Dolley Madison was one of the most famous first ladies in U.S. history. She served as White House hostess for two presidents: her husband, James Madison, and Thomas Jefferson, a widower. James Madison was secretary of state in the previous Jefferson administration. Dolley Madison was known for her graciousness and charm, and for her ability to entertain guests and preside at state dinners. When the British invaded Washington in 1814, she escaped to Virginia with important state papers, a Gilbert Stuart portrait of George Washington, and other valuables.

This stamp design was one of only two stamps produced in an extremely small size. In an effort to conserve resources, the postal service conceived a stamp size that provided 150 stamps to the normal pane size rather than the previous maximum of 100. An early regional test led to this smaller stamp size, which did not meet with favor among the stamp-using public. The smaller stamp size was not continued.