​Date: Sept. 17, 2004
Show: The O'Reilly Factor
Most uncomfortable moment: "You asked me why I'm such a bad person. Is that serious question?" —​O'Reilly, referencing his Daily Show appearance

Just a few years after O'Reilly stopped by the The Daily Show to discuss his approach to political journalism, Stewart stopped by The O'Reilly Factor to explain how he isn't a political journalist. "We're not competitors in terms of content. You're a news show and we are a comedy show." he said. Stewart has fallen back on this refrain a number of times over the years, and to O'Reilly's credit, Bill tries to hold Jon's fee to the fire. "What do you want the audience to get out of your discussion with Kerry? Yucks or anything else?" he asked Stewart. While many conservative pundits were, and still are, quick to accept Stewart's self-proclaimed position of court jesterO'Reilly saw early on that Stewart was at the helm of something far more than important than just a comedy show.