John Hesselius was the foremost portraitist in the mid-Atlantic region in the third quarter of the 1700s. One of the earliest native-born American artists, Hesselius was the son of the Swedish artist, Gustavus Hesselius (1682–1755), who settled in America in 1711. Probably born in Philadelphia, John Hesselius painted portraits of the aristocracy of Virginia, Maryland, Delaware, New Jersey, and Philadelphia, primarily between 1749 and 1763, though he is believed to have instructed Charles Wilson Peale and continued to paint portraits sporadically until 1777.

Painted about 1757, the portrait of Anne Lloyd Tilgman and her daughter Anna Maria is one of few existing double portraits painted by Hesselius and is a fine example of the artist's ability to depict rich fabrics using strong color and a complex patterning of highlights. In keeping with Anglo-American portrait traditions of the time, Hesselius adopted the identical pose and setting, in reverse, of Sir Godfrey Kneller’s portrait of Mary Butler (née Somerset), Duchess of Ormonde and her son Thomas, Earl of Ossory, engraved in mezzotint by Robert Williams. Such adaptations would have been viewed as a compliment to the sitter and not a form of plagiarism.

Anna Lloyd Tilghman was born into the prominent Lloyd family of Maryland with several members in politics, including her uncle Edward Lloyd who served as the Colonial Governor of Maryland in the early 1700s. Her daughter Anna Maria later married her cousin Tench Tilghman, who worked as an aide-de-camp to General George Washington. Anne Lloyd Tilghman’s husband, Matthew Tilghman, was a member of a leading family in Chestertown, Maryland, a planter, enslaver, and merchant.