To gesture toward a more watchful, boundless, and accessible approach to art writing, this thesis (1) compares art criticism to art writing, as they both developed in relation to the artworld; (2) contrasts conventional and unconventional theories of art as they have manifested throughout history as constitutive modes of thought that informed the separate but related practices of art criticism and art writing respectively; (3) investigates the issue of gatekeeping, in the artworld, as it relates to the elite subculture of the art market and the inaccessibility of the “art-world ecosystem”; (4) examines the relationship between art and language, in order to understand how it is that artworks and art writing, together and apart, possess the ability to surprise, confuse, and inspire; and (5) looks to the practices of art writers such as Susan Sontag, Wayne Koestenbaum, Cole Swenson, and others, in order to uncover a richer and more generous methodology for writing about art.