A reader writes:
"He knew that what Washington pundits really craved was not the truth, but a sense of their own importance. So he let them throw him a dinner party."
But you are clearly on to something. I remember with Bill Clinton, he had way of making people feel they were "the only person in the room:" and that they "mattered to him" as many articles during his tenure claimed. But what Obama seems to have is the ability not to appear as if he is acting, faking it. That is why comedians were able to mock Clinton's lower lip biting and other such gestures meant to show how much he cared. Why do comedians have such a hard time mocking Obama? Some say it is because he is black, and they don't want to be seen as racist; no, that's not it. They mock Jesse Jackson and Al Sharpton all the time.
They can't mock Obama because he is not a faker, not a schmoozer, not a dolt, not a skirt-chaser, not a charlatan, etc. etc. Obama has the realness that comes from the hard psychological work that it takes to really get to know yourself and come out on the other side unafraid of whatever might come your way. That is decidedly not funny.