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Whenever Bill O'Reilly appears on The Daily Show or Jon Stewart stops by The O'Reilly Factor (which he'll do tonight to plug his new film Rosewater), it makes news. Predictably, O'Reilly and Stewart's most recent meeting generated the kind of sensational headlines that keep bloggers fed. Mediate went with, "Stewart vs. O'Reilly Showdown: Intense Battle Over White Privilege." The Blaze headline read, "Debate Over 'White Privilege' Between Jon Stewart and Billy O'Reilly Descends Into Shouting Match." Headlines like these drive pageviews, training viewers to expect a fierce battle between two partisans. Headlines like these are also deeply misleading.
The relationship between Bill O'Reilly and Jon Stewart is far more nuanced than these headlines would have you believe. Sure, the two men are on opposite poles when it comes to the issues, and they do raise their voices at each other from time to time. If you watch the exchanges that the two men have had over the past decade, however, there is far less hostility than you would think. Though both men are always game for a debate, their conversations are filled with more jokes, friendly jabs, and signs of mutual respect than anger. They joke about exchanging emails and gifts; they promote each other's projects; they come together on some fundamental issues.
A look at the history of O'Reilly and Stewart's relationship reveals men who put their admiration for each other above their partisan differences. Though these two are sometimes so far apart that one man's views can utterly confound the other, they respect each other as men unafraid to speak truth to power.Here is a history of Bill O’Reilly and Jon Stewart’s frenemy relationship.
Brenden Gallagher is a contributing writer. He tweets here.
The Beginning
Date: Jan. 22, 2001
Show: The Daily Show
Most uncomfortable moment: Stewart wonders aloud if he'll have a job in four years.
O'Reilly and Stewart bonded from the very beginning. In this interview, less than two years after Stewart took over The Daily Show, they came together on an issue that has united many Americans through the years: criticism of George W. Bush. O'Reilly spent most of the interview describing how he shook Bush out of his comfort zone by challenging his policies on his show. He then went on to explain to a then green Stewart how he approaches journalism.
It is so strange to watch O'Reilly and Stewart all those years ago. Back in 2001, O'Reilly was an unabashed supporter of FOX News; he had the swagger of a man backed completely by the conservative media establishment. Those were the days when he was a rating juggernaut, and he carried himself like he was coated in Teflon. Stewart showed flashes of idealism that you can't find any traces of after over a decade more covering the news. They were a bit cautious around each other during those first meetings, but over the next decade they would both grow more visibly cynical and more fond of each other.
News vs. Comedy
Date: Sept. 17, 2004
Show: The O'Reilly Factor
Most uncomfortable moment: "You asked me why I'm such a bad person. Is that serious question?" —O'Reilly, referencing his Daily Show appearance
Just a few years after O'Reilly stopped by the The Daily Show to discuss his approach to political journalism, Stewart stopped by The O'Reilly Factor to explain how he isn't a political journalist. "We're not competitors in terms of content. You're a news show and we are a comedy show." he said. Stewart has fallen back on this refrain a number of times over the years, and to O'Reilly's credit, Bill tries to hold Jon's fee to the fire. "What do you want the audience to get out of your discussion with Kerry? Yucks or anything else?" he asked Stewart. While many conservative pundits were, and still are, quick to accept Stewart's self-proclaimed position of court jester, O'Reilly saw early on that Stewart was at the helm of something far more than important than just a comedy show.
A.C.: After Colbert
Date: Oct. 18, 2005
Show: The Daily Show
Most uncomfortable moment: The audience boos O'Reilly after he says, "We're boycotting France."
One of the most interesting meetings between Bill and Jon came the day after The Colbert Report premiered. The debut of Colbert's show, a clear parody of The O'Reilly Factor, left O'Reilly in a reflective mood. He admitted to being worn down, and lamented, "I have to bring every night to the table a sense of outrage." This led to a frank conversation about why O'Reilly does what he does and how much it wears on him. Though the two had been friendly before, this interview marked the beginning of a kind of candor in the conversations between O'Reilly and Stewart, a mutual understanding of the performance aspects of their work, that would color their relationship from that point forward.
Fear and Loathing in the Obama Administration
Date: Nov. 13, 2008
Show: The Daily Show
Most Uncomfortable Moment: "If you go to Alabama, you're going to be killed." —O'Reilly, on the "center-right" majority of America
It's hard to blame Stewart for gloating during his interview with O'Reilly two short weeks after Obama won the Presidency. Bill plays right into Stewart's hand shortly into the interview. O'Reilly tells Stewart how fearful he is about Obama's Presidency, and Jon is ready with hot cocoa and a stuffed animal to help mollify O'Reilly.
After Bill takes his ribbing with good humor, they get into the nature of the American electorate. O'Reilly argues that America is really a "center-right" country, out of step with Obama's policies. Stewart asserts that Americans are more closely aligned with Obama. O'Reilly responds by predicting a backlash from Middle America in response to Obama's more liberal policies. Six years later, it looks like we have to give points to Bill on this one.
UnCommon Tension
Date: May 16, 2011
Show: The O'Reilly Factor
Most uncomfortable moment: "Stop attacking the Weather Girls. They're one of my favorite groups." (O'Reilly, in reference for his love for the group behind the song "It's Raining Men.")
Though O'Reilly and Stewart are usually able to put their differences aside, sometimes they are so passionate about the issue at hand that real anger and frustration comes through in their playful jabs. This was the case when Stewart came on The O'Reilly Factor to discuss Common's visit to the White House. The substance of the conversation can be boiled down the Stewart's words to Bill early on in the segment, "Correct me if I'm wrong. If an artist supports someone convicted of killing a cop, they should not be allowed to visit the White House."
For O'Reilly, this issue is about respect for law enforcement and the sanctity of a White House visit. To him, Common is a radical, agitator, and supporter of domestic terrorism that shouldn't be anywhere near the White House. For Stewart, the conservative outrage over Common's visit is an ugly combination of racial politics and censorship. This argument reached it's hottest point when Stewart said to O'Reilly, "Guess who wrote a song about Leonard Peltier? Bono. Guess who visited the White House? Bono. Bob Dylan wrote a song about Hurricane Carter. There is a selective outrage machine here at Fox News."
In this segment, O'Reilly and Stewart hit each other's most sensitive points, resulting in one of their most hostile exchanges to date. This marked one of those rare instances where their disparate ideologies trumped their mutual understanding.
Taxation and Misrepresentation
Date: Sept. 28, 2011
Show: The Daily Show
Most uncomfortable moment: "See, you don't even know what the $16 muffin is!" —O'Reilly on government waste
"You say if Obama raises your taxes to 50% that you may not do your show anymore. What percentage of that threat is empty?"
"All of it."
On this occasion, the pundits kept it light because they knew they were treading familiar territory. The topic of discussion was taxation; specifically, how much should be paid, and how large the government should be. O'Reilly came armed with examples of government waste. Stewart retorted with the ways government has had a positive impact on our lives and how private enterprise is often more guilty of waste when they fill the void left by small government.
Only once did O'Reilly fall into the traditional conservative racially tinged, classist comments. O'Reilly said, "We have a trillion dollars in the underground economy." He then went on to complain about inner city drug dealers who aren't paying taxes on their Bentleys. Confused, and eager to get back to the discussion at hand, Stewart said, "In you mind, the debt crisis in this country is caused by renegade cocaine dealers?" Luckily for all of us watching, they quickly got back to more reasonable points on economic policy.
The Debate Promo
Date: Sept. 18, 2012
Show: The O'Reilly Factor
Most uncomfortable moment: O'Reilly: "Dating Game is going to be on PBS now." Stewart: "What did these nuns do to you?"
During the run-up to the O'Reilly-Stewart debate in the fall of 2012, the "Rumble in the Air Conditioned Auditorium," Jon joined Bill on The O'Reilly Factor. They opted for a wide-ranging, loose discourse rather than a focused policy discussion. O'Reilly asked Stewart why he wants to debate him, and Stewart made a Star Wars analogy: "The reason I'm doing this, Bill is very similar to Luke Skywalker and Darth Vader. As he told Yoda or Obi-Wan Kenobi, I sense there is still good in you."
From there they discussed their experiences in the year's political conventions, Southern hospitality, Sandra Fluke, and Clint Eastwood in a segment that had more the flavor of shooting the shit over a beer than prepping for a debate.
The Great Debate
Date: Oct. 6, 2012
Show: Special event
Most uncomfortable moment: In response to being asked what American they would save from a fire:
O'Reilly: "Oprah."
Stewart: "My family. But Oprah's a good answer too."
We can only dream of bringing the level of civility and mutual respect shown in the "Rumble in the Air Conditioned Auditorium" to our presidential debates. To be fair, it is easy to be frank and reasonable when there is nothing tangible at stake. Over the course of an hour and a half, moderator E.D. Hill guided the men through a variety of issues central to Americans today, from health care to foreign policy to the role of journalism in society. The most important question posed to the two men during the debate was one neither of them chose to answer verbally, "How is it that two personalities such as yourselves that are almost polar opposites politically show willingness to come together when Congress can't. What advice would you give Congress?" Stewart responded by sitting on O'Reilly's lap.
Journalism and Justice
Date: May 23, 2013
Show: The Daily Show
Most uncomfortable moment: "If you really cared about the Muslim community, you would bring in a Muslim host."
This marked one of the warmest exchanges between Stewart and O'Reilly. Though O'Reilly came on to promote his book, Keep it Pithy: Useful Observations in a Tough World, the timing proved interesting. This was right around the time that allegations surfaced that the IRS was targeting right wing organizations, and that the Department of Justice was looking at FOX News internal emails. On this occasion, Stewart and O'Reilly found natural common ground defending the media against government intervention. Early in the interview Stewart says, "It appears that the Department of Justice is really overreaching. Journalists. And that's troubling."
There are certainly few things that Stewart and O'Reilly can agree on, but journalistic independence from government intrusion is definitely one of them.
On Obamacare, Syria, and Leadership
Date: Sept. 20, 2013
Show: The Daily Show
Most uncomfortable moment: "I don't care if he put on a dress and lipstick and sashayed his pretty little ass around the White House and said, 'Look at me.'" (Stewart, on Obama and Syria)
Though O'Reilly technically made this appearance to promote his latest book, Killing Jesus (catchy title, no?), they spent the segment discussing Obama's leadership in terms of foreign and domestic policy. They started with a debate on Obamacare. The discussion quickly expands to how they feel laws should be passed and enforced. O'Reilly argued that the will of the people should be enforced, even if that means not enforcing a law that has been passed. Stewart countered, by pointing out that 90% of Americans are in favor of gun background checks. O'Reilly, surprisingly, agreed. He said, "If you have to register your car, you should have to register your bazooka."
Next, they discussed Syria. O'Reilly criticized Obama for backing down from his military "red line" there. Stewart responded with, "You said that you shouldn't take in to account any changing factors, and do what you said you were going to do." O'Reilly went on to argue that the image of the President matters, while Stewart insisted that all that matters is the result of the actions. To Stewart, it doesn't matter if Obama decides to "put on a dress," so long as the results work out.
This is by far one of the more wonkish exchanges between O'Reilly and Stewart. They seem more like professors than media personalities here, as they get into a serious debate about the role of the Executive.
The Battle Over White Privilege
Date: Oct. 15, 2014
Show: The Daily Show
Most uncomfortable moment: "They have to live there. Is that what you're telling me?" (O'Reilly, on low-income housing for African-Americans)
In the latest round of debate between Papa Bear and Stewart, we saw once again that these two men have become jovial, comfortable sparring buddies over the years. Even when they raised their voices at each other, there was a winking "there you go again" look in the eyes of the person being shouted down. The first minute or so played like a political odd couple bit, with Stewart referring to Bill as "William," and admitting that he didn't read the book O'Reilly had come there to discuss. For his part, O'Reilly quipped, "You're a director now. You have a vampire movie coming out."
Stewart quickly dispensed with the pleasantries (or lack thereof) about a minute and a half in and announced his goal for this round. Stewart said, "I want you to admit that there is such a thing a s white privilege." Predictably, O'Reilly trotted out his typical talking points, pointing out that Asian-Americans have a higher median income than whites and that both President Obama and Oprah are black.
Light-hearted, the two men exchanged their typical talking points. Though Stewart landed an early blow when he said, "There has a systemic ... systemitized subjugation of the black community. Would you not agree with that?" And O'Reilly responded, "Sure," they both got in the sound bites their respected bases would expect. The debate climaxed with shouted familiar O'Reilly-Stewart talking points.
O'Reilly said, "If you work hard, if you get educated, if you're an honest person, you can make it in America."
Stewart said, "If you live in a neighborhood where poverty is endemic, it's hard to work hard. It's hard to get an education."
O'Reilly retorted, "That was then. This is now."
And the most contentious friendship in cable news rolled on.