This thesis is concerned with establishing a bridge between matters of aesthetics and epistemology, by investigating the mechanisms through which artworks allow agents to derive knowledge through the former’s manipulation. It is proposed that, in order to understand the epistemic potential of artworks, we need to approach them as diagrams, in the sense developed by Charles Peirce. The background upon which the arguments are developed are mainly those of American Pragmatism – with a special emphasis on primary literature from Charles (...) Sanders Peirce about semiotics and inquiry, and John Dewey about aesthetics. It is introduced that the manipulation upon artworks can be an example of an inquiry process, due to artworks’ diagrammatic symbol-type-token structure, which embody the logical relations of abduction, deduction and induction. Through Peirce’s definition of inquiry, and Dewey’s definition of an aesthetic experience, it is possible to defend that artworks deliberate create states of doubt and chance as to stimulate and guide inquiry as a way to achieve an aesthetic experience, corroborating to the claim that inquiry processes and aesthetic experience share the same ontological basis: it is in the nature of aesthetic experience to confront agents and contexts with state of chance and doubt, to be further guided through inference into a state of regularity and belief. In order to develop and test the argument, I present the development of Arthur Danto’s influential theory of aesthetics based on Andy Warhol’s Brillo Boxes, by focusing on a review of Danto’s main writings about it. The central point that Danto developed in this theory is that what gives something the status of an artwork are not the immediately perceivable sensorial features of an artifact, but something else. I claim it to be a “diagrammatic structure” that can be potentially manipulated through an inquiry process. I conclude by establishing a possible development of my argument in relation to modelling processes: as diagrams, artworks can be understood as models, opening room for the emergence of new hypothesis and conjectures about the relationship between aesthetics and epistemology. (shrink)