Now relatively obscure figures in the annals of African American theater, Orpheus McAdoo and his wife Mattie Allen McAdoo were once international stars. In the 1880s and 1890s, they led troupes of African American performers throughout the British Isles, South Africa, Australia, and New Zealand. Their ability to meld the staid gospel tradition of the Fisk Jubilee singers with the comic irreverence of blackface minstrelsy appealed to audiences across racial and national lines. In tracing the McAdoos' extensive career, I explore the global history of minstrelsy as both a white supremacist entertainment and an expression of nonwhite resistance. The McAdoos came of age when minstrelsy was gaining worldwide popularity. This white American tradition of blackface performance owed its farreaching success to widespread white anxieties about the political, economic, and social implications of slave emancipation, imperial expansion, and urban industrialism. In the decades after the Civil War, the McAdoos and other African American entertainers confronted and confounded the racist stereotypes disseminated by white blackface performers. These artists carefully engineered their songs and plays to speak back to dominant ideas of race, in necessarily veiled ways. Thus, their performances provided an important cultural space for the negotiation of black and anticolonial alliances across national borders. Overall, this transnational history obliges us to think beyond the often stagnant, domestic political debates over race (and the post-racial) by highlighting the fundamental relation between the rise of a global color line and the expansion of Western modernity. Even in the twenty-first century, minstrel stereotypes continue to haunt us as enduring and adaptive constructions in the discursive fight over the racial status quo.