This research explored Dunbar’s concept of the mask in order to examine why select black male actors, Flip Wilson (as Geraldine), Eddie Murphy (as Rasputia), Martin Lawrence (as Sheneneh), and Tyler Perry (as Madea), have worn the mask of femininity to survive the vicissitudes of the American stage. It explained what factors compelled these selected black male actors to mask their appearance and why the outward signs of femininity are used as vehicles of communication in their artistic expression. The methodology involved a visual deconstruction of media utilizing literary texts as the instrument to analyze the movies and television shows of these actors, and the research centered on the theories of W. E. B. Du Bois’ notions of the veil and double consciousness, Stephen Greenblatt’s idea of self-fashioning and self cancellation, and Franz Fanon’s views on language found in the book Black Skin White Masks. While wearing the mask, Wilson, Murphy, Lawrence, and Perry challenge society’s notion of black manhood, the limitation of the black man’s freedom of speech, and the role of black women in their plight for an uninhibited existence. These actors also tackle crucial matters, namely black female sexuality, classism, obesity, and the black family. These actors achieve their objective and combat the gaze of both black and white America by self-fashioning and self-canceling their identities at will.