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- CJ Adams as Timothy Green
- Jennifer Garner as Cindy Green
- Joel Edgerton as James Green
- Dianne Wiest as Ms. Crudstaff
- Odeya Rush as Joni Jerome
- Rosemarie DeWitt as Brenda Best
- Ron Livingston as Franklin Crudstaff
- David Morse as James "Big Jim" Green Sr.
- Common as Coach Cal
- Shohreh Aghdashloo as Evette Onat
- M. Emmet Walsh as Uncle Bub
- Lois Smith as Aunt Mel
- Lin-Manuel Miranda as Reggie
- James Rebhorn as Joseph Crudstaff
- Michael Arden as Doug Wert
- Rhoda Griffis as Dr. Lesley Hunt