The artistic patronage among various elites of the Umayyad Dynasty (661-745 C.E.) inaugurated a period of thoughtful and conscientious engagement with the sense of sight in all its aspects. This was a time of active experimentation and innovation in the visual arts which resulted in new thinking regarding the ontological and subjective status of the viewer, the viewed, and the gaze between them. My dissertation examines the art and architecture of this era in three parts. The first addresses the modern reception of this artistic tradition over the course of the 20th century by selecting three events that frame the standard narrative of the field’s beginnings: a 2012 exhibition, “Byzantium and Islam: Age of Transition,” at the Metropolitan Museum of Art, the publication in 1973 of Oleg Grabar’s The Formation of Islamic Art, and the 1903/4 installation of the Mshatta façade in the Kaiser Friedrich Museum in Berlin. The second part is a series of conceptually driven formal analyses of various Umayyad monuments and artworks including the Dome of the Rock, the Great Mosque of Damascus, the Sana’a Qur’an, and Qusayr ‘Amra. These accrete into an understanding of how ‘the viewer’ came to be an embodied subject during this period of artistic creation. The third part examines the various ways in which the relationship between meaning and form came to be constructed and worked through many of the same visual programs discussed in the second part. This process of ‘working through’ meaning and form involved the empowerment of images, a willingness to experiment with them, and to actively play with, undermine, and question the very premises of sight itself.