Many of the songs in Crazy Ex-Girlfriend are framed as perceptions of the events and conversations surrounding the protagonist Rebecca Bunch. Due to her fragmented sense of self and mental health issues, the songs are often fantastical misrepresentations. As Jessie Fillerup has written, the songs allow the audience to share in Rebecca’s subject position and enable the show to create an empathetic portrayal of mental illness. This article incorporates this insight but expands the idea of intersubjectivity to explore the show’s other goals, such as deconstructing the musical and romantic comedy genres. Using Laurent Berlant’s Cruel Optimism (2011), I demonstrate that many of Rebecca’s problems can be attributed not only to her childhood traumas or mental illness but to a misappropriation of musical theater ideals, which have become cruel.

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