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| Billy Bob Thornton | Mr. Woodcock |
| Seann William Scott | John Farley |
| Susan Sarandon | Beverly Farley |
| Amy Poehler | Maggie Hoffman |
| Ethan Suplee | Needleman |
| Josh Shada | Schwartz |
| Emily Wagner | Principal |
| Jacob Davich | Nederman's Brother |
| Melissa Sagemiller | Tracy |
| Stephen Monroe Taylor | Oates |
John Farley, a self-help author, returns to his hometown and makes a shocking discovery: His mother is about to marry his former gym teacher, a man who made John's life a living hell during his high-school years. John sets out to prevent history from repeating itself by stopping his mother's marriage to his nemesis.
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