This essay explores the aesthetic and theoretical implications of canonical urban writing in French literature from roughly 1830 to 1930. Beginning with Balzac and the popular works of his time such as the tableau, I trace the rise of the flâneur as the quintessential embodiment of new modes of reading and writing the city. I then turn to Baudelaire’s poetry and aesthetic theory, which reveals the conception of the city as materials awaiting metamorphosis through symbolism and allegory. In the fiction of Zola, I analyze the eponymous grand magasin of Au Bonheur des Dames as a paradigmatic site of phantasmagoria that produces the counter-force of the conte within Zola’s realist representation. I then read two essential Surrealist novels as reflective of these issues of representation that continued to vex the twentieth century. The Surrealist appropriation of flânerie, their preoccupation with chance and with le merveilleux, their insistence upon the visual and its power of enchantment—these concerns ground them firmly within the French literary tradition at the same time as they seek to break with it. In these works, are utopian spaces realized, or do such efforts end in disenchantment? does the flâneur reach new heights in literature or simply reenact ad infinitum Icarus’s ill-fated flight? With such questions in mind, I explore the ambivalence that prevailed in the urban literary aesthetics of nineteenth-century writers, and which continued well into the twentieth century through the works of the Surrealists and the criticism of Walter Benjamin.