Rashi (Rabbi Solomon Yiṣhaki, 1040–1105) founds the school that stands as the basis for nearly all enduring religious and intellectual achievements to emerge from medieval Ashkenaz. Indeed, these achievements would live on in the way of life and mentality that informed Ashkenazic Jewry’s eastern Europe offshoots for centuries. Our course provides a panorama of Rashi’s and his students’ transformative contributions in such spheres as Talmud study and, especially, biblical interpretation. We explore how Rashi and his school related to such perennial topics as the election of Israel and exile and redemption while also opening a window on the world of medieval Ashkenaz in its larger challenging Christian milieu (for example, by tracing the rise and development of Ashkenazic anti-Christian polemical literature). Throughout, our study considers ways in which Rashi and his school forged an extraordinary fusion of tradition and conservatism on one hand and highly innovative creativity on the other.