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.
Robert Downey Jr.
as Terry Donager
Scott Caan
as Scotty
Stacy Edwards
as Sheila King
Allan Houston
as Dean Carter
Gaby Hoffmann
as Raven
Jared Leto
as Casey
Claudia Schiffer
as Greta
Brooke Shields
as Sam Donager
Joe Pantoliano
as Bill King
Kidada Jones
as Jesse
Marla Maples
as Muffy
Bijou Phillips
as Charlie
