Jon Stewart Bill O'Reilly Debate Schedule and Preview: Why Stewart Will Crush O'Reilly

Bill O'Reilly Can't Possibly Win Against Jon Stewart.

Jon Stewart and Bill O'Reilly are holding a pay-per-view debate, “The Rumble in the Air-Conditioned Auditorium,” with half the proceeds going to charity. This is a no-win situation for O'Reilly, who has already lost just by agreeing to debate a comedian. Though Stewart and O'Reilly have tangled before, it was always as guests on each other's shows. The interviewer/interviewee dynamic is much different than the equal footing of a debate, and by engaging the host of The Daily Show, O'Reilly is inviting us to view his own show, The O'Reilly Factor in a similar fashion.

Despite the fact that Jon Stewart has become one of the most influential men in political discourse, he's still a comedian at heart. And while fans of The Daily Show certainly get plenty of laughs from The O'Reilly Factor, Bill O'Reilly is anything but a jokester. Debates are supposed to be a battle of equals, where truth is divined through rhetorical combat. In that sense, Stewart wins just by taking the stage next to arguably to the most respected pundit in the conservative camp.

Stewart's role as comedian also makes victory impossible for Bill O'Reilly because no matter how badly the conservative mouthpiece is winning, Stewart can always make the whole thing into a joke. There is no such easy out for O'Reilly, who has everything to lose and seemingly nothing to gain. Even if he argues circles around Stewart, a few clever quips from the funny-man are all it would take to make it seem like he has the upper hand. As long as Stewart can keep the tone of the evening from becoming too serious, the best O'Reilly can hope for is making a fool out of someone who earns their living as a clown.

The other aspect of this debate, which should be giving Bill O’Reilly second thoughts, is the location, George Washington University. It's no secret that college students love Jon Stewart, so he'll basically have home field advantage. This means that if things do start to go badly for Stewart, he can easily win the crowd while losing the argument and turn the tide of evening. On the other hand, putting Stewart in front of a group of humorless archconservatives would be like exposing Superman to kryptonite. The way it stands now, O'Reilly will be the one fighting an uphill battle right from the start.

Perhaps the face of Fox News has something up his sleeve, because I really don't see any scenario in which Bill O'Reilly comes out on top. At best, he'll force Stewart to make wisecracks rather than reasoned arguments, and at worst he'll have lost an intellectual duel to a comedian. I certainly wouldn't want to debate someone who gets paid millions of dollars to be witty.