|The leading painter in nineteenth-century Shanghai, Ren Bonian (1840–1895) was known for his tour-de-force technique, as well as the remarkable range of subjects he painted. His portraiture, however, occupies a special place in his oeuvre. in high demand but difficult to obtain, these works by Ren focused almost exclusively on denizens of the Shanghai art world. Though much admired, little research has been done on this unprecedented series of images of fellow painters, calligraphers, dealers and collectors. By employing the portraits as documents, and also by using contemporary primary sources such as guidebooks, newspapers, magazines and collected writings by the sitters themselves, this dissertation casts light on Shanghai's little-understood art world, specifically in its social and economic contexts. Thus, this dissertation not only examines Ren Bonian's portraiture practices and strategies, it is also a study of the artist and the art world that engendered these portraits. The dissertation begins with a double portrait of the artist himself. A major obstacle in approaching Ren Bonian is the large number of anecdotes and stories surrounding the artist since his death in 1895. While these largely fictive tales complicate a straightforward biography, they are valuable for understanding changing attitudes towards and assumptions about Ren Bonian. These stories are contrasted with an account of the artist's early career as told through the numerous portraits dating from this period, and with the young artist's rising reputation as documented in contemporary Shanghai guidebooks and magazines. The critical setting of Shanghai is given wider scope in a study focusing on art world business practices and activities using advertisements and articles from the famous Shanghai newspaper, Shenbao. These documents make the increasing professionalization of the artist especially clear, a necessity in Shanghai's marketplace society. The final section of the dissertation looks at Ren Bonian's portraiture as a social practice, both in terms of analyzing Ren's social characterization of his sitters as latter-day literati and in terms of the uses of the portraits as tools of social interaction and identity.