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.