Part of me feels bad for liking this clip of President Obama talking NBA with Bill Simmons, like I’m buying into all the dumb “Who would you rather have a beer with?” stuff from the Bush elections, like I’m failing to acknowledge my own biases.
But on the other hand, just watch it, and keep Mitt Romney in mind as you do:

Sure, Obama doesn’t quite come across as Just Some Guy, but have you ever seen Romney look anywhere close to this natural? Does he ever come across as someone who is simply shooting the breeze about a subject he enjoys?
No, and it matters in an election, because of course there’s something to all the old dumb Bush cowboy stuff, in the sense that voters need to feel a sense of connection to a candidate. Beyond the perception that Romney is a flip-flopper and/or lacks orthodox conservative bona fides, his startling inability to elicit this sense in the average viewer or voter is why he is such a hamstrung candidate.