just trying to see if jack even can come up with a good explanation of his own jokes.
For instance:
Since Obama and Hillary are in direct competition with each other for the democratic nomination, the idea of them being in the same car, going the same direction is misrepresentative. While he may be "driving her to run" as jack suggested, that would be more easily conveyed by some sort of "goading" imagery to indicate the competetive nature of their relationship.
So, why this picture then? The only reason why this picture was suggested is because he's black and she's a white female. It has (at best) a marginally thin reference to their political relationship. You may as well have colin powell driving laura bush in a car and giggle at that.
This is why the joke is no more than a bunch of guys laughing, saying to themselves "heh heh, she's a woman. heh heh he's black. That's funny"