This chapter draws upon iconography, film studies, and semiotics in two examples of electronically mediated masking that intentionally subvert the voyeuristic white gaze. It investigates the descriptions of Lindy Hop in The Autobiography of Malcolm X (1966) and the blackface in Spike Lee’s Bamboozled (2000), which intentionally juxtapose explicitly racist caricature and performative virtuosity, reading those passages for their cultural/political subtextual discussions. It argues that Malcolm X and Spike Lee--as cultural commentators from within the African American community--use dance as a means to problematize the paradox of black creativity’s virtuosity as it has flourished “behind the minstrel mask.”