This dissertation adopts a postmodernist approach to explore the different types of transgression-the violating, breaking, surpassing, or criticizing of the dominant culture-in six representative Spanish novels and films produced at the end of the twentieth-century in Spain: Una mala noche la tiene cualquiera, by Eduardo Mendicutti; Las edades de Lulú, by Almudena Grandes; Historias del Kronen, by José Angel Mañas; Amor, curiosidad, prozac y dudas, by Lucía Etxebarría; Todo sobre mi madre, by Pedro Almodóvar; and Solas, by Benito Zambrano. The project concentrates on four ways in which the cultural and hegemonic values and traditions of Post-Franco Spanish society undergo narrativized disruption: transgressions against the older generations, against the traditional nuclear family, against conventional forms of sexuality, and against the body of the past. In this study I show not only how these transgressive discourses work to destabilize oppressive critical, political, social, and gender categories within mainstream Spanish society but also how certain contradictions, ambiguities, and paradoxes inhere in these transgressive attempts. In this sense, the main objective of this study is to problematize the concept of transgression in contemporary Spanish culture and society, questioning the binary dichotomy between order and transgression, and emphasizing the dynamism and interaction between both terms. The dissertation considers the difficulty if not impossibility of radical subversion in the Spanish postmodern context and attempts to clarify the ambiguity and paradox that characterize the multiple transgressions found in these texts. This study problematizes the reading of texts that in a sense rebel against the entrenched normative legacy of the Spanish dictatorship at the end of the Millenium, destabilizing some of the 'normative' values of society, and tries to make more evident the great potential of the transgressive discourses found in these narrative and cinematic productions. In their paradoxical formulations, they celebrate difference itself and speak the voices traditionally silenced.