Lisa Rogak - Angry Optimist

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.”