Thomas Mann’s literary obsession with Nietzsche’ philosophy was lifelong, continuously evolving, and constantly subversive. His early short stories were preoccupied with Nietzsche’s Wagner reception and cultural critique of decadence; the middle-period novella, “Death in Venice” engaged with the mythical pair of the Dionysian and Apollonian; the novel Doktor Faustus, his self-proclaimed “Nietzsche book,” combined Nietzsche’s biography, aesthetics, and “the problem of the German.” In each phase, Mann’s reception was never simply dutiful, but rather mischievously pitted one Nietzschean position against another, deriving dramatic force from the often contradictory capaciousness of his thought. This chapter focuses on a work not always considered as part of Mann’s Nietzsche reception: Confessions of Felix Krull, Confidence Man, an early short story later expanded to become Mann’s last novel. The text playfully juxtaposes Nietzsche’s “problem of the actor” and his ideal of self-fashioning, what Alexander Nehamas describes as Nietzsche’s “life as literature.” It explores issues of style, taste, parody, “gay science,” and the concerns attendant upon the translation of Nietzsche’s literary philosophy back into literature proper. It shows how the parody and mockery of Nietzschean ideals cannot help but fall in with the models they turn on, and the implications for our understanding of Nietzsche’s own writing.