Best of Enemies: Jon Stewart's 10 Favorite 'Daily Show' Targets

From Fox News to Arby's, the folks commonly caught in the comedian's crosshairs

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Bill O'Reilly

What angered Stewart most about host of The O'Reilly Factor wasn't the man's politics — it's that he believed in his heart that the political blowhard was smarter than the moronic Fox News talking points he uttered. The two men's interactions on The Daily Show played out like emotional interventions: Stewart implored his frequent guest to stop dumbing down his beliefs for ratings; O'Reilly countered by playfully needling Stewart and his fellow liberal "pinheads." For all their bitter political differences, the duo always had easy rapport and an understanding that they were both playing parts in a silly act of theater — which is what made their double act so consistently watchable.You'd always know Jon was getting to Bill when Papa Bear would spit out a grumpy "Stewart!" in his responses.

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