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.