Modern Arabic drama has been constructed in orientalist scholarship as an “importation from the West”; an instrumental appendix of modernity to substantiate the European primary institution of cultural and theatrical production. However, emerging critical studies have drawn attention to repressed evidence of authentic aesthetic strategies specific to Arab dramatic traditions and forms. The work of playwrights like Tayeb Saddiki in Morocco, Abdelkader Alloula in Algeria and Sa’dallah Wannus in Syria demonstrate a political anxiety to recast an original literary modus operandi. Tayeb Saddiki (1938-2016), trained in the French theatrical tradition, and a disciple of Molière, was particularly experimental in revalidating the artistic value of such dramatic classical techniques as halqa genre (open-air circle performance), classical maqamat (assembly) and l’bsat (social satire). In this paper, I examine Tayeb Saddiki’s distinct contribution in refashioning a postcolonial self-reflexive, syncretic, and open-ended Arab theatre that dismantles binary opposition between “modern” and “indigenous” dramatic traditions, and most significantly that rehabilitates the double bind of dramatic performance. Saddiki’s hybridized theatre is not only to entertain but also to create a space for the thinkable/ unthinkable. With thirty-two plays in Arabic and French, and the direction of more than eighty performances in the Arab world, Tayeb Saddiki’s impact remains his ability to transpose not only innovative dramatic devices, but also an inter-textuality and inter-performativity that promote an inter-play of reasons. From one of his first plays recasting a 16th century poet, Diwan Sidi Abder-rahman Al-Majdub (1966), to Maqamat Badia Ezzamane El-Hamadani (1971), all the way to his most engaging dramatic reinvention of the 10th century philosopher, Abu Hayyan Al-Tawhidi (2004), Tayeb Saddiki fuses new dramatic technique with trans-historical philosophical ideas. Ultimately, my argument shows how Saddiki has reconceived an Arab theatre that theorizes the idea of radical difference as a modernizing mode for a trans-national site of textual and theatrical practice.