John Hesselius (1728/29–1778) was one of the most successful of the colonial painters to train and practice entirely in America. Born the year that his father, painter Gustavus Hesselius moved from Maryland to Philadelphia, John Hesselius undoubtedly was trained as a painter by his father. John also learned from the example of the painter Robert Feke who was in Philadelphia in the late 1740s. Hesselius's first paintings date to 1750. After a period as an itinerant portrait painter in Virginia, Delaware, New Jersey, and Philadelphia, Hesselius settled in Maryland by 1758 where he enjoyed a substantial career as a portrait painter. It was at this time that the stylistic influence of Feke disappeared and Hesselius's work began to reflect the influences of the English-trained John Wollaston, particularly in the characteristic almond-shaped eyes and the puffy cheeks. Hesselius's marriage in 1763 to the widow Mary Young Woodward, who brought with her wealth and land, assured the artist a place in Maryland society. As Wayne Craven has pointed out in Colonial American Portraiture, "John Hesselius could portray Virginia and Maryland planters with conviction because he was one of them." The catalogue of Hesselius's portraits painted between his arrival in Maryland in 1759 and his death in 1774 reads like a Who's Who of Maryland: Calvert, Chew, Hansen--and Addison. The Hesselius and Addison families subsequently were joined when the artist's daughter, Elizabeth, married Reverend Walter Dulany Addison in 1792.

Hesselius painted the portrait of Eleanor Addison, daughter of Reverend Henry Addison and Rachael Dulany Addison, prior to 1775 when she would have been fifteen or sixteen. The delicate flower which she holds in her right hand symbolizes her unmarried state. Addison family letters tell of a total of six portraits in family ownership in the 1940s. Three-Thomas Addison by Gustavus Hesselius, Margaret Dulany Murdock by John Wollaston, and this one of Eleanor Addison--are now in the museum's collection. Three are as yet unlocated: Reverend Henry Addison; Rachael Dulany Addison, wife of Henry; and Anthony Addison, Henry's son and brother of Eleanor. It is probable that Reverend Henry and Anthony were painted by John Hesselius at the same time that he did the portrait of Eleanor. Letters from Reverend Henry to his third son in London mention frames for the six portraits and talk of sending the portrait of Eleanor to England to have a miniature made from it. Apparently he suggested changing the colors of the dress which he claimed "are a little gawdy."