In my presentation, I will focus on the television series Mad Men and on how the show’s textual strategies, together with notions of artificiality and nostalgia, complicate the representation of Fifties’ gender politics. Often praised for its ‘authenticity’ and attention to detail in reproducing the past, Mad Men appears to be quite concerned with the visual aspects that characterize the Fifties. By setting its main narrative in the world of advertising, the show directly deals with questions of images and artificiality, as well as with the awareness of the Fifties as a cultural construct in particular. Aware of its own fictionality, Mad Men is able to engage social, cultural, and political issues crucial for that era to freely criticize the rampant sexism and racism pervading the US at that time, and ultimately to expose the mythical decade of the Fifties as being purely constructed. However, the show also employs textual strategies that undercut its critical approach to the Fifties’ politics. In fact, through the use of the conventions of melodrama, Mad Men often recurs to stereotypical characters, emotional situations, and superficial narrative developments that allow the audience to revel in the nostalgic appeal of the Fifties, despite their clearly fictional nature. By considering both the show’s self-reflexivity and its use of nostalgia, I analyze how Mad Men deals with the representation of gender politics in light of its ambivalent approach to the Fifties. Specifically, I will argue that, by dwelling on a nostalgic portrayal of gender dynamics, Mad Men ultimately undermines its critical potential towards the Fifties and, with it, limits its engagement with the gender politics of that era.