When Jon Stewart and Bill O’Reilly take the stage at George Washington University’s Lisner Auditorium on Saturday night to engage in a political debate tabbed The Rumble in the Air-Conditioned Auditorium, their most partisan fans might be craving blood. After all, O’Reilly is Fox News’ looming, scowling conservative he-man, and Stewart is more than paying for his kids’ college education by routinely mocking Fox News’ style and substance four nights a week on The Daily Show. But as anyone who’s watched the adversaries joust on each other’s shows over the years, their relationship is anything but bitter. It’s more Oscar & Felix than Hamilton & Jefferson or Ali & Frazier, though Stewart suggests it’s even deeper than that. “I think it’s more Hepburn and Tracy,” says the comedian. “I think there’s a lot of sexual tension under there. Who’s who? It switches. It depends.”
The two TV giants have taken turns appearing on each other’s programs, bravely venturing into “enemy territory” to promote their respective best-selling books and challenge each others’ worldviews. Their political differences, however, have failed to undermine an undeniable fondness, if not sincere respect for each other. “I like Stewart,” says O’Reilly, whose show has now been the top cable news program for 50 straight quarters. “He’s a smart guy, and he’s always fun to joust with. He always comes up with some interesting things. I challenge him, he challenges me.”
That Stewart has a soft spot for O’Reilly is clear in the way he covers The O’Reilly Factor, as opposed to his contemptuous treatment of ex-Fox News superstar Glenn Beck and the trio that hosts the Fox & Friends morning show. When Stewart pokes O’Reilly, there always seems to be an accompanying wink that says, “No hard feelings, I’m just keepin’ ya honest.” “He reminds me of everyone that I used to bartend for,” says Stewart, whose show just collected its 10th straight Emmy. “You know, down in the basement bar of a liquor store at a place called the Bottom Half, and everybody would have their Ayatollah Assahola shirts, and we’d all just be sitting there drinking beer. It’s the neighborhood, the syntax, the rhythm, it’s all very familiar to me.”
So when O’Reilly decided over the summer that there might be an opportunity to raise some money for charity, there was only one liberal personality who could deliver the goods and go toe-to-toe with him in a debate. He rang Stewart and made his pitch. “By reached out, I mean he literally he called up and said, ‘Stewart. Debate. October. Let’s do this,'” says Stewart, in his low-voiced imitation of O’Reilly’s bark.
“There wasn’t a lot of back and forth,” says O’Reilly. “He and I are pretty much on the same page as far as presentation and how to do things. It was fairly seamless. We had one meeting after that, and just hashed it out.”