There's a great interview that the podcast Irreligiosophy did of Silverman, which is where I first heard of him. He explained that backstage, Bill O'Reilly isn't a gaping idiot. He's a bright, erudite man. So when he really had to confront him on Fox - the "tide goes in, tide goes out" conversation that produced the famous meme face - he realized during the moment that he made that face that O'Reilly was playing a character, and you can't win an argument against a character. His goal during those TV spots is to get out on that particular news channel what he hopes and wants to say, in the confines of what the "characters" Fox News has up there build around him.
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