Another source of frustration was Reagan’s election during Stewart’s freshman year. “We always talked politics,” says Mike Flood, who played soccer with Stewart. “Neither of us was a particularly strong Reagan fan.”
Stewart scored 10 goals for William and Mary, but his hopes for a pro soccer career were dashed by injuries. “Toward the end of his career, he blew out his knee,” says his father. Still, Stewart’s legacy on The Tribe soccer team lives on in the form of the Leibo award, given annually in recognition of good humor and hard work.
After graduating from William and Mary in 1984, Stewart returned to New Jersey and kicked around at a number of odd jobs. He worked as a bartender at Lawrenceville’s Franklin Corner Tavern, sorted live mosquitoes for the New Jersey Department of Health and was a puppeteer for special needs schoolchildren. In 1986, he sold his car and moved to New York to try stand-up comedy.
“When he finally decided to become a comedian, it was a little bit of a shock,” Marian Leibowitz said in her Trenton Times interview. “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.”
In 1987, the young comedian known as Jon Leibowitz scored a gig at the Bitter End in the West Village—a comedy club where his idol, Woody Allen, had once performed. As he was being introduced, the emcee mangled the pronunciation of his name, prompting him to rename himself then and there, he told The New Yorker. But he also hinted at other reasons, such as “some leftover resentment at my family,” presumably referring to his strained relationship with his father.
The pronunciation of his name was not the only thing to go awry that first night at the Bitter End. Stewart made it only half-way through his act. “Legend has it that Jon bombed,” says Wendy Wall, who had booked him at the club. “But I really wouldn’t say he ‘bombed.’ It was one in the morning. It’s not easy with a crowd like that. It was obvious to me that he was funny.” Wall invited him back for a second night.
After becoming a regular at New York’s Comedy Cellar, he broke into television with an uncredited TV writing gig on Caroline’s Comedy Hour on the A&E network and in 1992 landed a spot as the host of MTV’s You Wrote It, You Watch It. Along the way he picked up a powerful fan, David Letterman, and became a frequent guest on Letterman’s Late Night on NBC, often sporting a tough-guy leather jacket. When Letterman decamped to CBS, Stewart was a contender to replace him as Late Night host but lost out to Conan O’Brien. Still, MTV liked him, and in 1993 tapped him to host his own talk show, The Jon Stewart Show, which quickly became the second-highest rated program on the network. The show lasted two seasons.
Stewart’s career slowly rolled on. He starred in Jon Stewart: Unleavened for HBO in 1996 and went on to score what are generally considered to have been mediocre guest-star appearances on sitcoms including Newsradio, Spin City and The Nanny, as well as roles in big-screen comedies like Adam Sandler’s Big Daddy. He was more successful playing “himself”—a young comic who is brought in to replace an older mentor—on the pseudo-realistic The Larry Sanders Show. In one episode, Stewart flouts the censors and airs a skit featuring a character dressed up as Hitler. The inspiration came from a rehearsal sketch for Stewart’s earlier talk show, in which Hitler tries to soften his image. “I don’t know what I was afraid of. These are delicious!” comedian Dave Attell’s Hitler proclaims after biting into a bagel.
Stewart’s studio audience had booed and the skit was shelved, but it later turned into a hilarious bit of back-story and the basis for an essay, “Adolf Hitler: The Larry King Interview,” in Stewart’s 1998 book, Naked Pictures of Famous People. In it, the former fuhrer accepts the blame for his past actions and psychoanalyzes why his plan for world domination failed. “What do I do? I deport or kill all my best scientists…. The Jews were some of my best technical people. It’s classic fear of success,” “Hitler” reasons.