Hosting the Oscars
Jon Stewart's biting humor often sinks its teeth into someone or something — the government, the Tea Party or the banks — and that's just what he did when he hosted the 2008 Academy Awards. He made fun of Scientology, told Hollywood it was too liberal, and asked viewers at home to stop pirating movies because these wealthy, successful celebrities were "the people you're stealing from."
Hollywood likes to laugh at itself only when it gets to dictate the terms, and as an Oscar host Stewart received mixed reviews. Luckily, he didn't seem to mind. "You're either a guy hosting a party for your friends, or a guy watching a party you were invited to," he told the New York Times before the ceremony. "I'm much more in that category. I embrace that."