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

New York gangster Ben 'Bugsy' Siegel takes a brief business trip to Los Angeles. A sharp-dressing womanizer with a foul temper, Siegel doesn't hesitate to kill or maim anyone crossing him. In L.A. the life, the movies, and most of all strong-willed Virginia Hill detain him while his family wait back home. Then a trip to a run-down gambling joint at a spot in the desert known as Las Vegas gives him his big idea.