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W. E. B. Du Bois’s Dark Princess (1928) pointedly uses Spirituals and dandyism to interrogate cultural hierarchies. This essay highlights the shared genealogy between early twentieth-century African American writing and two bifurcating branches of nineteenth-century dandyism: the European tradition of Baudelaire and Wilde and the blackface tradition of the minstrel show. Tracing these lines of transmission reveals an unexamined embranchment of literary modernity’s family tree and demonstrates how Du Bois’s novel repurposes this legacy for the twentieth century.