Rich Bower (Power) is an up-and-coming star in the hip-hop world. Everyone wants to be around him, including Raven (Gaby Hoffman) and her fellow upper-class white high school friends. The growing appeal of black culture among white teens fascinates documentary filmmaker Sam Donager (Brooke Shields), who sets out to chronicle it with her husband, Terry (Robert Downey Jr.). But before Bower was a rapper, he was a gangster, and his criminal past comes back to haunt him and all those around him.