This study concentrates on the misunderstood and maligned figure of the black hustler to re-assess the 1960s constructions of black masculinity as they inform the politics of race and class mobility in the United States during and after the Civil Rights period. Whereas critics such as David Dudley, Lawrence Goodheart, Patrick Daniel Moynihan, and Terri Hume Oliver, amongst others, have read the black street hustler in terms of psychopathology and criminality, I argue that Claude Brown, Malcolm X, and Iceberg Slim enlarge the urban and folkloric roots of the black hustler in order to critique the very foundations of American capitalism itself as well as to challenge the social norms of white middle-class masculinity by mimicking these concepts through hyperbolic performances, which negate both the supposed psychopathology and criminality associated with the black hustler. Although the hustler figure is nearly omnipresent in Claude Brown's Manchild in the Promised Land, Malcolm X's The Autobiography of Malcolm X, and Iceberg Slim's Pimp: The Story of My Life, these selected works tend to be read as autobiographies that rely on conventions of social realism, black nationalism, and/or confessional narratives, focusing exclusively on the negative aspects of the black hustler. Instead, this study claims that the selected texts should be privileged as hustler narratives, drawing attention to the function of the hustler as participating in a wider American tradition of upward class mobility. In the process, the black hustler hyperbolically emulates, criticizes, and rejects or restructures such concepts of individual 'rags-to-riches' capitalism and/or middle class respectability in order to achieve his own status and define his own terms for the construction of alternative black masculinities. Chapter One shows how Brown's Manchild in the Promised Land utilizes the presentation of the hustler to destabilize prevalent articulations of the North as Promised Land in migration narratives and rebuilds community through jazz musicianship and the male-centered community that it creates. Chapter Two posits the hustler in The Autobiography of Malcolm X as a developmental stage that articulates or reproduces itself on the streets, in prison, and within the Nation of Islam and leads Malcolm to an emerging Pan-Africanism through his reliance on, and questioning of, unstable male-centered communities. Chapter Three discusses Iceberg Slim's presentation of the hustler in Pimp: The Story of My Life by highlighting the critical similarities between the pimp and the standard managerial capitalist and reveals how false contrition gains him entry into middle-class status. The Epilogue discusses the work of Nathan McCall and the "strained position of the middle class" as seen through the black male figure, which speaks to the ineffectiveness and lack of functionality that traditional capitalist advancement offers for poor urban settings.