Lisa Rogak - Angry Optimist

“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 audience.

“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.