In the early twentieth century, an increasingly diverse group of Russians and Americans reflected upon their changing worlds in literature and visual culture. They produced competing representations of serfs, enslaved African Americans, peasants, and freedpeople that alternately idealized and criticized the pre and post-emancipation eras. This chapter studies the work of Joel Chandler Harris, Thomas Nelson Page, Kate Chopin, Charles Waddell Chesnutt, Thomas Dixon, Jr., W.E.B. Du Bois, Anton Chekhov, and Evgenii Opochinin.