Female villains, both fictional and real, are subject to unconscious gender bias when part of their iniquity involves the disruption of male authority. Disney’s most popular animated villain, Maleficent, from Sleeping Beauty (1959) and Elizabeth Holmes of the now-disgraced blood testing startup, Theranos, reveled in their power, deviating from idealized feminine propriety. An analysis of scenes featuring Maleficent, the “mistress of all evil”, and coverage of Elizabeth Holmes, once the first self-made female billionaire, illustrate how powerful women with hubris are censured beyond their misdeeds. Elizabeth Holmes’ adoption of a deep voice and other masculine characteristics parallels Maleficent’s demeanor and appearance that signal female usurpation of traditional male power. Both antagonists also engage in finger pricking that penetrates the skin and draws blood, acts associated with symbolic male potency. The purported ability to bewitch, in conjunction with the adoption of patterns associated with male dominance, suggest that Maleficent and Elizabeth Holmes wield power over men and wield the power of men. Discomfort with the way in which magical powers were allegedly employed by these women echo historical fears of witches accused of appropriating male power. Furthermore, powerful women who encroach on male authority but ultimately fail to upend the gender hierarchy trigger schadenfreude beyond that expected from their wrongdoings. In the end, the stories of Maleficent and Elizabeth Holmes celebrate the downfall of women who brazenly embrace power, without showing women how to challenge the gender hierarchy.