Benjamin Greenleaf was born in Hull, Massachusetts. He started his career as an itinerant portrait painter as early as 1803, traveling through Maine, New Hampshire, and Massachusetts. His subjects were interrelated by marriage or by community ties and included doctors, clergymen, and military personnel. Greenleaf usually worked with oil on board, but from 1810 to 1818 he also produced reverse paintings on glass.

Both portraits demonstrate typical characteristics of Greenleaf profiles. Most notably, they are three-quarter bust-length portraits that fill most of the support and stand out from their dark backgrounds.