This paper explores the link between the improvisatory nature of blues music and resistance to socially prescribed expectations for gender and sexuality in Ann-Marie MacDonald’s first novel, Fall on Your Knees (1996). When Kathleen Piper, one of the main characters in the novel, leaves her home in Cape Breton in1918 to pursue a classical singing career in New York, she finds herself transfixed, and subsequently transformed, by a performance by Jessie Hogan (a fictional character clearly modeled on Bessie Smith), in large part because of her remarkable improvised vocals. Hogan’s performance points to the rich history of the great blues women of this time period, women who, through their songs, costumes, and improvised lyrics and melodies, explicitly and implicitly tackled issues such as domestic violence and poverty, and challenged normative ideas of black female identity and sexual orientation. This history provides a critical context for Kathleen’s growing sense of autonomy and sexual identity, and this paper argues that the representation of Bessie Smith in the novel (in the guise of Hogan) enables possibilities for improvising new social relations and sexual identities.