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Despite its progressive discussion of mental health, gender, and politics, CRAZY EX-GIRLFRIEND has a complicated relationship with Jewishness. The series endorses the Jewish Mother and Jewish American Princess stereotypes through its depiction of the two Jewish female antagonists as one-dimensional caricatures that embody a Philip Roth-inspired, mid-twentieth century understanding of Jewish femininity. While the protagonist, Rebecca Bunch, does embody many characteristics of what Nathan Abrams defines as the “New Jewess with Attitude,” the series’ overt implication that her mental health struggles result from her genetic “Jewish suffering” suggests that her professional and personal successes occur in spite of her Jewishness. Analyzing pertinent scenes and musical numbers, I argue that CRAZY EX-GIRLFRIEND is myopic in its portrayal of Jewish femininity, simultaneously embracing the stereotypes that Riv-Ellen Prell discusses as having come to define the mainstream cultural representation of Jewish women and introducing a new paradigm that connects Jewish femininity with psychosis.