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| Ebon Moss-Bachrach | David |
| Devon Aoki | Picasso |
| Capone | Damon |
| Robert Stapleton | Jay-Z |
| Rashida Jones | Layna |
| Kevin Hart | P-Diddy / Cop 1 / Dance Coach / Hyper Rapper / H. Lector |
| Gerald Kelly | Funkmaster Flex / Biggs / Angry Blackman |
| Damon Dash | Fresh to Def |
| Chloƫ Sevigny | Sexy Woman No. 1 |
| Kari Wuhrer | Sexy Woman No. 2 |
| Jamie-Lynn DiScala | Sexy Woman No. 3 |
| Mr. Blue | A&R Guy / Hipster / Lew Chaplin |
| Sale Johnson | Enchante R&B Singer No. 1 |
| Lorraine Bracco | Enchante R&B Singer No. 2 |
| Duncan Sheik | Well-Dressed Man |
| James Toback | Lyor Cohen |
| Michael Musto | Himself |
| Mark Ronson | Engineer |
| Flavor Flav | Reporter No. 1 |
| Philip Bloch | Slick Man |
An ambitious white reporter, David Katz, gets an assignment covering rappers Damon Dash and Jay-Z, during which he tries to insinuate himself into the hip-hop world. When he overhears an executive telling Damon that his career at record label Roc-A-Fella is done, David is the first to report it, which gains him notoriety and his own column at a leading hip-hop magazine. Unfortunately, he also ignites a bitter feud between Damon and Jay-Z.
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