Searching for Jon Stewart
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?"
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.
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
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.