This article discusses Michelangelo's drawings for Vittoria Colonna in relation to poetry and prose by Michelangelo, Colonna, and their circle. It focuses on the intersection between debates about Church reform and the polemic about disegno (drawing or design) and colore (color or finish). Vittoria Colonna used the distinction between disegno and colore repeatedly in her spiritual poetry. In these and other writings, reform-minded thinkers did not offer consistent aesthetic and theological positions, but rather consciously articulated contradictions. Likewise, Michelangelo's drawings for Vittoria Colonna display a strategy of deliberate paradox, in that they are highly colored black-and-white drawings of a tearless tearfulness and a bloodless bloodiness.