In popular music studies, androgyny is frequently used to describe a performance that demonstrates a fusion of male and female characteristics. The commitment to the image of the androgyne dominates interpretative strategies, and any discussion of how androgyny might be expressed in a song’s musical elements are orientated around the concept’s visual presence. In this thesis, I develop and apply a practice of ‘listening out’ to androgynous expression in the musical fabric of popular song, and I mobilise this through a comparative analysis of Virginia Woolf’s novel The Waves (1931) and Kate Bush’s song cycle A Sky of Honey (2005). I begin by providing an overview of the study of gender and sex in popular music, before focussing on examples that specifically consider androgyny. Identifying key discourses and methodological approaches I consider the possibilities and limitations in existing strategies. I close the chapter with some preliminary thoughts on how ‘listening out’ can enrich the understanding of androgyny’s expressive capacity. In chapter one, I explore Woolf’s formulation of androgyny as presented in A Room. By surveying critical responses to her formulation, I claim that the textual expression of Woolf’sandrogyny shifts the focus away from the specificity of the sexed/gendered body of the androgyne. I then consider the reception of Bush’s music in academic research, highlighting methodological strategies and her existing connection to androgyny. Drawing parallels between Woolf’s and Bush’s artistic ambitions and their expressions of androgyny, I explore the importance of ekphrastic approaches and musical-theoretical techniques, both for transmedial analysis and the interpretation of androgyny. In chapter two, I begin the comparative analysis of The Waves and A Sky of Honey by examining the creative context surrounding each text. I then explore expressive parallels in form, genre and narrative, before considering how Woolf’s and Bush’s textual representations of pastoral complicates androgyny’s connection to states of nostalgia. In chapter three, I examine the technical expression of characterisation. I argue that the evolving relationship between characters progresses through a state of deconstruction to the disarticulation of ‘I’, and in privileging a choric community reveals the androgynous subject as multiple, fluid and fragmented. The final chapter expands these explorations by examining the material life of androgyny. I mediate this through a study of the revolutionary potential of artistic practice, focussing specifically on the presence of birdsong in both works. Analysing two exceptional moments in A Sky of Honey and recontextualising comparable moments from the final soliloquy of The Waves, I trace the generation and release of androgynous jouissance.