The purpose of this study was to understand the symbolic messaging in hip-hop music as it relates to the lived experiences and realities of Black Americans in the United States. The study examined the song and music video titled “The Story of O.J.,” by hip-hop artist Jay-Z to gain a better understanding of how Jay-Z interpreted the impact of Black Americans’ lived experiences in the United States on their identity and ability to progress economically and socially, regardless of social standing, within subcultures such as sport. Employing a content analysis method, data were collected and analyzed using critical race theory. The results of the analysis of lyrical and video data identified three major themes: (a) battle with Blackness, (b) economic enslavement and financial freedom, and (c) systematic subjugation.