The following article has emerged from an experimental, interdisciplinary course, co-taught by the authors in the fall of 1996, entitled “Exile: Jews, Literature, and History.” From the dozens of primary texts used in the course, we have selected six to illustrate the literary-conceptual analysis employed. Beyond the intrinsic aesthetic appeal of the passages, they have been chosen to exemplify the diversity of relevant material: in genre (poetry, disputational and homiletical literature, drama, fiction, memoir), cultural-historical context over the past millenium (Muslim and Christian Spain, eastern Europe, twentieth-century Egypt and Israel), community (Sephardic, Ashkenazic, and Middle Eastern Jews) and language of authorship (Hebrew, Arabic, and English). Starting with one of the most familiar texts of post-biblical Jewish literature, we move in the modern period to decidedly less-known works, challenging simplistic assumptions about “canon” in research about the Jewish past. The juxtaposition of pre-modern and modern texts is intended to highlight both the continuities and the ruptures brought by the twentieth century.The authors would like to express their gratitude to the William T. Kemper Foundation for sponsoring the Faculty Award program at Washington University in St. Louis that supported the development of this course.