This chapter traces the emergence of Joyce’s aesthetic from Stephen Hero to A Portrait of the Artist as a Young Man, analyzing the development of Stephen Dedalus as would-be artist in the context of Irish colonial experience. It pays particular attention to the influence of Oscar Wilde. Both Wilde’s Picture of Doran Gray and Joyce’s Portrait of the Artist belong to the Bildungsroman tradition, that is, to the novel of development, which their narratives challenge and transform by presenting the central character’s growth to maturity as deviating from cultural expectations rather than fulfilling them. Joyce’s narrative, however, points toward a new nation’s emergence.