Challenge him to a game of chess and purposefully misquote Shakespeare to the point that it drives him to suicide.
"What light through yonder window breaks? It is the east, and Juliet is the west."
"To be, or not to be—that is the answer."
"Is this a dagger which I see before you, The handle toward your hand? Come, let me clutch thee: I have thee not, and yet I see thee still not dead."