the world, there was something about comedy that helped ease their pessimistic worldviews.

  “Most comedians are incredibly cynical,” said Stewart. “They do it to feed something in themselves. Somewhere in their brains a neuron fires happily and a need is eased, like a drug. It’s almost self-medication.”

  Most comedy clubs in New York paid either in “carfare,” ten or twenty bucks, or a meal. Stewart didn’t care. “I used to trudge around to four clubs a night, working for falafel money,” Stewart admitted.

  Stewart was fortunate in his timing: live comedy was becoming more popular at the time, and when he first started pursuing the life of a stand-up comic, demand was at an all-time high. New clubs were opening every week around the country, and restaurants and entertainment venues launched “comedy nights” on a regular basis. Open mikes in major cities like New York and Los Angeles were regularly scouted by talent agents and producers looking for the next best thing, and even in smaller regions, aspiring comics still held out hope that they could be discovered.

  “You could travel the country and make six hundred bucks, eight hundred bucks a week, or you could do what I was doing, which was open mikes for a plate of falafel.”

  He decided to stay in New York, work his day job, and play the clubs at night. Besides, he was still learning what material worked best.

  “The hope was just to get better, to learn what your voice was,” he said. “It was, in some respects, an exercise in Outward Bound for neurotics. It was a mental challenge. I honestly think it was a rhythm that I didn’t realize that I had. Until I got onstage, it didn’t actually make sense.”

  Because he had never performed in front of an audience before landing in New York, he learned in a trial-by-fire way that making your friends laugh is worlds away from making an audience of occasionally hostile, often drunk strangers laugh.

  But that’s taking the easy road to comedy.

  He also honed his ear. “In a weird sense, comedy is a lot like music to some extent,” he said. “You use your ear, you hear the flat notes, and do your best to try to avoid them. It’s an intuitive process, and your barometer is internal. And due to the volume of what we do, you hit a lot of flat notes, but it’s your gut that tells you what to proceed with.”

  He was thrilled at everything he was learning, and there was a part of doing stand-up that reminded him of being back behind the bar, serving drinks and holding court for his audienc
e.

  “When I first got into it, it was sort of like bronco riding: how long can I stay up here? But there’s an excitement of being uncensored and just speaking your mind. It’s one of the most exciting raw kind of forms of [performing] because you’re out there every night. In some ways, it’s gladiatorial.

  “You come to the realization that the special part is the moment of creation, and the rest of it is maintenance. When you take an act out and do it eight times in four days, you’re not gonna come up with much new stuff and it’s probably gonna become tiresome. Not only for you, but the waitstaff. You always hate it when the bartender is mouthing your punch lines. And not in a happy way.”

  He also learned that stand-up was different from one night to the next, and there was no use beating himself up over reacting to the extremes.

  At the same time, however, despite the encouragement he received from audience members, club owners, and other comedians, he constantly doubted himself and his abilities. His stress levels were through the roof.

  “It was a very anxious time,” he admitted. “It was really a matter of, ‘Who am I and what am I doing?’ I thought of stopping every day for the first four years.”

  “The first two years it was a constant battle,” he added. “I almost quit halfway through sets sometimes. It’s really frustrating. I mean until you get your legs, you don’t even know what you’re doing. Don’t forget, it’s not like you’re playing the Taj Mahal. It’s more like Uncle Fuckers Chuckle Hutch and everybody’s hammered.”

  “When he first started, Jon used to express a lack of confidence in himself,” said Noam Dworman, owner of the Comedy Cellar. “But then very quickly he became a very strong act. And then at some point he began to feel it was obvious he was heading for something bigger.”

  Stewart soon discovered that comedians with self-esteem far higher than his own quickly folded in the face of heckling and criticism. He began to see that the fact that he didn’t give up was just as important as honing his craft and studying the routines of others.

  “Basically you write jokes and those that work you keep doing and those that don’t, you throw out,” he said. “I wish I could say there was a magic formula, but I just kept working at it.”

  Stand-up veteran Chuck Nice agreed. “Perseverance is key, because you will get your chance in this business if you stick it out,” he said. “When I first started doing comedy, I ran into a famous comedian and asked, ‘What can you do to make it in this business?’ And he said, ‘Stay in the game, just stay in the game.’”

  Indeed, that’s exactly what happened for Stewart. A little over two years after he first took the stage at the Bitter End, Stewart was able to quit his day job and live off what he earned telling jokes to total strangers in front of a brick wall in a basement in Greenwich Village.

  Despite his success, his anxiety was never far from the surface. Once he had some experience under his belt, he auditioned at a club on the Upper East Side called the Comic Strip Live that was known for helping to launch the careers of Billy Crystal, Eddie Murphy, and Jerry Seinfeld. But the manager gave him a thumbs-down. “I was so gun-shy about it that I never went back there, even after it was working for me,” he said. “It was sort of like being a kid and being scared by a mop because you thought it was a monster, and now you have this weird thing about mopping.”

  Another time Stewart was booked for a show and he was sorely tempted to quit stand-up afterward. He was the opening act for musician Dave Mason at the South Street Seaport in lower Manhattan. “There must have been a thousand people there and halfway through the set, I realized that none of them were facing me,” he said. “Instead, they were all looking at this naked guy who was dancing around. At a concert that’s far more interesting than a guy talking about his grandmother.”

  Stewart decided to hit the comedy circuit on the road to test the waters and see how it compared with the New York comedy scene. He didn’t stay long. Not only did his Jewish shtick not travel well in some locales, but the lifestyle itself was less than desirable.

  “People don’t realize how fucking boring it is to go to a town outside Detroit from Tuesday to Sunday and stay in a Ramada Inn until seven o’clock at night,” he said. “I remember when I first went on the road. I’d go to a place like Lubbock, Texas, and ask, ‘What do you guys have, a prairie dog museum? I’m there.’ You explore every inch of that town, and by three years into it, you could be doing a gig in the Vatican and be like, ‘Nah, I’m not going out. I’m fucking staying in my room and drinking.’”

  In addition to staying in motels, comedy clubs would often put visiting comics up in apartments and condos solely for their use. “I’ve stayed in comedy condos that had huge holes in the walls because the last comic there didn’t have as pleasant a time as he’d expected,” he recalled.

  Stewart had become friends with another stand-up comedian, Lizz Winstead, and they shared the same dim view of constantly touring from one comedy club to the next. “Stand-up has become a giant nightmare,” she said. “The only comics who are working the road consistently are really blue and pretty low common denominator.”

  And so he settled back into Manhattan where one of his roommates turned out to be future (and now former) New York congressman Anthony Weiner. They hung out in the same circles when Weiner worked for another former New York congressman-turned-senator, Chuck Schumer. One of Weiner’s coworkers had played on Stewart’s soccer team at William & Mary, and Weiner had been dating another of Stewart’s roommates. Eventually Weiner moved into their Soho apartment and they also shared a beach house together. “It was a classic New York [situation],” said Weiner. “We were all making twenty grand. I was living there more or less because I was bumming off of my girlfriend who was living there.”

  As Stewart continued his stand-up career, it didn’t take long for TV to start calling. In 1989, he heard from a producer for Caroline’s Comedy Hour, a new show on the fledgling A&E network that basically broadcast stand-up routines from Carolines on Broadway. The comedy club by Caroline Hirsch had been launched in 1981 in New York and attracted top-tier comics from the very beginning, primarily because she paid them.

  “Carolines was different in that it was an actual job,” said comic Gilbert Gottfried.

  Though Stewart had previously performed onstage at Carolines, Hirsch had other ideas for him. Like Wendy Wall, Hirsch said she saw something different about Stewart from the very beginning. “It’s not easy, it takes a while, because you get to see that person and you think that person has a little something, but that doesn’t mean they all develop,” she said. “They have to work hard at it and morph.” She put him to work, after she moved the club to a bigger space at the South Street Seaport in downtown Manhattan, doing a children’s show, where a handful of comedians who regularly performed uptown did a show for kids. “Stewart was a Captain Crusader type, a superhero with a cape.”

  She also hired him for the new TV show. Stewart started as a writer for Caroline’s Comedy Hour, penning segues between stand-up segments as well as TV-friendly routines for some of the visiting comics. He also performed his own stand-up routines on a few occasions.

  He also began to work on a show called The Sweet Life on a small cable channel known as HBO’s Comedy Channel, which would later morph into Comedy Central. The variety show starred singer Rachel Sweet, who hosted a wide range of guests—famous and otherwise—in between comedy scenes and sketches. When that show went off the air after two years, Comedy Channel executives put him to work in front of the camera on a sketch-comedy show called Short Attention Span Theater, where he served as cohost with actress and comedienne Patty Rosborough. The premise of the show was simple: in between showing snippets from stand-up comic routines and films currently airing on HBO and Cinemax—which along with Comedy Channel were both owned by the Home Box Office parent corporation—Rosborough and Stewart would offer up commentary and jokes on the clips. Essentially, the show existed as a promotional vehicle.


  Stewart hosted the show for two years before MTV tapped him to serve at the helm of You Wrote It, You Watch It, a show where viewers would send in ideas for comedy sketches which would then be acted out by Stewart and a group of actors in an ensemble called The State.

  You Wrote It, You Watch It went on the air in 1992 but it lasted only thirteen weeks before MTV pulled the plug. As Stewart later described the show, “It was an odd cross between a reality-based show and a sketch show,” he said. “[When I was] offered the job, my agent said, ‘Take it. It’s stupid but it’ll be good for your career.’ I didn’t understand then, but she was right.”

  The sketches were pretty abysmal in their content, by Stewart’s own estimation, with topics ranging from passing gas to a woman who was laughing so hysterically that licorice inexplicably shot out of her nose.

  “You should see the ones we didn’t use,” said Stewart. “We got scads and scads of letters about people vomiting on animals.”

  After the show was mercifully put out of its misery, Stewart got the break he was dreaming of: he was booked to perform a stand-up routine on Late Night with David Letterman in March of 1993.

  “When I walked onstage, I blanked,” he said. “The audience is dark, and there’s just a little red light. [I] realize[d], it’ll be really quiet here if I don’t talk.

  “And afterward, my sit-down with Letterman was like an audience with the pope.”

  “It’s a great stepping-stone in the career of any comedian,” said Caroline Hirsch. “You get on there and do six minutes of stand-up and sit and talk with Dave, and you get asked back on again. And the more you’re on TV, the more you’re known and you become a bigger star.”