The War for Late Night_ When Leno Went Early and Television Went Crazy - Bill Carter [59]
In 1999 Stewart accepted the anchor job on The Daily Show that Kilborn had abandoned—with just one week to prepare for his first appearance. It wasn’t network; it wasn’t after Letterman; it was even kind of sloppy seconds. But it was a nightly comedy show, with a bent toward news. Jon Stewart knew he was a news junkie, but more than anything else, he knew he was a comic.
Comic came after busboy, waiter, bartender, mosquito sorter, and construction worker, among other temporary roles. Jon Stewart was not preordained to be funny onstage the way Jay Leno had been as a boy in Boston. Stewart grew up in Lawrenceville, New Jersey, near Trenton. He was Jonathan Stuart Leibowitz then, second child of an elementary school teacher mother and physics professor father. The family broke up when Jon was nine, and later jokes left listeners with the impression that Jon did not easily forgive his father. (As late as 2002, Jon told interviewers that his father had never seen him perform.)
Jon was smart and athletic, ending up at William and Mary, where he played left wing on the soccer team. His only real entertainment background to that point was some horn playing in the high school band. At loose ends after graduation, he fell into a succession of odd—and odder—jobs, highlighted by one that made a real impression: as a puppeteer for children with disabilities. That tapped at least obliquely into the latent streak of humor submerged in Stewart, and the experience inspired him to set out to try stand-up.
It was a long and brutal initiation. Stewart spent close to a year working up the material—and courage—to appear at New York’s Bitter End club. When he finally did, he barely got through half the act before the flop sweat from the profound bombing he was delivering drove him from the stage—and almost out of the business. He stuck with it because at that point he wasn’t sure what else to do with his life.
For two years he worked during the day as a bartender at a Mexican restaurant in Manhattan, earning just enough to live on so that he could show up every night at the Comedy Cellar and go on as the last act. Every weeknight, somewhere near two a.m., Jon Stewart performed before the drunk and the lonely of the New York metropolitan area. “I sucked for two straight years,” Jon would later tell aspiring comics, partly as advice and partly as storm warning.
But slowly, incrementally, it came to him. Performing as Jon Stewart—he would later take the formal legal steps to abandon the name Leibowitz—he put on comedy muscle. His material got sharper, smarter. He landed some writing jobs, finally scoring a crucial gig hosting Comedy Central’s Short-Attention Span Theater. At around the same time, a young agent from William Morris, James Dixon, saw Jon performing stand-up. Sensing enormous appeal and potential in the obviously super-bright young comic, he signed him up. Much good—for both of them—would come from that initial connection.
Throughout the quick demise of his MTV and syndicated shows, his passage in and out of dalliance with the movies, and his unrequited affair with David Letterman’s production company, Stewart built his reputation with consistently impressive work. Everybody who worked with Jon came away thinking they had just encountered a driven, creative, and, yes, appropriately neurotic future star. All it would take was the right launch module.
The Daily Show was precisely the rocket he required. Stewart’s sensibility—and his insight that the show’s comedy should have a harder edge about the folly of both those in the news and the people in the media who were covering them—transformed TDS first to more smart than silly, and then from awfully smart to damn brilliant. By 2000 it was celebrated enough to start