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Scoring the 5 best Jon Stewart vs. Bill O’Reilly showdowns


In honor of Jon Stewart's final "Daily Show" episode airing Thursday night, his  TV nemesis Bill O'Reilly was asked to write a letter of appreciation -- a sort of exit interview of what it was like to spend 15 years feverishly arguing with Stewart and serving as the butt of hundreds of Stewart's jokes and biting satire.

O'Reilly was happy to kick Stewart out the door with a few insults:

"Jon Stewart is being held captive by a self-imposed left wing view of society. ... I’m sure he would reply with a sardonic put down of my audience as out of touch white people, but then again most folks who watch me actually held a job at some point."

But the Fox News host also had some semi-kind words to say about debating Stewart, which the two did on each other's shows frequently:

"Stewart actually thinks about things from time to time," O'Reilly said. "He’s good at spotting phonies and is quick with a quip when challenged."

We decided to look back at some of these polarizing figures' most pitched debates and, in the nature with which they were fought, score them using our own totally subjective criteria.

Let the games begin.

Round 1: Does Fox News feed on fear?

An unexpected, headline-grabbing debate between the two TV show hosts raged in 2010 when O'Reilly hosted Stewart on his show and the conversation turned toward Stewart's criticism of Fox.

O'Reilly asked Stewart why he thought Fox News was rated by a then-recent poll the most trusted news channel among Americans. Stewart replied that Fox News has won viewers through succinct and clever messaging that borders on panic.

"Here’s what Fox has done, through their cyclonic perpetual emotion machine that is a 24 hours a day, 7 days a week," Stewart said, "they’ve taken reasonable concerns about this president and this economy and turned it into a full-fledged panic attack about the next coming of Chairman Mao."

The bottom line: Though a video wasn't available, it appears from media coverage and our collective memory at The Fix that Stewart out-foxed O'Reilly on his own show. Round one goes to Stewart.

Round 2: The rapper Common

In 2011, Stewart came on to O'Reilly's show to debate whether the rapper Common, who wrote a song about a woman who killed a state trooper, should have been invited to the White House.

"The president of the United States takes him into the house, thereby validating him," O'Reilly said.

Stewart points out that Bono wrote a song about Leonard Peltier, convicted of killing two FBI agents. "Guess where he was? The White House. Booya! (That's a rap word.)," Stewart replied, adding that Bob Dylan also wrote a song about a convicted killer. "Why are you drawing the line at Common? There is a selective outrage machine at Fox."

O'Reilly says the line is drawn because Common came to visit the president.

"It's a poetry slam. Who gives a crap?" Stewart retorted.

The bottom line: O'Reilly won this for tenacity.

Round 3: Is Jon Stewart hopelessly liberal?

In that same May 2011 show, all O'Reilly wanted from Stewart was to prove that the "Daily Show" host was/is biased.

"You really didn't know much about me do you?" Stewart replied.

"And I don't want to," O'Reilly retorted. He added: "Was there ever a scenario where you could see not voting for Barack Obama and voting for a Republican?"

"Sure," Stewart replied, maintaining he's open-minded.

Then O'Reilly asked point-blank: "Has [Barack Obama] lived up to your expectations?"


"No," Stewart said, adding that he doesn't "necessarily agree with" how the president sometimes engages with Americans and Congress.

The bottom line: O'Reilly couldn't prove what he set out to prove, but he got what he wanted out of the debate: A headline that "Jon Stewart says Obama hasn't lived up to his expectations." O'Reilly won this one.

Round 4: The 2012 'Rumble'

In the heat of the 2012 presidential campaign, O'Reilly and Stewart put on a debate of their own: The live-streamed "Rumble in the Air-Conditioned Auditorium" in Washington, D.C.

The debate was good TV -- the 5-foot-7-inch Stewart at times used a mechanical riser to elevate himself to match the 6-foot-4 O'Reilly. At one time, Stewart climbed into O'Reilly's "yeti-like" lap.

The bottom line: Press from the Rumble was pretty clear: It was a draw -- or a win for either man, based on how you define the desired outcome. Time's Katy Steinmetz:

"If the debate were scored on points well made, Stewart would have taken home the gold. He used a larger range — from dropping F-bombs to waxing poetic about the greatness of the U.S. — to outfox O’Reilly’s classic news-show style."
"But from a p.r. perspective, O’Reilly was the real winner. His willingness to engage and be ridiculous with Stewart serves as proof that the employees at Fox News aren’t all humorless conservative zombies, as Stewart and other liberals often paint them."

We'll go with the conventional wisdom on this and call it a draw.

Round 5: White privilege

In this 2014 debate on "The Daily Show," all Stewart wants is to hear O'Reilly say that white privilege exists.

That, of course, didn't happen. The eight-minute debate turned into an almost-shouting match. Stewart argued white people set the system; O'Reilly argued there was once was a thing called white privilege, but no longer.

"Maybe you haven't figured out that there is no more slavery, there is no Jim Crow," O'Reilly said. "And the most powerful man in the world is a black American, and the most powerful woman in the world, Oprah Winfrey, is black."

O'Reilly agreed that systemic problems exist for every race, but not at the extent Stewart was arguing.

The bottom line: Stewart clearly had the upper hand this debate, but then again, it was his show. He also never got O'Reilly to acknowledge whether white privilege exists, though O'Reilly did concede that as a race, black Americans "are carrying more of a burden" than white Americans. Stewart won this one.

So, if you were keeping track, that's a 2-2-1 tie. Of course, you could also say that the two men co-existed as near-perfect foils for one another, helping each gain favor with his given audience. In a way, both men are very clearly winners when it comes to this feud.

And because he so often grants it to his guests, we'll have O'Reilly have the last word:

"Stewart sincerely believes that most African-Americans are still being victimized because of their skin color. I put forth that organized bias has vanished in this country although individual prejudice remains a part of the human condition and will always be there. Stewart made his points, I made mine. At the end of the discussion we had a few laughs as we always do."