The Vimalakirti Sutra is one of the classics of early Indian Mahayana Buddhism. The sutra narrates that Vimalakirti, an enlightened layman, once made it appear as if he were sick so that he could demonstrate the Law of Mahayana Buddhism to various figures coming to inquire about his illness. This dissertation studies representations of The Vimalakirti Sutra in Chinese painting from the fourth to the nineteenth centuries to explore how visualizations of the same text could vary in different periods of time in light of specific artistic, social and religious contexts. In this project, about forty artists who have been recorded representing the sutra in traditional Chinese art criticism and catalogues are identified and discussed in a single study for the first time. A parallel study of recorded paintings and some extant ones of the same period includes six aspects: text content represented, mode of representation, iconography, geographical location, format, and identity of the painter. This systematic examination reveals that two main representational modes have formed in the Six Dynasties period (220-589): depictions of the Great Layman as a single image created by Gu Kaizhi, and narrative illustrations of the sutra initiated by Yuan Qian and his teacher Lu Tanwei. The latter mode, which became more popular than the former in the Tang Dynasty (618-907), experienced adaptation from handscroll to panoramic mural. It is also during this period that a minor scenario, the Heavenly Maiden Scattering Flowers, became a necessary vignette for representation of the sutra. Since the Song Dynasty (960-1279), the Heavenly Maiden Scattering Flowers gradually became an independent theme. This author investigates the thematic shift caused by various factors. These include the transformation of later Chinese narrative painting and the prevalence of shinu hua 仕女畫, painting of beauties, in later Chinese painting. There is also a change in the role of the Heavenly Maiden from one of many maidens to the only and necessary partner of Vimalakirti. Ultimately, the image of the Heavenly Maiden evolves from a Buddhist heavenly being to a Daoist fairy and later to a symbol representing auspicious meanings.