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From the beginning of his career, Go Hui-dong suffered from artistic uncertainty. First trained in traditional painting, he became the first pioneer of the new Western painting techniques. Later, he abandoned Western painting, saying, “what is needed today is Eastern (dongyang) painting,” a Japanese-coined term for traditional style painting. “Elegant Gathering,” a painting depicting an evening gathering of the artist and his circle of friends, including the art collector and critic O Se-chang (1864-1953) and the poet and historian Choe Nam-seon (1890-1957), adopts a traditional theme of East Asian literati painting. It appears as a mildly modified version of “elegant gathering” paintings, depicting a group of literati enjoying wine, poetry, and art, in a tastefully arranged setting. A closer look at the painting, however, reveals that the painter has discarded the old stereotypes long used in the elegant gathering theme and has revealed the personality of the participants in a new way. This paper discusses the meaning of such deviation through Go Hui-dong’s lifelong quest for, and often doubt about, the role of the modern artist in Colonial Korea.