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Leonardo's grotesque figures have inspired numerous writings focusing on the artist's scientific approach to the study of nature and his notes discussing the painter's imagination. Most historians have either contextualized the drawings within the field of physiognomy, or have approached them from a psychoanalytical perspective. This paper instead focuses on the aged nature of Leonardo’s grotesque subjects whose withered and deformed physiognomies are often contrasted with the idealized profiles of youthful figures. While some of the grotesques are carefully worked drawings, others are schematic sketches that speak to Leonardo’s adaptation of suggestive lines and ambiguous forms. Several small-scale drawings in Windsor Castle, for example, explore extreme convex and concave features through a carefully controlled manipulation of the pen. This paper will place the grotesque figures within Leonardo’s practice of drawing and will argue that they can be interpreted as statements about the passage of time and destructive force of nature.