This article examines Nietzsche’s engagement with romanticism. It contrasts his early romantic period, and the influence of Goethe, Hölderlin, and Richard Wagner, with his later attempts to “cure himself” of all romanticism. It considers the extent to which Nietzsche shared Goethe’s famous equation of the classical with health and the romantic with sickness—which Nietzsche most often calls decadence. It argues that there are deep programmatic and even textual affinities between Nietzsche’s Zarathustra and Hölderlin’s Hyperion. It was fundamentally through his engagement with Wagner that Nietzsche first came to realize that romanticism actually embodied a life-denying repudiation of this world rather than a genuine path to cultural renewal.