This chapter investigates the figure of the facially tattooed white sailor in colonial literature from the time of the Spanish conquista to the nineteenth century, arguing that facial tattoos were regarded as breaking a taboo: a conspicious sign of alienation from Western society and its norms, they clearly identified those who bore them as “cultural defectors” who were literally marked by non-Western cultures. The taboo of facial tattooing can be traced to the very beginnings of modern colonialism. Early accounts of the conquest of Mexico relate the exceptional case of Gonzalo Guerrero, a shipwrecked sailor who became the military commander of a Mayan chief in Yucatán. When Cortés reached the region and ordered the Spaniard to join his troops, Guerrero refused, reportedly explaining that his countrymen would not tolerate his “carved” – that is, tattooed – face. After the discovery of Polynesian all-over tattooing in the context of the Pacific encounter, the figure of the facially tattooed Westerner became more prominent. Although the practice of tattooing spread among sailors in the nineteenth century, it was usually confined to the arms, so that the taboo of facial tattooing remained in place. Facially tattooed sailors who returned home – such as the Frenchman Jean-Baptiste Cabri – were reduced to the status of freaks, which is why Herman Melville’s "Typee: A Peep at Polynesian Life" (1846) presents facial tattooing as the ultimate threat to one’s social identity: in this fictional text, having one’s face tattooed is equivalent to losing one’s face. Thus, the Marquesan practice of all-over tattooing indicates the limits of the process of cross-cultural exchange that has otherwise characterized the history of tattooing since Cook’s first voyage of discovery.