“- Ellis Boyd 'Red' Redding: King me.
- Andy Dufresne: Chess. Now there's a game of kings.
- Ellis Boyd 'Red' Redding: What?
- Andy Dufresne: Civilized. Strategic...
- Ellis Boyd 'Red' Redding: ...and a total fuckin' mystery. I hate it.”

Morgan Freeman - Ellis Boyd 'Red' Redding
Tim Robbins - Andy Dufresne

“- Sgt. Deke Slater: I hate this stupid game.
- Que: That's only because you're so bad at it.”

Dylan Neal - Sgt. Deke Slater
Jennifer Tung - Que

“I don't know what's more pathetic - a man that plays chess with himself, or a man that doesn't see he's already lost.”

Willem Dafoe - General George Deckert

“- Stanley Motss: I bet you're great at chess.
- Conrad Brean: I would be if I could remember how all the pieces moved.”
Dustin Hoffman - Stanley Motss
Robert De Niro - Conrad Brean

“- Bart: Well, Jim, since you are my guest and I am your host, what's your pleasure? What do you like to do?
- Jim: Oh, I don't know. Play chess... screw...
- Bart: [quickly] Well, let's play chess.”
Cleavon Little - Bart
Gene Wilder - Jim