Despite what you think about Obama, he and his family aren't viewed as Uncle Toms not because their hip or cool, or modern. Its because he expanded his career by beating the streets of Chicago especially in some of the most violent, depressed, crime ridden areas of the city and tried to improve peoples living situations. He isn't even from Chicago but he wanted to make a different And for the most part, he wasn't making much money doing it either. People respect that more, then someone who mingles with the 1% and says crazy shit about his own people. Shit even some people are starting to look at Jay-Z as a Modern Uncle Tom, someone who has forgotten where they have come from, throws his closest people under the bus that helped his fame, and talks down to poor blacks.