In this piece I have placed Sidney Pointer within the composition because he actively worked to uphold an upstanding representation of the Black Man. He had the opportunity to grow up in the British Caribbean up until around the age of 16. Since he was actually born in Florida he was a citizen and was able to live in America thereby being exposed to both American and Caribbean Black masculinity. Like Douglass he understood the importance of his likeness in media and strove to bear the weight of the respectability of the Black community through the actions of himself as an individual. Amiri Baraka tackled representation within the realm of theater. His brand of Blackness was not so much interested in striving for “White” respectability. In several ways he worked to extend the boundaries confining the Black male in society. Rounding out this visual grounding is Tupac Shakur. He used his expertise as a lyricist, historical studies and lived experience as a young man in the hip hop era to broadcast his understanding of life. He benefited from his predecessors and pushed to live a life free enough to present his own flaws and moments of growth.