Using historical censorship records, industry publications, and interviews with film raters, this article reveals the evolution of gender bias in film regulation. This article asserts that film ratings in the current era repress images of agentive sexuality and pleasure-seeking for women. First, this article examines cinematic treatment of gender and sexuality during the Hays Code. Next, the transition to film ratings is analyzed with respect to its governing ideology and economic effects. Blue Valentine (2010), Charlie Countryman (2013), and The Cooler (2003) are used as case studies to illustrate film ratings’ regressive management of gender dynamics. Lastly, suggestions for maintaining freedom of expression while ensuring more equitable portrayals of women are proposed.