STEW BAILEY: Carell and Nick McKinney, the producer, had pulled the question out of Time on the way there, driving to the shoot. Just the fact that Steve Carell can get those words out of his mouth and that it sounded like something a smart person would say really threw McCain off. There was such a delay.

STEVE CARELL: It was really funny because all of McCain’s handlers . . . you could feel the whole bus tense up. I thought McCain might just laugh it off, or probably give me some sort of joke response.

BEN KARLIN: I remember seeing it in the editing room. I remember Jon called me down, and seeing it and thinking, Yeah, this is what we should be doing. This is the goal. It was one of Carell’s most incredible moments. He asks McCain a question in a way that no journalists were talking to the candidates. And it was like, Oh shit, we are able, in this weird, unintentional way, to add a level of insight to the process that doesn’t exist. That was really, really exciting. It meets the standard of being funny; it meets the standard of being relevant.

JOHN McCAIN (U.S. senator, Arizona, 1987-; Republican presidential nominee, 2008):

That was great. I still remember Steve Carell on the bus. I was certainly aware of Jon and the show early on, and knew they would try to have some fun with us. I wanted to be funny. I wanted these young people to know that I’m a guy with a sense of humor. I’m not some dull, dry, old senator.

BEN KARLIN: That moment, it was the beauty and the weakness of The Daily Show. You had this incredibly pregnant moment where you forced a politician to go off-book, and it was uncomfortable, and it was honest. Then, because of our role as a comedy show, you have to take the air out of it, and it let McCain off the hook.

STEVE CARELL: Yeah, to press it—we really hadn’t set ourselves up in that context to start going after him. It was making fun of a gotcha moment. And I think that a lot of what we do on The Daily Show is making fun of journalistic tropes, and I think that was one of them.

MO ROCCA: That was the first time we were in The New York Times—in a news-analysis piece, not the TV column.

JON STEWART: The real revelation for the show, covering the 2000 campaign, was that before everything that happens publicly in politics there’s a meeting—so what’s that meeting? That’s what’s interesting. It always struck me as “We’re always covering the wrong thing. We’re always covering the appearance, but we’re never covering that meeting.” When you watch that pack of cameras follow a presidential candidate, you go, “That’s not interesting. What’s interesting is to stand behind them and watch that,” because then you learn a little bit about the process.

That’s when the idea of deconstructing the process came to the fore of how we were going to make the show. Before, it was just . . . we were making jokes. Some of them were insightful; some of them were not. The show came to exist in the space between what they’re telling you in public and the meeting that they had where they decided to do it that way. Seeing that was the aha of “That’s the show.”

CINDY McCAIN: I still have those jackets, by the way. I talked them out of their big New Hampshire jackets. They were around John so much, and I finally said, “Look, these jackets are too good. I’ve got to get one from you, please.” They gave them to me. It’s a great souvenir.

Adapted from The Daily Show (The Book): An Oral History as Told by Jon Stewart, the Correspondents, Staff and Guests, by Chris Smith, with a foreword by Jon Stewart, to be published this month by Grand Central Publishing; © 2016 by Busboy Productions.