Aesthetic judgments are “dangerous undertakings” for courts, but they are unavoidable in copyright law. In theory, copyright does not distinguish between works on the basis of aesthetic values or merit (or lack thereof), and courts often go to great lengths to try to avoid artistic judgments. In practice, however, implicit aesthetic criteria are deeply embedded throughout copyright case law. The questions “What is art?” and “How should it be interpreted?” are inextricably linked to the questions “What does copyright protect?,” “Who is an author?,” “What is misappropriation?,” and many other issues essential to copyright. Although courts rarely (if ever) explicitly adhere to aesthetic principles in their decisions, the judicial logic used in copyright cases closely mirrors three major aesthetic theories: Formalism, Intentionalism, and Reader-Response. Unfortunately for courts, these theories are largely incompatible. Furthermore, none are sufficiently expansive to cover the variety of practices contained within a single artistic tradition, let alone the panoply of expressive mediums protected by copyright law. As a result, doctrinal inconsistencies abound (both inter- and intra-circuit), and the case law largely fails to provide clear guidance as to the scope of protection—and risk of liability—associated with different artistic practices. This Article examines how courts have applied aesthetic theories to resolve doctrinal issues concerning copyright eligibility, derivative works, useful articles, and statutory fair use. Based on this analysis, this Article argues that courts should adopt a uniform approach to aesthetic judgments from the perspective of a hypothetical “Community of Practice” capable of situating an expressive work in a specific artistic context.