Undoubtedly, racism is a deeply-anchored problem that continues to vex our world. There is a long history behind it, which can easily be traced back to the Middle Ages and beyond. This article, however, takes into consideration a number of medieval narratives and art works in which surprisingly positive images of Blacks are provided. The encounter with black-skinned people tended to create problems even for the best-intended white intellectuals or poets during the pre-modern era, but the examples studied here reveal that long before the modern age there was already an alternative discourse to embrace at least individual Blacks as equals within the courtly and the religious context. Since Europe did not yet know the large-scale form of slavery, as it emerged in the sixteenth and seventeenth centuries, there were much less contacts between Blacks and Whites. Nevertheless, the evidence brought to the table here clearly signals that we would commit a serious mistake by equating modern-day racism with the situation in the Middle Ages, as much as modern research (Heng) has argued along those lines. It would be more appropriate to talk about the encounter of races within the literary and art-historical context. Even the notion of Black diaspora would not fully address the issue because the evidence brought to the table here engages mostly with black or half-black knights and other individuals who enjoy considerable respect and appear to be integral members of courtly society both in the East and in the West. Instead of working with theoretical models developed for the analysis of racism in our own times, such as Critical Race Theory (CRT), this study offers close readings of literary examples of personal encounters between members of different races in medieval German and Dutch literature, and of the representation of Blacks in late medieval and early modern art history, concluding with some comments on the first Black philosopher in eighteenth-century Germany.