This study explores the topsy-turvy art of Hans Baldung Grien (1484/5–1545), where virgins are seductive, witches are beautiful, and both are dangerous yet enticing. Baldung’s pictures responded to and perpetuated anxieties and doubts about perception that permeated the culture of Reformation Germany. Such anxieties transformed virgins into vixens and produced the stereotype of the witch. Baldung’s pictures anticipated anxious viewers who understood erudite, inside jokes and were inclined to doubt what their eyes seemed to perceive. Understanding the role of doubt helps explain the power of Baldung’s Reformation period pictures, such as the painting Madonna with Parrots, 1533, and the print Witches Sabbath of 1510. These images engender a kind of doubt about accurate perception that preoccupied artists and theologians, and presumably viewers, during the Reformation.