 Max PomerancJosh Waitzkin | Josh Waitzkin |
 Joe MantegnaFred Waitzkin | Fred Waitzkin |
 Joan AllenBonnie Waitzkin | Bonnie Waitzkin |
 Ben KingsleyBruce Pandolfini | Bruce Pandolfini |
 Laurence FishburneVinnie | Vinnie |
| MMichael NirenbergJonathan Poe | Jonathan Poe |
 Robert StephensPoe's Teacher | Poe's Teacher |
 David PaymerKalev | Kalev |
 Hal ScardinoMorgan | Morgan |
 William H. MacyTunafish Father | Tunafish Father |
 Vasek SimekRussian Park Player | Russian Park Player |
 Dan HedayaTournament Director | Tournament Director |
 Laura LinneySchool Teacher | School Teacher |
 Anthony HealdFighting Parent | Fighting Parent |
 Steven RandazzoMan of Many Signals | Man of Many Signals |
| CChelsea MooreKatya Waitzkin | Katya Waitzkin |
 Josh MostelChess Club Regular | Chess Club Regular |
 Josh KornbluthChess Club Regular | Chess Club Regular |
 Tony ShalhoubChess Club Member | Chess Club Member |
 Austin PendletonAsa Hoffman | Asa Hoffman |
 Tom McGowanReporter | Reporter |
| OOna FletcherReporter | Reporter |
| KKamran ShiraziSelf | Self |
| RRoman DzindzichashviliSelf | Self |
| JJerry Poe McClintonPark Player | Park Player |
| MMatt De MattNight Park Player | Night Park Player |
| VVincent SmithWashington Square Patzer | Washington Square Patzer |
| JJerry RakowWashington Square Patzer | Washington Square Patzer |
| WWilliam ColgateStatistician | Statistician |
| TTony De SantisJounalist | Jounalist |
