John Hamilton Mortimer made this etching, Successful Monster, in England in 1778. Mortimer dedicated a series of fifteen etchings to Sir Joshua Reynolds, the first president of the Royal Academy, of which this is one. In it, we see a grotesque, hairy monster with a serpent’s tail abducting a refined woman. With its provocative title, the print wryly suggests the complex, and sometimes monstrous, conditions for success in the art world. Mortimer seems to ask, what kind of behavior does the art world reward? Who benefits when refinement is overtaken by the grotesque? To understand the image, we can start with the dedication to Reynolds, who was a powerful figure in the art establishment. Was Mortimer commenting on the state of the Royal Academy? Further research into the art market in England, the role of institutions, and the relationship between artists can help us to better understand the image. Ultimately, we can see the meaning of art is deeply rooted in its specific context.