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- Reece Thompson as Hal Hefner
- Anna Kendrick as Ginny Ryerson
- Nicholas D'Agosto as Ben Wekselbaum
- Vincent Piazza as Earl Hefner
- Aaron Yoo as Heston
- Josh Kay as Lewis Garrles
- Denis O'Hare as Doyle Hefner
- Maury Ginsberg as Mr. Lewinsky
- Jonah Hill as The Junior Philosopher
- Dan Cashman as The Narrator