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.