The connection between Brer Rabbit and the story of the Jewish community after 70 CE is that both are recorded in literatures of exile. As a result, they share a significant quality—the double voice—deployed as one of many literary strategies for survival under oppression. Using passages from Brer Rabbit and Lamentations Rabba, this article focuses on riddles and trickster tales because they present an especially striking witness of the double voice as expounded within African-American literary theory. These genres appear in the folklore of most cultures, but their encoding enables a unique inversion of cultural meaning for subaltern and dispersed peoples, which gives the tales remarkable power to fashion and sustain identities, and to articulate the complexity of their experience. They absorb the imagery and language of the dominant culture, yet re-signify their meaning in the process of assimilation. Both elements of this voice—the adoption and the inversion—are essential representations of the authors or redactors. Separated by time, space, language, culture, and context, the tales of Brer Rabbit and the Palestinian rabbinic midrash speak to each other through this strategic polyphony.