Critics have considered the work of Mark Tansey either simplistic or accessible only to viewers with extensive art historical backgrounds. His paintings hang in the best museums of the world, from the Metropolitan Museum of Art to the Museum Moderner Kunst, Vienna. However, an inherent conflict arises. For critics, Tansey must be either accessible or inaccessible, and not both. Yet, Tansey's paintings operate precisely on this edge between the extraordinarily simple and the overwhelmingly complex. To understand the complexities of this dilemma it would be helpful to analyze Tansey's paintings that deal with philosophers and literary critics, which are the most complicated works in his oeuvre. The philosophers included within these paintings are: Roland Barthes, Jean Baudrillard, Harold Bloom, Paul DeMan, Jacques Derrida, Michel Foucault, Geoffrey Hartman, and Jean-Francois Lyotard. All are postmodernists working in opposition to the reductionist rhetoric of mid-twentieth century modernism. This thesis will consider his images of philosophers that include Mont Sainte-Victorie (1987), The Bathers (1987), Derrida Queries DeMan (1990), and Constructing the Grand Canyon (1990) as the confluence and conflict of ideas that deal with words and images.