In North Africa, from the eve of French colonial conquest to independence, we find transvestism—individuals cross-dressing as other races, other genders, other religions. That transvestic figures not only existed but were an important reality in colonial North Africa seems paradoxical, for French and British empires were predicated upon dividing colonizer from colonized. Yet from the eve of French conquest, we find Europeans dressed as native Arabs and Jews, Jews passed as Muslims, women created new personas as men. Transvestites blur boundaries between European and native, Jew and Arab, and challenging the boundary itself (Marjorie Garber). In the postcolonial era, drag seems to cut the other way; it is North Africans who play with multiple genders/languages/races. Two prominent French-Jewish-North African male comedians perform standup routines by dressing as women and code switching between French and Arabic. A contemporary Moroccan visual artist calls herself “Lalla Essaydi,” (“Madame-Sir”), and appropriates the historically male languages of European Orientalist painting and Moroccan Islamic textual calligraphy for a woman-centered photographic art. Somehow, transvestism allows one to speak in multiple voices, to speak a lived experience that is layered and fragmented, to say what cannot otherwise be said. Transvestism allows the speaker to be me and not-me. As Gad El Maleh says with the title of his drag standup, “L’Autre c’est moi, “The Other is Me.” The ubiquity of drag raises questions about what drag is, why it was, and what it means in the colonial context. Historical inquiry will show the times and situations in which identities ossify and drag becomes subversive. What is the boundary, how is it imagined, who polices it, when and why? How does drag differ from colonial hybridity, a goal of French colonial empire? The objective of this paper is to provide a historical framework for understanding drag and transvestism, from precolonial to postcolonial North Africa. This cultural history will draw upon literature, archives, ethnography, comedy, photography, and fine art.