This research aims at studying the representation of African American masculinity in Gloria Naylor's The Men of Brewster Place (1998). Through this study, the researcher provides an overview of the devastating impact of the racial stereotypes imposed on Black men since the early days of enslavement and elaborates how these stereotypes deny Black men full access to the socially constructed ideal image of manhood. Studies about the current crisis of African American males relate problems such as high rates of unemployment, criminality, poor education, conflictual family relations between Black men and women to these racial stereotypes, the legacy of slavery, and institutional racism against Black males. The study also discusses the strategies that can be used by African American men to revise and defy the dominant racial stereotypes imposed on them and how they can reclaim and reform their version of masculinity outside of the paradigm of traditional hegemonic masculinity.