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| Edward Norton | Monty Brogan |
| Philip Seymour Hoffman | Jacob Elinsky |
| Barry Pepper | Francis Xavier Slaughtery |
| Rosario Dawson | Naturelle Riviera |
| Anna Paquin | Mary D'Annuzio |
| Brian Cox | James Brogan |
| Tony Siragusa | Kostya Novotny |
| Levani | Uncle Nikolai |
| Misha Kuznetsov | Senka Valghobek |
| Isiah Whitlock Jr. | Agent Flood |
| Michael Genet | Agent Cunningham |
In New York City in the days following the September 11, 2001, terrorist attacks, Monty Brogan steels himself for a lengthy jail term. Brogan is a convicted drug dealer about to start a seven-year prison sentence, and his final hours of freedom are devoted to hanging out with his closest buddies and trying to prepare his girlfriend, Naturelle Riviera, for his extended absence.
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