Providing a thorough examination of Shirley Clarke's 1963 film The Cool World, this article explores the link between social and cultural alienation and its relation to the racial strive of the 1960s. As such, the author analyzes how Clarke's work connects those themes to her examination of black masculinity. Accordingly, Clarke's film deconstructs masculinity as a whole and exposes it as a societal construct. Nogués also writes about The Cool World and Clarke's other 1960s works generally through the optic of feminism, thereby showing how racism and sexism are intertwined in the white patriarchal order.