In the first few weeks of Season 25, producer Jack has revisited Williamson, West Virginia's landmark AIDS town hall and welcomed living legend Liza Minnelli. His next assignment? Funnyman Jon Stewart. "Jon Stewart may be one of the all-time great Oprah guests because he understands television. He understands timing. He understands how to say something poignant, direct and funny in a short amount of time," Oprah says. "He knows it's a dance. He understands the dance and he comes to play."

When Jack meets with Oprah, he pitches the idea of Jon turning the tables on Oprah with his own questions. "He's like, 'I'm never going to have Oprah on my show. It's the 25th season. It's my last chance,'" Jack says.

Oprah says she would love to be a guest on The Daily Show. "Has he ever invited me on his show?" she says.

After confirming with Harpo's public relations department, Oprah finds out The Daily Show has never asked her to appear. Oprah then tells Jack she's got a comeback ready if Jon wants to break out his questions: "Do you want to waste these questions here?"