This chapter examines the lives and careers of Dolores “Lola” and Carlota Millanes, Spanish sisters who migrated throughout the Americas in the late nineteenth and early twentieth centuries. Drawing from playscripts, newspaper, and magazine articles, this chapter pieces together their story, one which reflected transformations of entertainment in the Americas. Lola and Carlota led spectacular lives, evidencing remarkable agency to serve as cultural diplomats, to make their own business decisions, and to head acting companies and even families, rare for women of the era. They were also privileged by an imperial system of race and ethnicity that placed whiteness at the apex of a racial hierarchy. Lola and Carlota refashioned conceptions of work, motherhood, and national identity from Barcelona to Buenos Aires and beyond.