Let's point out the stupidly obvious: comedians are going to figure out how to make fun of Barack Obama. If I were a comedian, I'd do a bit about how everything with Obama is momentous. Show President Obama watching cartoons and then giving a speech to his kids on the possibility for eventual reconciliation between Tom and Jerry. Something about how the fundamental flaw in their thinking is not in coming up with ever more elaborate ways to physically assault each other, but in always resorting to war as a first resort. We should talk to our enemies.
In fact, you could play Obama's essential unfunniness, in ironic contrast to his appealing among young people, as a bit in itself. There's an irony about Obama that's completely untouched so far: that the young love him like they've loved no one since Kennedy, but Obama is the poster child for square grown-ups in everything but age. He takes everything so seriously. He seems like the only adult in Washington with his "no drama" mantra and disciplined campaign. He maintains a very traditional, even conservative family life. He has the perfect articulation of a Harvard man. He doesn't drink or womanize or even slouch. Even his "blow off steam" activity (basketball) is healthy! Hell, so far as I've seen, he's not even very good at telling a joke. Compared to both W. and Clinton, Barack Obama seems awfully proper and mature, even a bit stuffy. In fact, other than a dubious Jay-Z reference in one stump speech during the primary, there's little to indicate that Obama is "cool" in any traditional sense.