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.