Following up my observations on Obama as the cool candidate, another way of looking at it -- indeed, probably the correct way of looking at it -- is in terms of Garance Franke-Ruta's old observation (that I can't find on Google for some reason) that Hillary Clinton is the middlebrow candidate in the race. That, more than cool/uncool, captures the Wire versus Ugly Betty dynamic.
And it's also, of course, Clinton's big advantage. TV critics like The Wire but Ugly Betty has a much bigger audience. At the end of the day, how many people know who will.i.am is?
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