This article discusses the theatrical practice of women performing traditionally male roles in Shakespeare. Whilst historically the phenomenon is nothing new, since the 1970s the practice has been particularly associated with the politics of feminism. This article proposes to examine this connection in order to explore how far the convention of casting women in the male roles of Shakespeare has been influenced by changing social, political, and cultural discourses. It will do so by considering two specific manifestations of the theatrical practice: firstly, the National Theatre’s 1995/6 Richard II directed by Deborah Warner, in which Fiona Shaw played the eponymous male character and secondly the 2012/13 all-female Julius Caesar, directed by Phyllida Lloyd for the Donmar Warehouse. Moreover, it will locate these two productions, separated by seventeen years and the turn of a century, within their specific historical, theatrical, and theoretical contexts. Through an analysis of the material conditions that gave rise to the contemporary receptions of these two productions, the objective of this article is to draw conclusions concerning the differing ways in which, through casting women in the male roles of Shakespeare, theatre practitioners have created particular theatrical conversations with their audiences.