Gargoyles and grotesques occupy one of the most unsettling positions in the history of art and architecture. Emerging in the Gothic cathedrals of medieval Europe, these distorted and often monstrous figures were not merely decorative. True gargoyles served a functional purpose, channeling rainwater away from stone walls, while their purely sculptural relatives—the grotesques—were designed to confront viewers with fear, excess, and bodily instability. This talk will trace the afterlives of the gargoyle and grotesque in modern architecture, including their revival in nineteenth-century restorations and their surprising persistence in twentieth-century skyscrapers such as New York’s Chrysler Building.