Note: This work is part of a pair.

Charles Willson Peale was commissioned to paint this remarkable pair of portraits late in 1788 by Christopher Hughes (1744–1824), a native of Ireland who had immigrated to Baltimore during the early 1770s and became a silversmith. Hughes married Peggy Sanderson (1760–1825), also from Ireland, on January 6, 1779, and the couple had seven children; their youngest son Christopher Hughes, Jr. (1786–1849) became a career diplomat who served as secretary to the American peace commissioners at the Treaty of Ghent, Belgium, in 1814. By the time that Peale painted these portraits Hughes had made a fortune in banking and real estate. The artist thus represented him as a gentleman, set in a formal pose before a view of Baltimore harbor holding the English clergyman and poet Edward Young's popular poem The Complaint: or Night-Thoughts on Life, Death & Immortality.

The historian Charles Coleman Sellers considered the considerably less formal double portrait of Peggy Sanderson Hughes and one of her daughters holding a doll as “one of Peale's cleverest compositions.” The girl's identity is uncertain: she is either the Hughes's fourth daughter Peggy (1786–1843), or their fifth daughter Louisa (1787–1861), future wife of Colonel George Armistead, the American hero of the Battle of Baltimore during the War of 1812.