The Challenge to Theory in Arabic in the 21st Century Although Arabic literature has not been consistently involved in 'theory' as understood and disseminated in the academia in the West, there are nevertheless a number of Arab intellectuals' positions that engage with this issue since the reliance on ' the enlightenment ' discourse in nahda and post-nahda writings and theorizations. In self narratives and a number of treatises, counter narratives, metafiction, and poetic pieces this engagement with the enlightenment discourse sets the cultural and even political scene for achievements and setbacks that require further investigation. But this engagement falls historically between 2 prominent cultural blocks: one relates historically to cultural heritage and specifically literary and philological theory, and another moves headlong into the offers of the cyberspace and its post modernity transactions. The first portion of this paper interrogates the limits and prospects of classical and postclassical theories in relation to poststructuralist, postcolonial, and postmodernist approaches, like Todorov's updated perspective of the fantastic in relation to al-Qazwini's specific explication of this matter for example. The second part explores the impact of the encroaching media and communication on narrative and poetic products. It is my purpose to assess this thorny entanglement through a number of cultural examples and theoretical explications in order to map out probable tracks in theory and cultural products. Both parts intertwine in genealogies of similitude, resemblance, rational reasoning, and technologies of power that make up an enormous cultural production worthy of interrogation and mapping.