ABSTRACT In this paper, we analyze the conjuncture framing the recent rise of media representations of female con artists, looking at two recent examples of the trope on television: Inventing Anna (a fictionalized account of con artist Anna Delvey) and The Dropout (a fictionalized account of Theranos founder Elizabeth Holmes). We situate the new visibility of women who lie, scam and cheat on television within a set of distinct yet interlocking cultural anxieties: about the “believability” of women’s speech in the aftermath of the #MeToo movement; about the capacities for inauthenticity, artifice, and deception inherent to digital media culture; about the con logics of contemporary global capitalism; and about the pernicious role that white women’s believability plays within everyday operations of white supremacy in the United States. Read through this lens, the “post-authentic” con woman becomes legible as an ambivalent backlash text: a parable that warns about what happens when (white) women are taken at face value and allocated the benefit of the doubt. In a contemporary popular feminist context where women have been implored to be confident, self-assured, and self-possessed “girlbosses”, shows like Inventing Anna and The Dropout reposition the con(fident) woman as a figure of necessary cultural suspicion.