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| Danny Hoch | Flip |
| Dash Mihok | James |
| Mark Webber | Trevor |
| Piper Perabo | Sara |
| Eugene Byrd | Khalid |
| Bonz Malone | Darius |
| Dr. Dre | Don Flip Crew #1 |
| Rich Komenich | Flip's Dad |
| Annabel Armour | Flip's Mom |
| Lisa Jane Todd | Trevor's Mom |
| Jacqueline Willams | Khalid's Mom |
| Reno Wilson | Mace |
| Fat Joe | Don Flip Crew #2 |
| Dead Prez | Cornfield Rappers |
| Mic Geronimo | Friend of Mace |
| Doug E. Fresh | Parking Lot Rapper #1 |
| Slick Rick | Parking Lot Rapper #2 |
| Snoop ``Doggy'' Dogg | Himself |
Flip, James and Trevor are passionate hip-hop fans who yearn to become rappers during the ''gangsta'' era of the late 1990s. However, as white kids from comfortable suburban Iowa, they find that dream impossibly distant until Flip befriends Khalid, an African-American transfer student. When Flip and his friends press Khalid to take them to Chicago's notorious inner-city projects, they see the truth behind their secondhand thug-life fantasies.
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