In the final book of Plato’s Republic, Socrates bans the poets from his ideal city. According to Socrates, the poets bring about corruption and decadence: instead of pursuing and producing the truth, poets reproduce falsehoods – “images” as opposed to “the originals.” Only the philosophers, Socrates says, oversee the truth. However, Arthur Schopenhauer, the self-proclaimed inheritor of Platonic philosophy, seems to flip this idea on its head. Poets do manufacture images, but these images, Schopenhauer claims, are knowledge par excellence. In this paper, I explore Schopenhauer’s contribution to the “ancient quarrel between philosophy and poetry” and argue that, for him, poetry is not only a truth-tracking endeavor, but is invaluable to the practice of philosophy itself. I, then, turn to Schopenhauer’s “son,” “pupil,” and “born psychologist,” Friedrich Nietzsche, to examine the relationship between poetry and health. I conclude by suggesting some implications that Schopenhauer’s aesthetic theory might have for contemporary philosophers.