Free Jon Stewart: The Playboy Interview (50 Years of the Playboy Interview) by Playboy, Jon Stewart

Jon Stewart, March 2000

    Every evening, after the audience is locked and loaded but before taping begins, Jon Stewart bounds onto the set of The Daily Show to meet the people. He faces two sets of bleacher seats, cracks a few wry asides and takes questions from the crowd. Tonight a college student wants to know if Stewart will say the letters NYU on the show. Stewart mocks amazement.
    “Why? If I do it for you I’ll have to do it for everyone.”
    “Because I...I made a bet,” the kid stammers.
    Stewart is suddenly interested. “Oh? What’s the bet?”
    “I bet ten dollars. If you say it I win.”
    Stewart mulls this over. “Will you give me half?” he asks. The kid seems hesitant, so Stewart adds, “Come on. I can’t feed a family on cable money.”
    You can on the kind of cable money Stewart’s making: an estimated $1.5 million a year for four years as the new front man of The Daily Show with Jon Stewart , Comedy Central’s designated successor to Politically Incorrect . And according to the critics and fans, Stewart (who also helps write and guide the show) is worth every penny. Maybe that’s why, late last year, in a New York Observer column “memo to David Letterman” lamenting The Late Show ’s decline, Ron Rosenbaum wrote: “It started to go bad the moment your show stopped being about ridiculing big-ass, pompous television and started becoming big-ass, pompous television” and included an unexpected yet creative exit strategy: “Get Jon Stewart to replace you.”
    Not that Stewart is angling to move on. He has the greatest respect for Letterman, whose show helped launch Stewart’s career, positioning him to have a talk show on MTV and, later, in syndication. And then there was the deal with Letterman’s production company to host either a 1:30 A.M. talk show or to replace veteran Tom Snyder, for whom Stewart served as guest host, on The Late Late Show With Tom Snyder .
    Are you keeping this all straight?
    Stewart is a bright talent whose lightning-fast prowess with the ad-lib and wisecrack is savant-like. Since taking over The Daily Show from Craig Kilborn, he’s seen the show’s ratings improve (while Kilborn, who took over the Snyder show, seems badly miscast in his new role). Critics have raved about Stewart’s self-effacing charm and smartass sensibility. That sensibility has been the secret to Stewart’s success dating back to his days as talk show host on MTV. He doesn’t try to be hip in the slightest, and yet he comes across as the hippest comic on television. It’s no wonder that one critic called The Daily Show “the smartest thing on the air.”
    Jonathan Stewart Liebowitz, 37, grew up in the Trenton, New Jersey suburb of Lawrenceville, where he lived with his father, Donald, a physicist for RCA, and his mother, Marian, an educational consultant. The couple divorced in 1971, but otherwise Stewart’s wonder years were typical for a young Jewish boy. He wondered: Would he “grow taller, get better looking, get laid”? Meanwhile, Stewart took refuge in Mad magazine, The National Lampoon and the defensive use of comedy to short-circuit any comments about his height, looks or religion.
    At the College of William and Mary he got the answers to his questions (yes, yes and yes) and graduated with a B.S. in psychology, which he promptly put to use working as a bartender. His best drink: “A Whack in the Head—a mixture of Alabama Slammer and Long Island Iced Tea. Drink two and you’re not getting up the stairs.”
    Stewart also worked for the state of New Jersey in various civic capacities and eased into a comfortable middle-class lifestyle that left him uncomfortable.
    In 1987 he decided to pack his bag for New York City and test his secret ambition to do stand-up. His coming-of-age at the famed Bitter End was less than auspicious, but it still made him feel “better than anything else” he’d done. Even when another club owner told him that there were already too many Jewish