This chapter sets out to take a close look at the figure of the artist in the novels of Joyce and Rushdie. That none of their writings are sans such a figure is surely significant. What is of particular interest to me here is the crucial importance of the city in the formulation and development of their artistic credos and personae. An analysis of the engagement between the artist and the city can uncover some of the aporias of seizing upon the city as artistic material and prise open questions of representation, representability and individual subject-positions. The modalities, aspirations and limitations of these self-conscious engagements with the city can reveal as much about the artist in question as about the city that her/his art is inseparable from. In fact, I propose that the differences between early twentieth-century Dublin and late twentieth-century Bombay can be much more sharply crystallized by means of such an analysis. Further, I shall be using this discussion to deepen our understanding of the artistic enterprises of the two other artists my book is concerned with, Joyce and Rushdie.