Hagiographical and literary depictions of "holy folly" describe the phenomenon in various ways but emphasize the adoption of shocking and unconventional behavior in order to deflect public admiration that would be spiritually harmful to its practitioners. Yet paradoxically, once holy folly becomes a recognized strategy, it raises the same problems it is meant to avoid. Taking the paradoxical character of holiness as a starting point, this essay examines representations of the holy folly tradition in Russian literature, including the work of Dostoevsky, Mikhail Bulgakov, and Eugene Vodolazkin.