Despite extensive research completed on gender and sexuality in music, the theme of prostitution on stage has remained hidden from serious musical scholarship. In this dissertation an exploration of the theme will take place in selected works of Kurt Weill and Bertolt Brecht, regarding the leading female figure of their works - Lotte Lenya. In an attempt to address this theme within specific confinements, this thesis engages in a scholarly and critical examination of selected songs from the collaborative work of Weill and Brecht. An investigation of these works will help uncover societies attitudes towards prostitution at this time and show how this theme was portrayed on stage. It will also consider what impact Lenya’s personal past had on the portrayal of these roles. In response to recent academic writing on this subject this thesis will raise issues of the personification of female characters in Weill/Brecht works, and also tackle the issues surrounding that of the female sexualized protagonist. It will emphasize the importance Lenya had on the work of these two collaborators and examine her role within the politicized literature and drama of Brecht at this time, considering, in particular, his views of what theatre should portray to audiences, and how it should be consumed.