Bill O'Reilly vs. Jon Stewart: 10 Best Moments From Their Online Debate

Jon Stewart Bill O'Reilly Debate - H 2012

The "Daily Show" host and Fox News icon clash on healthcare and foreign policy, but also talk Clint Eastwood for President and what it would be like to trade jobs for a week.

Basic cable frenemies Bill O’Reilly and Jon Stewart squared off Saturday night in a debate streamed online from George Washington University. Dubbed “The Rumble in the Air-Conditioned Auditorium,” the Fox News Channel and Comedy Central personalities tackled the issues—and each other—with a back and forth that was refreshingly rude compared to the staid politeness expected of presidential candidates.

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The debate included O'Reilly jokingly naming Clint Eastwood as the famous person he’d pick for U.S. President. Stewart responded by getting out of his chair and addressing its seat cushions. “Why don’t we ask him?” Stewart said, creating an “invisible Eastwood” in mockery of the actor’s Republican National Convention speech.

The debate was streamed online for $4.95, with half the proceeds going to charity. But the event, moderated by CNN and Fox veteran Ed Hill, proved too popular for its own good, as untold numbers of people were unable to stream it until halfway through the show. Complaints flooded into the Rumble 2012 Facebook page, which prompted organizers to post an apology, stating its servers were overloaded.

Below are 10 highlights from the O’Reilly vs. Stewart debate.

1. O’Reilly comes prepared—with signs.

The O’Reilly Factor host is famous for the “Talking Points Memo” section of his TV show. Without the use of TV graphics to illustrate his points, O’Reilly came armed with a series of signs, including some that read: "Bush Is Gone" (to emphasize President George W. Bush can’t be blamed for our current problems); “Iran not frightened” (to argue President Obama’s foreign policy does not sufficiently keep Iran in line); “Drones Yes, Waterboards No” (to point out the irony of it being chic to condemn water boarding but not to be outraged over bombings.)

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2. Stewart calls O’Reilly Mayor of "Bullshit Mountain."

In a Daily Show episode last month, Stewart dubbed Fox News “Bullshit Mountain” for its response to Mitt Romney’s now infamous 47 percent hidden camera video. In the debate’s opening minutes, Stewart said he had come to plead with “the mayor of Bullshit Mountain” to talk some sense into his people (presumably Fox viewers and employees).

Shortly before, Stewart said his friend O’Reilly was “completely full of shit.”

3. Stewart helps O’Reilly make hip references.

After O’Reilly argued foreign aid is needed to “buy” friends in hot spots around the world, he said he didn’t’ care if “Gerry and the Pacemakers” attacked a U.S. Embassy, Egypt could have stopped it.

Stewart rejoined that their debate was being broadcast online, and Gerry and the Pacemakers wasn’t a reference the audience would likely get.  O’Reilly revised his statement, saying it didn’t matter if  “Lil' Wayne attacked” our embassy.

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4. Stewart freaks out when O’Reilly says the Iraq War shouldn't have happened.

The men were asked whether military or volunteer service should be mandatory. Stewart said “There should be a draft,” but “not necessarily for the military.” His would include the option for volunteer service.

O’Reilly said he was against the draft, period, and went on to muse about recent U.S. wars: “We should not have gone to Iraq. Afghanistan we had to.”

Stewart stood on his chair and yelled “Live tweet that:  Bill O’Reilly said we should not have gone into Iraq.”

5. O’Reilly reveals which famous person he would save.

Asked “Which famous person would you save if the U.S. were burning?”, O’Reilly gamely answered “Oprah—she’s worth about $100 billion.” A bemused Stewart said “My family…. listen, Oprah’s a great answer too.”

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6. Stewart calls O’Reilly’s electoral plan “Chutes and Ladders.”

When asked how he would change U.S. democracy, O'Reilly pitched a plan he described as a “more participatory democracy,” in which only those who had voted in the previous election could vote in the next one.

“If you sat it out one time, then you’d miss a round” O’Reilly said.

“Yeah, let’s do it like a game of Chutes and Ladders,” Stewart said, mockingly.

O’Reilly explained he simply wanted people to become “more involved.”

“Fifty percent of people know nothing,” about government O’Reilly said. “The Jersey Shore people…the Colbert watchers.”

Stewart rejoined: “Yeah, not everyone’s as bright as a Fox viewer."

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7. Stewart picks O’Reilly’s “silliest” statement of the evening.

While sparring over whether government should run the healthcare system, O’Reilly said one need look no further than Great Britain for why government run healthcare doesn’t work. “In Britain, everyone’s teeth have fallen out,” he joked.

O’Reilly argued government was good at running things such as the military and the tax system, because it had a “tradition” of doing so—while it had no such tradition with healthcare.

That may be the silliest thing you've said all night,” Stewart said, before arguing government could make healthcare part of a proud tradition, just as the military is.

8. Stewart sits on O’Reilly’s lap.

Stewart and O’Reilly were asked how it was possible two opposing personalities such as themselves could sit down to hash out ideas, yet Congress could not do the same. Did they have any advise for the divided Congress?

Stewart climbed onto O’Reilly’s lap, and the men sat there uncomfortably for several moments.

“And what would you like for Christmas, little boy?” O’Reilly asked, before throwing Stewart off. (They moved on without answering the question.)

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9. O’Reilly reveals why he could never host The Daily Show.

Asked if they could switch jobs for a week, O’Reilly said  “Are you kidding? I’d have to work in the same building as Colbert?”  Stewart said visiting the Fox News building was fun, because the Eye of Sauron was on top of it. He also noted Fox employees resembled the slave children from Indiana Jones and the Temple of Doom.

“The only way I’d do it is if someone kicked me hard in the nuts,” Stewart concluded.

10. Stewart and O’Reilly show each other some love.

So…what do the two men admire about each other? Stewart joked O’Reilly “coordinates a mean outfit," He then got serious, adding “Bill comes by his principles honestly. He’s a smart guy. He’s a funny guy…this idea that disagreeing with somebody…means you should not engage them is ridiculous.”

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O’Reilly kept it short, joking he admired a man who could complete rehab six times and still become as successful as Stewart. 

He added “Stewart tomorrow is going to visit the wounded troops.”  O’Reilly let that sink in with the crowd, which responded with big applause.