Clay Cane writes of hip-hop in <em>The Advocate</em>, “one cannot forget its homophobia, a contagious infection in an art form that once stood for positivity.” This reactionary sentiment to hip-hop masculinity implies a sort of cognitive dissonance toward its intersection with queer theory. In line with the thinking of Moya Bailey and Mark Anthony Neal, I contend that hip-hop should be viewed––rather than dismissed––in terms of opportunities to disrupt oppressive structures within the genre. Little scholarship has used this framework to address disruptive performances outside of queer bodies. This paper attempts to fill this gap by analyzing the enigmatic, comical, at times oppressive, works of rapper MF DOOM. I specifically analyze DOOM’s creation and embrace of villainous identities, his subversions of capitalist mentalities in music, and his complex, transgressive sexualities, juxtaposed with the violent homophobia found in his later work. Ultimately, the purpose of this essay is to qualify archetypes of queer disruption in hip-hop, using DOOM as a case study of both transgression and oppression.