No discussion of literature and poetry in connection with the problem of authenticity can fail to evoke their epochal shadow of suspicion of the notoriously non-authentic. This goes back to Plato’s Republic where questions regarding the inauthenticity of the mimetic arts result in a decisive verdict against poetry, which would consequently be banned from the state. What unfolds in Plato’s Republic could be called the first debate in Western philosophy on the question of authenticity. In its dialogizing we can already observe the formal, rhetorical and typological structures of argumentation that have defined the discourse on authenticity with regard to literature ever since. By systematizing Plato’s arguments into a “Configuration of the Authentic vs. Inauthentic” (‘gradualism’ / ‘distance vs. proximity’ / ‘fleeting vs. lasting’ / ‘being vs. seeming’ / ‘truth vs. untruth’ / ‘derived vs. original’ / ‘emphatic rhetoric of pathos’) the paper explores the interconnectivity of Joyce’s “Epiphanies” (1898/1904) and Hofmannsthal’s “Chandos Experience” (1902) as witnesses to the quest for literary authenticity at the turn of the 20th century.