Hip-hop culture is structured around key representational elements, each of which is underpinned by the holistic element of knowledge. Hip-hop emerged as a cultural counter position to the socio-politics of the urban condition in 1970s New York City, fuelled by destitution, contextual displacement, and the cultural values of non-white diaspora. Graffiti (as the primary form of hip-hop expression) began as a political act before morphing into an artform which visually supported the music and dance elements of hip-hop. The emerging synergies graffiti shared with the practices of DJing, rap, and B-boying (breakdancing) forged a new form of art which challenged the cultural capital of music and visual and sonic arts. This article explores moments of intertextuality between visual and sonic metaphors in hip-hop culture and the canon of fine art. The tropes of Michelangelo, Warhol, Monet, and O’Keefe are interrogated through the lyrics of Melle Mel, LL Cool J, Rakim, Felt, Action Bronson, Homeboy Sandman and Aesop Rock to reveal hip-hop’s multifarious intertextuality. In conclusion, the article contests the fallacy of hip-hop as mainstream and lowbrow culture and affirms that the use of fine art tropes in hip-hop narratives builds a critical relationship between the previously disparate cultural values of hip-hop and fine art, and challenges conventions of the class system.