Jane Gray Otis Prior may have been a boarder at the Misses Martin's School in Portland, Maine, when she painted this mourning piece. Mourning pieces gained favor as schoolgirl exercises in the early years of the nineteenth century, especially after the death of George Washington in 1799. Laden with symbolic imagery, they combined classical funerary elements, inspired by archaeological sites discovered in the middle of the eighteenth century, with Christian ideas of the good garden. Although some mourning pieces commemorated well-known literary and historical figures in the tradition of European antecedents, the art form was democratized in America to include personal tributes to family members or friends. The earliest American mourning pieces were usually needleworks executed in silk embroidery on silk, with watercolor sometimes used in the sky or to paint faces. This example was executed entirely in watercolor and ink on silk but retains the needlework aesthetic in short brushstrokes that simulate stitches.

Jane Prior was one of four sisters of well-known portrait painter William Matthew Prior. Her mourning watercolor memorializes their father, Captain Mathew Prior (1774–1815), and their brother Barker (1799–1815), who were lost at sea. The monument sits in a garden setting with other family stones against a seascape with a departing ship. The text on the stone mourns the loss of these important family members who "sailed from Bath for England...and have never been heard of since." Jane is also known for another schoolgirl exercise, a scenic painting on a box. It is not known when she moved to Richmond, but in 1824, Jane Gray Otis Prior "of Richmond" married Dr. Erastus Willey in St. John's Church in Henrico County, Virginia. Her husband died in 1859 and is buried in the North Church Cemetery, in Henrico County.

Stacy C. Hollander, "Mourning Piece for Captain Mathew Prior and His Son Barker," in American Anthem: Masterworks from the American Folk Art Museum (New York: Harry N. Abrams in association with American Folk Art Museum, 2001), 309.