Controlling images and negative stereotypes have had damaging effects on black men and women. The entertainment industry continues to play a vital role in perpetuating these historically damaging images to people all over the world. Early representations of black men and women within entertainment were performed by white men under the guise of blackface. These representations were offensive and inaccurate portrayals of black life. Early blackface minstrel performances of black women were performed by white men in blackface who were also cross-dressing. Their performances presented black women in stereotypical roles which have become a norm. Recently, there has been a phenomenon of black men cross-dressing as black women portraying negative stereotypes. These depictions done under the guise of comedy further perpetuate controlling images of black women to the world. This research examines how current and former displays of gender minstrelsy manipulate the image of Black womanhood.