A decade after the publication of Langston Hughes’s Simple Speaks His Mind (1950) and less than three months before the construction of the Berlin Wall, the German translation, Simple spricht sich aus (1960), was published by Auf-Bau Verlag in the German Democratic Republic. The complex relations between two languages and cultures were further complicated by the radical ideological differences in divided postwar Germany. Almost fifty years after German reunification and the election of the first African American president of the United States, the Austrian Milena Verlag released a new German translation of Simple (2009). Viewing multiple forms of translation, this chapter explores how Hughes’s text meant very different things at different points in Simple’s cultural history. Issues of class and race attained varied interpretations in the different translations studied here, addressing diverse issues over time and place, both separating and uniting content and language.