Jack, Sheri and Oprah

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?"
Bridgette and Jason

Two hours before taping, Jack's co-producer Bridgette and associate producer Jason are trying to track down a tape Jon was supposed to leave at his hotel's concierge station. The tape isn't there—and no one is sure Jon's plane ever arrived. "Jon Stewart's flight last night was delayed because a miniature hurricane came through New York City," Bridgette says. "No one called to tell us that he didn't make his flight, but we don't have confirmation that he did either."

Finally, Bridgette and Jason make contact with his producer and find out he did indeed land in Chicago. Their next hurdle is determining whether Jon is actually en route to the show.

Jon Stewart

In his pre-show briefing with Oprah, Jack doesn't tell her Jon is missing. "In my head I'm thinking, 'OK, I hope he walks into the building in the next five minutes or we don't have a show,'" Jack says. "It's in God's hands."

Fifteen minutes to taping and Jon is nowhere to be found. "I'm in a full-blown panic," Jack says.

With five minutes to spare, Jon finally walks into the blue hallway. "I didn't know any of this was going on. In this stage of the game, 25 years in, all that stuff goes on truly behind the scenes," Oprah says. "And I'm really happy about it because in the early days I would be have been all in it."

The taping goes great—too great, in fact. Jon's appearance ran 18 minutes over schedule. "Jon was so funny I don't know what to cut out," Jack says. "This joke or this joke? It's like deciding between two of your children." 

See what made the cut

Watch Oprah and Jon discuss a possible Daily Show appearance after the show 


One day after the taping, Oprah figures out a way to make a Daily Show appearance sooner than later. Oprah calls Jon to offer to fly his entire audience to his Rally to Restore Sanity in Washington DC. "This is crazy what you're doing," Jon says. "It's such a lovely thing you're doing, it's very kind. It's unbelievable."

Watch Jon and Oprah plot the surprise. 

"And if there's ever anywhere that I can ever send your audiences, please," Jon says. "There are those little casino buses. I can send them over. It will be great."

Watch Oprah surprise The Daily Show audience 

Meanwhile, senior supervising producer Lisa and her team are scouting the perfect location for Oprah and Gayle to camp at Yosemite National Park. Check in on their progress.