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In this article, an analysis of the pictorial art of Jean-Michel Basquiat is undertaken in a threefold manner. First, Basquiat’s graffiti and street art is understood as a means to confront the norms of the art world. Then, Basquiat’s style and his artistic collaboration with Andy Warhol are questioned as techniques to create, through opposition, new aesthetic norms. A contextualization of Basquiat’s art allows us to better understand the importance of the family dynamic, his drug addiction, and the three severe traumas he suffered in childhood. Finally, two of Basquiat’s paintings, To Repel Ghosts and Eroica, are analyzed as an ultimate transgression fueled by the radicality of Basquiat’s artistic gesture.