From Gawker's "Guide to Barack Obama’s Coolness for Politicians and Journalists":

Barack Obama is not cool, and it is journalistic malpractice to describe him as such. (Mobute has done a good job of explaining how, in many situations, when people call Obama "cool" they really just mean "black." I am here talking about actual coolness.) I do not go to cool people and ask them to poorly explain the minutiae of American elections; and I do not go to political journalists and ask them how to wear sunglasses and where to buy drugs. Political journalists are deeply uncool people, and not in the way where they're, like, so uncool that they're actually cool. They are constitutively uncool. They are not to be trusted on matters of coolness.