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In this small half-length self-portrait, Woodville fashions himself as a privileged urban gentleman, in a formal black coat, white shirt with wing collar, and a black bow tie. He has the smooth, broad forehead that contemporaries associated with superior intelligence and virtue; indeed, artist Chester Harding, who founded and guided the Boston Artists Association in the 1840s, was known to have told an aspiring painter he could never succeed "because his head was not big enough." Woodville fixes a penetrating, arrogant gaze on the viewer, embodying the elite social world in which he was raised and which he left behind in choosing the life of an artist. Woodville studied as a private pupil of figure and portrait specialist Carl Friedrich Sohn and throughout his career showed a remarkable capacity for sophisticated depiction of character. The artistic community in which he lived in Düsseldorf was notable for the production of Freundschaftsgalerien, large friendship pictures that gathered small portraits of individual artists. Although none of the American artists were included in these assemblages, Woodville's friend Leutze was a member of the social club known as Malkasten or "Paint Box," where the same artists gathered to eat, socialize, and hold amateur theatrics. Both this self-portrait and the Self-Portrait with Flowered Wallpaper are sophisticated bids at self-representation, which the artist retained in his possession. The painting descended in the family of the artist's second marriage and concealed beneath its canvas an unfinished Portrait of a Woman, that is a likely image of his first wife.