Whiteboys 1999

Danny Hoch is the irrepressible Flip, the hip hop poet of his own white boy crew. The son of a working class Iowa family, Flip just wants "to keep it real." In his mind, that means moving into the Chicago ghetto to live and write million-dollar rap hits like his heroes. He might look white, but he figures the color of his skin is just an error. Frustrated by the limits of his conventional white upbringing, Flip stands outside the standard high school cliques. Flip and his friends, Trevor (Mark Webber), James (Dash Mihok) and college-bound girlfriend Sara (Piper Perabo), drink forty ouncers, smoke Philly blunts, cruise around in James' truck and aspire to be gangsta rappers. Then they meet Khalid (Eugene Byrd), an upper class black kid recently transplanted from Chicago. When Flip gets him out of a run-in with the law, Khalid owes him. He agrees to take Flip and the gang to Chicago where Flip's fantasy gangsta world meets reality in a way he never imagined.