From its beginnings in 1970’s New York, hip-hop has offered a cultural outlet for disenfranchised communities across the United States and today commands global influence. However, over the course of its evolution, hip-hop has wrestled with notions of masculinity. As its popularity has increased, so has the violent policing of sexuality and gender roles within the culture. Rereading the commercialization of hip hop as the site of a colonial encounter, with capitalism as the force undergirding its entrance into mainstream American consciousness, implications of the institution of violent masculinity and homophobia become readily apparent. With the rapid popularization of gangsta rap music, homosexuality became a marker of inferiority within the culture that coincided with the emergence of a complicated relationship between hip-hop artists and the sexuality they were sworn to disavow. The effective death of homosexuality as an acceptable erotic encounter within hip-hop culture has resulted in the subconscious development of mourning for its loss: a pathological turmoil enunciated within the most homophobic of hip-hop discourse. Analyzing artists’ attempts to fully immerse themselves within this schema of violent masculinity and homophobia allows for the discovery of how this oppressive paradigm can be destroyed from within the genre by those who fully embody these destructive ideologies.