Blackface minstrelsy, the nineteenth-century performance practice in which ideas and images of blackness were constructed and theatricalized by and for whites, continues to permeate contemporary popular music and its audience. Harriet J. Manning argues that this legacy is nowhere more evident than with Michael Jackson in whom minstrelsy’s gestures and tropes are embedded. During the nineteenth century, blackface minstrelsy held together a multitude of meanings and when black entertainers took to the stage this complexity was compounded: minstrelsy became an arena in which black stereotypes were at once enforced and critiqued. This body of contradiction behind the blackface mask provides an effective approach to try and understand Jackson, a cultural figure about whom more questions than answers have been generated. Symbolized by his own whiteface mask, Jackson was at once ‘raced’ and raceless and this ambiguity allowed him to serve a whole host of others’ needs – a function of the mask that has run long and deep through its tortuous history. Indeed, Manning argues that minstrelsy’s assumptions and uses have been fundamental to the troubles and controversies with which Jackson was beset.