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This essay analyzes the Hyers Sisters, a Reconstruction-era African American sister act, and their radical efforts to transcend social limits of gender, class, and race in their early concert careers and three major productions, Out of Bondage and Peculiar Sam, or The Underground Railroad, two slavery-to-freedom epics, and Urlina, the African Princess, the first known African American play set in Africa. At a time when serious, realistic roles and romantic plotlines featuring black actors were nearly nonexistent due to the country’s appetite for stereotypical caricatures, the Hyers Sisters used gender passing to perform opposite one another as heterosexual lovers in their early operatic concerts and Urlina. Because they were sisters, audiences did not perceive any threat of an actual intimate exchange. As a result, they were able to create respectful depictions of romantic relationships onstage between black men and women that were otherwise impossible. Collaborating with other black theatre artists, including Sam Lucas and Pauline Hopkins, they created productions that presented inspiring depictions of black male heroes, intact black families, and blacks achieving social progress after securing their freedom. The Hyers Sisters’ positive (re)presentations of (African) American life and love were strategic, political acts of resistance against the rampant racism of Reconstruction-era America. Their pioneering productions enabled the sisters to create early opportunities for themselves and other black artists in a white, male dominated industry, and helped lay the groundwork for the growth and development of black theatre and popular entertainment in the decades to come.