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.