With an off-putting title and a decidedly retrograde premise, the CW dramedy Crazy Ex-Girlfriend is a surprising choice for critical analysis. But, loyal viewers quickly came to appreciate the show’s sharp cultural critique through masterful parody, and this strategy has made it a critical darling and earned it several awards throughout its run. In ways not often seen on traditional network television, the show transcends conventional genre boundaries—the Hollywood musical, the romantic comedy, the music video—while resisting stereotypes associated with contemporary life. The essays in this collection underscore the show’s ability to distinguish itself within the current television market. Focusing on themes of feminism, gender identity, and mental health, contributors explore the ways in which the show challenged viewer expectations, as well as the role television critics play in identifying a show’s “authenticity” or quality.