This chapter examines the song cycle (also thought of as a monodrama or solo opera) by composer William Bolcom and playwright/librettist Sandra Seaton, From the Diary of Sally Hemings. The chapter includes a discussion of the DNA, kinship, and social controversies over the interracial pairing of Jefferson, a founder of the United States as a nation, and Hemings, his slave and consort. Through an analysis of the compositional genesis of the work, the text, and the music, this chapter also explores what is at stake for thinking about the breakdown of black-white racial categories. Extended references are made to Saartijie Baartman (the South African “Hottentot Venus”) and Edward Ball, the descendent of the Ball plantation who looked up interracial relationships with slaves in his family.