This thesis is an exploration of how male trickster figures operate in the Gothic fiction of 20th century American female authors. Specifically, I look at the short stories “The Daemon Lover” by Shirley Jackson, “Good Country People” by Flannery O’Connor, and “Where Are You Going, Where Have You Been?” by Joyce Carol Oates. In each of these stories, a male trickster figure functions as an enforcer of patriarchal standards of women’s roles by punishing those female characters who exist outside prescribed gender boundaries. By writing of the ways in which, and the reasons why, these female characters are punished by male trickster figures, these authors demonstrate the pervasive and oppressive nature of patriarchal systems in Post-World War II United States. The trickster trope is a productive lens through which to view gender politics in these stories and this reading allows for new feminist interpretations of each text