This chapter untangles Crazy Ex-Girlfriend’s (The CW 2015–2019) several strands of crudity and overall offensiveness to make the case for the show’s complex commentary on postfeminism and contemporary media culture. Rather than looking at its musical interludes or comic elements as clashing with the show’s exploration of feminist issues, the chapter positions these as essential to the biting critique that has made this portmanteau-hyphen television outlier—a female-lead dramedy-cringe-musical series—a critical, if not commercial success. It outlines the show’s critique of ‘abject postfeminism’, before tracing its rejection of the romanticizing of ‘crazy women’ in US-American popular culture. Exemplary readings of select scenes detail how the series employs different levels of offence to push the limits of female representation in contemporary television.