This dissertation focuses on the relation between art and notions of individual and collective identity, or subjectivity, in the philosophy of G.W.F. Hegel (1770 - 1831). Specifically, it addresses the disputed significance of the subject in relation to the purpose, value, and meaning of artworks central to Hegel's philosophy of art. Numerous critics have readily dismissed Hegel's aesthetic theory as a crude attempt to understand art by way of an arcane metaphysics that undervalues individual agency. Meanwhile, modern Hegelians, such as Theodor Adorno and Arthur Danto, view the so-called 'end of art' thesis in Hegel as a welcome shift in emphasis toward the content or meaning of artworks, but have done little to quell the concern that Hegel's aesthetics marginalizes the role of the subject. By contrast, this dissertation re-examines Hegel's philosophy of art through an in-depth analysis of what we might call 'aesthetic subjectivity' - the status of the individual subject in the context of aesthetic theory - that is overlooked by opponents and proponents of Hegel alike. Focusing primarily on Hegel's oft-neglected Lectures on Aesthetics, this dissertation identifies three distinct aspects of aesthetic subjectivity: aesthetic experience, aesthetic freedom, and aesthetic imagination (both creative and interpretive). A closer look at the development of these categories in the Aesthetics challenges the standard profile of Hegel's philosophy in three ways. First, it reveals a more constitutive role of subjectivity within the broader canon of Hegel's thought, and does so with a level of clarity and concreteness absent in many of the earlier, better-known works. Second, it blurs the standard dichotomy between 'subjectivist' and 'objectivist' aesthetic theories: Hegel's philosophy of art begins as an internal, dialectical development of core aesthetic doctrines in Kant, such as purposiveness, disinterestedness, imagination, and artistic genius. This continuity thesis in turn provides a more nuanced historical analysis of Hegel's relation to 19th century German romanticism, including Goethe, Schiller, and Friedrich Schlegel. Finally, a new theory of aesthetic subjectivity in Hegel offers a timely and much-needed alternative to the postmodern emphasis on the 'negativity' of art, focusing instead on art's potential to offer a positive form of social and political dialogue.