Paul Auster's City of Glass and Orhan Pamuk's The Black Book both generated critical reception from deconstructive and poststructuralist angles. In this article, by pursing a historical materialist analysis, I explore how these postmodern city novels of the 1980s, which emerge from drastically different geographic, political, and cultural circumstances, respond to the impositions of global economic dynamics. In this context, I argue that the conflict between the apparent freedoms of globalization and the increasing entrapment of the postmodern subject constitutes the main dilemma of postmodern aesthetics. Auster's City of Glass and Pamuk's The Black Book register this postmodern dilemma in their respective forms through recourse to the metaphor of the "city as illegible text" and to the broken signifying systems of postmodern allegory. Focusing on these two literary techniques, I examine their differential appropriations in the core and the periphery of the world literary system in order to gauge how the experience of urban modernity-as shaped by particular cultural, social, and economic developments-contributes in turn to the shaping of literary form.