When: Februray 2010 
Where: The O'Reilly Factor  

There have been several bouts between Stewart and O'Reilly over the years, and they are always a pleasure to watch. In their 2010 match, they kept it relatively civil for the first few minutes, debating President Obama's progress to date. Then the gloves came off.

Stewart started with, "You've taken a cyclonic...political wing and you've cut it a little bit." He mocked Fox and Friends, saying "I googled 'Czar,' did you know that's a Russian word?"

Though O'Reilly managed to restrain himself far more than usual, he referred to Jon Stewart's writers as "pin heads" and accused him of being dishonest in his news coverage. We have to give O'Reilly credit where credit's due though, he got through the whole thing without yelling.