In recent decades, there has been renewed interest in the fifteenth-century philosopher and theologian Nicholas of Cusa, especially as a figure offering insights into the genealogical development, the possibilities, and the challenges of modernity—topics expounded in the twentieth century by Martin Heidegger, the great diagnostician of the modern technological condition. While Heidegger’s philosophical indebtedness to mystical Christian traditions has been well-established by recent scholarship, there has yet to be a major study connecting Nicholas of Cusa and Heidegger, who in many ways bookend the modern epoch. In filling that lacuna, this dissertation draws out the shared thematic concerns of these two prolific thinkers and critically reappraises the thought of Cusanus and Heidegger on three central themes: the singularity of the human individual, the fundamental sociality of the human, and the bounds and possibilities of human creativity. My comparative analysis demonstrates that Cusanus at the origins of modernity and Heidegger at the end of modernity offer two different but complementary ways to understand the uniqueness of each human individual, whose singularity is threatened by the leveling forces operative in industrialized late-capitalism and in certain mechanized forms of production. The dissertation further argues that Cusanus’s communal practice of mystical contemplation, which attempts through discourse to reconcile uniqueness with communal commensurability, parallels the question in Heidegger’s thought about how individual authenticity can be experienced, enacted, and publicly communicated. Finally, the dissertation argues that Cusanus’s and Heidegger’s accounts of creativity suggest potential antidotes to the excesses of automatization and the aesthetic deterioration associated with the modern technological condition. Both Cusanus and Heidegger propose ways to read works of art as the kinds of poetic making that can institute and sustain a community, while opening the way to new forms of thinking and of inhabiting the world