Due to their historical oppression and limited opportunity, throughout American history, the most recognizable African-American figures in popular culture tend to be from the sporting world or the music industry. African-Americans have played an integral role in the development and popularization of these art forms. Despite their success, they are often used as a representation of their entire race, a role that is exacerbated by the media. In our contemporary society, the media plays a major role in pushing narratives and reinforcing stereotypes through the news that they produce. When it comes to news coverage on African-American athletes and musicians, much of the media coverage tends to utilize problematic rhetoric that reinforces popular negative stereotypes of African-Americans as a whole. This paper will examine three different subjects: the boxing career of Jack Johnson, the development of ragtime and jazz music, and the development of hip-hop music and its impact on the culture of the sporting world in the 21st century. This paper will primarily focus on how the media has represented these popular figures, but will give special attention to the relationship between the two avenues that has developed as a result, arguing that the permeation of hip-hop culture into the sporting world has created a bond that has rendered the two cultures nearly identical.