Black and White (2000)

When high school hipster Charlie and her friends start hanging out with Harlem's aspiring rap artist Rich Bower and his group, the American Cream Team, each faction starts to ponder the other's true motivation. Fascinated by this collision of cultures, documentary filmmaker (and former rich girl herself) Sam Donager attempts to capture the phenomenon on camera with the help of her gay husband Terry. Meanwhile, NYPD detective Mark Clear wants revenge on his heartless ex-girlfriend Greta, who dumped him for Dean, a black star basketball player and a friend of Rich Bower. Before long, everyone wants something from someone else. As the chain of casual acquaintance comes full circle, worlds collide -- black and white, wealthy and wanting, uptown and downtown, innocent and malevolent until it becomes clear that nobody is really who he or she seems to be.