The chapter queries theatre-migration through the lens of colonialism and empire. It focuses on two performance repertoires in the former colony of German South-West Africa that reveal the extent to which discourses on migration and citizenship were entangled in debates about ‘race’ in imperial Germany: the German colonial settlers regularly organised theatre and literary societies in the service of empire in the late nineteenth century, while the so-called Cape workers, a large group of African labour migrants from the neighbouring British Cape colony who came to work in the diamond mines of the colony at the beginning of the twentieth century, regularly staged performance events that challenged the strict racial-segregation laws in place under German colonial rule.