The pleasure and the pain of the listener are intensely negotiated in the Odyssey, until reconciled in the figure of Odysseus. For a modern reader such issues bring up an instrumental concept discussed by Edward Bullough in the early twentieth century, that of psychical distance. This chapter suggests that contrary to current assumptions, in the Odyssey aesthetic pleasure is steadily sought out in spite of a listener’s lack of psychical distance. Two further points are emphasized. First is the importance of underexamined aspects of Plato’s Philebus for understanding mixed pleasure as an aesthetic type of pleasure. Further comparisons between Platonic and Homeric approaches to a listener’s weeping illuminate the subtleties of the latter. Second are Kant’s sparse and insufficient references to weeping as a mode of response. A modern reader of the Odyssey might trace in Odysseus’s aesthetic response a judgment of taste, despite Kant’s own exclusion of this type of judgment from the realm of emotion.
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