This paper examines the troubling relationship between the identity of the male artist and female sexuality during the rise of early modernism by comparing two literary works: Charles Baudelaire’s poetry collection Les Fleurs du mal and James Joyce’s novel A Portrait of the Artist as a Young Man. Portraying prominent female characters as a means to define the authors’ own modern aesthetics, both Baudelaire and Joyce perceive underlying tensions between biological reproduction and artistic creativity, prompting them to explore in detail the relationships between gender, sexuality, and the production of literature. For Baudelaire, the male poet as flaneur derives voyeuristic pleasure from his imaginary lesbian narratives, and his aesthetic awareness of the self that emerges is contrasted with the “sterile” nature of female homosexuality. Joyce’s Stephen Dedalus in Portrait, on the other hand, adopts a more ambivalent relationship towards women: like Baudelaire’s speaker, Stephen usurps the generativity of women by replacing meaningful relations with imaginary ones, subsequently deriving literary inspiration; at the same time, however, these attempts bespeak deeper anxieties towards his inability to attain artistic autonomy, ultimately reflecting increasing vulnerabilities in the modern male artist’s perceptions of self-contained subjectivity. Published half a century apart, these two works marked critical junctures in the emergence of modernism, and a comparative approach thus allows us to trace shifting ideologies of modern personhood and gendered identity.