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If moral interpretations are based on the discourse of good, then the concept of evilness, considered as a moral error, must necessarily appear in contrast to the former notion. However, we can yet consider another framework for evil if we focus on the analysis of the villain’s source of wickedness as well as on the effects caused by this evil. Following an ethical and philosophical perspective, we will question the identity of a famous screen character, Regina Giddens (starring Bette Davis) in William Wyler’s film The Little Foxes (1941), as one of the most malevolent, manipulative, selfish, and evil characters of the 1940s Hollywood cinema. Bette Davis’ role was that of a defiant woman with a greedy and venomous nature. Moved by materialistic desires, Regina becomes an unscrupulous woman capable of any and every moral wrong. Still, she is the absolute protagonist of the film and she even leads the audience to sympathize with her powerful (evil) spirit. By offering a portrayal of Regina Giddens, a new woman in the new South, we will comment on woman’s evilness at a very specific time in the past, the Reconstruction period. But we will also prove that she could very well represent the antecedent of the 21st century’s evil woman, as she can also be compared to some classical villainesses. This study will examine Regina’s behavior, both in a social and a moral context, so as to re-interpret her wickedness as a double-edged sword: a powerful tool in her struggle against tradition as well as the cause for family decay and loss.