Bert Williams—a Black man forced to perform in blackface who challenged the stereotypes of minstrelsy. Eva Tanguay—an entertainer with the signature song “I Don’t Care” who flouted the rules of propriety to redefine womanhood for the modern age. Julian Eltinge—a female impersonator who entranced and unnerved audiences by embodying the feminine ideal Tanguay rejected. At the turn of the twentieth century, they became three of the most provocative and popular performers in vaud