||In the 1660s, after the Restoration of Charles II to the throne, female performers acted on stage for the first time, leading to increasingly sexualized female characters and investigations into gender roles. "Breeches" roles, where women cross-dressed, became progressively more popular, with actresses such as Susanna Verbruggen becoming well-known for their ability to play men and sport trousers. Similarly, in the pre-Hays Code films of the ‘30s, female actresses were performing overtly sexualized roles that required them to wear men's clothing. Marlene Dietrich, for instance, was known for her proficiency in playing savvy cabaret performers and donning masculinized attire. Although these time periods are almost 250 years apart, there are many similarities between these portrayals of women and their position in society. These women were sexualized and objectified as images, yet paradoxically maintained a kind of power through their parody of gender roles. This project focuses on Susanna Verbruggen and Marlene Dietrich as emblematic of popular cross-dressing and overtly costumed actresses during the 1690s and 1930s respectively, analyzing their roles, on stage, in film, and in the public eye, to determine whether these women are strengthening or undermining the patriarchal society that surrounds them. In keeping with Judith Butler's notion of gender as performative, these actresses/characters utilized masquerade and parodic elements to demonstrate their ability to "pass" as male, illuminating the constructed nature of gender roles. It seems apparent that these women's parodic portrayals of men are subtle modes of resistance by which they lay bare the gender and patriarchal apparatus of society. Women are often seen as responding to male "cues" and "acting" in conventionally feminine manners. However, in several of these texts, female characters, often in conjunction with their experimentation in masculine and feminine roles, are also seen as providing "cues" for men, instead of passively responding to male prompting. However, it becomes evident that it is not entirely possible for these women to obtain a feminist paradise through donning masculine attire. Their position as cross-dressing women is complicated, because in many instances men have written their hybrid position for them, supporting the Irigarayan view of women as commodities and femininity as an ascribed role. These cross-dressing women/characters are often required to act in sexist ways against others of their gender to gain power and, as a result, could simply be seen as reasserting the status quo.