During the ragtime craze at the turn of the twentieth century, the popular repertoire of “coon songs” was coupled with a robust style of vocal delivery called “coon shouting.” This vocal technique was associated with white women—the most famous “coon shouters” of the day—who, like the performers of the nineteenth-century minstrel show, claimed to have studied so-called authentic Black performance in order to replicate it on stage. Performing the “coon song” repertoire, these women sang, often from a Black male protagonist's point of view, about the trials and tribulations of Black life and romance. How did the dynamics of race, gender, and sexuality in this repertoire change when it was performed by Black women? This article addresses this question by examining caricatures of Black womanhood within the “coon song” genre and by exploring the phenomenon of Black women performing the “coon song” repertoire, using the career of vaudeville performer Dora Dean (1872–1949) as a case study. I track Dean's participation in the “coon song” craze through an archival survey of sheet music and newspaper reviews dating from the height of her career (ca. 1896–1914). Using these sources, I explore the recurring theme of racial passing and the ubiquity of caricatures derived from blackface minstrelsy within Dean's “coon song” repertoire. I argue that Dean successfully navigated stereotypes of Black women's femininity, sexuality, and morality in her performances of “coon songs” and, in the process, subverted stereotypes of Black life, romance, and vocal sound.