The story of Anastasia Nikolaevna Romanova has been engrained in the American imagination for nearly a century. This tale has often been told on stage and screen, depicting Anastasia and her most famous impersonator: Anna Anderson. The adaptation of Anna and Anastasia’s tale that has made the most lasting impact is the 1951 French play, Anastasia, by Marcelle Maurette, and its 1954 English translation by Guy Bolton. Four more adaptations have followed that progenitor play: the 1956 film, Anastasia; the 1965 operetta, Anya; the 1997 animated film, Anastasia; and the 2017 musical, Anastasia. These five artistic adaptations evolved from one another, navigating their own history alongside changing American values. This thesis situates each production within American sociopolitics of the twentieth and twenty-first centuries, revealing how each production is far more indicative of American ideals than Russian history, particularly with regards to immigration, foreign policy, and feminism.