Among the innumerable interesting things about Obama's candidacy is the lie that it puts to some of the most tired myths about black/white relations in America.
In particular, the myth that the historical marginalization of blacks has given them particular insight into the dominant (i.e., white) culture. This may have had some truth when black women frequently worked as "domestics" for upper-crusty whites and had to look the other way at the wife's pill-popping and junior's porn collection, but no more.
Obama has spent much of his adult life establishing his black bona fides in the armpit of South Side radicalism, but he's successful as a candidate because he was raised by and around whites and has developed a very keen instinct for Stuff White People Like. Your typical inner city ward heeler, however, has no idea. With the atomization of popular culture, poor, inner city blacks are probably more insulated today from nonblack culture than they ever have been in history.
For example, interviews with inner city American blacks now frequently need to be subtitled on TV - unthinkable 20 years ago, unless it was someone born in the 1800s and had lived his whole life on the Delta (white speech, as far as I can tell, hasn't changed much - so I don't think that's it).
I always figured the first black Presidential nominee would be a Republican or quite conservative Democrat, probably from a military background, or perhaps a sports background (or both, e.g., former Naval officer and basketball hall of famer David Robinson). I assume Colin Powell could have won the GOP nomination fairly handily in 1996 as a war-winning general, if only he'd wanted it.
In contrast, white Democrats haven't seemed to like black candidates much. They've looked down upon non-racialist pragmatic black politicians like former LA mayor Tom Bradley as Uncle Toms, yet also looked down upon racialist politicians popular with blacks like Rev. Jesse and Rev. Al as buffoons. So, Obama is the unexpected answer to their fantasies. A black candidate who has worked hard to establish a career for himself as a South Side racialist, but who is really a lit fic novel reading white man in a semi-black skin.