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

comedians, Stewart didn’t retreat to suburbia. He got a job hosting Short Attention Span Theater on Comedy Central in 1991. In 1993 he tried out with every other comedian to succeed Letterman on Late Night ; Conan O’Brien got the job. Eventually, Stewart appeared on an HBO Young Comedians Special , then did the Late Show With David Letterman . That shot got MTV interested and he signed on to host the half-hour Jon Stewart Show , which debuted in September 1993. Paramount expanded the format to an hour and syndicated the show. Soon it was being replaced by Roseanne reruns, shifted to the 3:30 A.M. slot and was canceled in June 1995.
    During the next few years Stewart turned up in unexpected places, including The Larry Sanders Show , where he often appeared as himself and was a creative consultant. He also launched a movie career ( Half Baked, Playing by Heart, The Faculty, Big Daddy ), hatched a production deal with Miramax Films and wrote a humor book titled Naked Pictures of Famous People . Rather than rely on the stand-up material he’d already mined in his 1996 HBO Comedy special, Jon Stewart: Unleavened , Stewart wrote essays skewering the conceits of popular culture. It was an immediate New York Times best-seller.
    In January 1999, Stewart replaced the host of The Daily Show and hasn’t looked back. “I’m very happy now,” he says. Even if it doesn’t get any better than The Daily Show ? Yes, Stewart insists. “Let’s just say that if it never gets any worse than this, then I’ve had one of the luckiest runs ever.”
    We asked Contributing Editor David Rensin , who last interviewed David Spade for us, to spend a few days with Stewart on the set of The Daily Show . Rensin reports:
    “His office is littered with the detritus of celebrity: unopened champagne bottles, promo items, gift baskets and a biohazard container left by ‘a guy who did flu shots. I wanted something to remember him by.’ Jon’s mind is similarly littered, but with the raw material of comedy-to-order. He could send up any topic instantly, especially when he detected an intentional (or unintentional) set-up in my questions.
    “For our second meeting, he asked if we could talk during the sixth New York Mets—Atlanta Braves playoff game. We ordered in pizza and Cokes. ‘This is going to be the best 12-year-old’s pizza party you’ve ever had in your life,’ Jon said. It was touch-and-go the whole game, and we would have watched the entire thing, but Jon kept calling his girlfriend to rave every time the Mets scored. Eventually he decided to catch the last few innings with her, and we said goodnight.
    “The Mets lost, so I wanted to begin our next conversation on a cheery note.”

    Playboy: Congratulations.
    Stewart: Thanks. [ pauses ] For what?
    Playboy: Isn’t The Daily Show the longest you’ve ever held a job?
    Stewart: That’s true. I started January 11, 1999. How did you know?
    Playboy: This is Playboy. We know everything.
    Stewart: We’ll see.
    Playboy: Tell us about the time you destroyed thousands of dollars’ worth of aquariums in what can loosely be described as a gymnastics accident.
    Stewart: You do know. [ smiles ] First, the tanks were empty. No fish were harmed in that senseless tragedy. It was 1976 or 1977. My brother was an assistant manager at one of the first mega Woolworths. He was a bit of a taskmaster, but good people. The main floor was filled with entertaining and wonderful items. I worked downstairs in the catacombs, with the stock shelves. To alleviate some of the boredom, we used to dive off the shelves. They were pretty high, but it was OK because this was back in the day of the beanbag chair. We’d pile them up and do whatever gymnastics routine we could imagine. Unfortunately, I hit a bag wrong and it shot across the room and wiped out thousands of dollars’ worth of aquariums. Fortunately, I had the key to the incinerator. But, much to my chagrin, aquariums make a lot of noise when they burn. It