Depicts Dolley Madison on the ground of the Montpelier estate. A bouquet of her favourite cape jasmine flowers and the ice house frame the image. The design was based on a portrait of Dolley Madison by Gilbert Stuart. Obverse inscriptions include “Liberty”, “In God We Trust”, “Dolley Madison”, and the date “1999”.

Dolley Todd Madison (née Payne; 1768–1849) was the wife of James Madison, the fourth president of the United States from 1809 to 1817. She was noted for holding Washington social functions in which she invited members of both political parties, essentially spearheading the concept of bipartisan cooperation. Previously, founders such as Thomas Jefferson would only meet with members of one party at a time, and politics could often be a violent affair resulting in physical altercations and even duels. Madison helped to create the idea that members of each party could amicably socialize, network, and negotiate with each other without violence. By innovating political institutions as the wife of James Madison, Dolley Madison did much to define the role of the President's spouse, known only much later by the title first lady—a function she had sometimes performed earlier for the widowed Thomas Jefferson.

Dolley also helped to furnish the newly constructed White House. When the British set fire to it in 1814, she was credited with saving the classic portrait of George Washington; she directed her personal slave Paul Jennings to save it. In widowhood, she often lived in poverty aggravated by her son John Payne Todd's alcoholism and mismanagement of their Montpelier plantation. To relieve her debts, she sold off the plantation, its remaining slaves, and her late husband's papers.

Modelling: James T. Ferrell

Depicts a view of Montpelier with landscaping. The inscriptions include “United States of America”, “Montpelier”, and “One Dollar”.

Modelling: Thomas D. Rogers, Sr.