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This essay revisits Plato’s Philebus, his most advanced dialogue on the question of pleasure and the good life, in order to provide a philosophical clarification of Lacan’s concept of enjoyment (jouissance). Starting from Plato, I also propose a Hegelian-style account of the history of pleasure, culminating in Freud’s paradoxical notion of the “unfelt pleasure” of the neurotic symptom. The essay concludes with an examination of philosophy’s determination of philosophical pleasure as the best pleasure, looking at how the theory of pleasure ends up in the pleasure of theory. How does psychoanalysis both affirm and subvert this ancient ideal of intellectual pleasure, the “theory drive”?