Though generally considered to be the "Father of the Constitution, James Madison, the fourth president of the United States, wasn’t a man of pomp or circumstance. 

Seriously shy, and a bit of a hypochondriac, Madison preferred the company of his books to most people, apart from his wife and political partner Dolley, who was 17 years his junior. They were wed after being introduced by Aaron Burr in Philadelphia in 1794. 

As mentioned, Madison (along with the future star of the musical Hamilton, Alexander Hamilton) played a vital role in the creation of the U.S. Constitution. Before his claim to the presidency, Madison was the Secretary of State to Thomas Jefferson. Influenced by the Enlightenment, Madison put his foot down in regards to State and Church staying separate in the new free world. This is all good and well, but he was decidedly less successful when it came to foreign policy, as he was unable to stop Britain from encroaching on U.S. neutrality. We do have him to thank for the annexation of West Florida. But he also owned hundreds of slaves, despite claiming to believe slavery went against the country's great Revolutionary principles. As with most presidencies, Madison's was a mixed bag, and many of his actions did not age well in the light of progressive history. 

The commission for this painting came from gallery owner John Doggett, who asked Gilbert Stuart to paint the first five presidents in a series of portraits. They are only surviving complete set of portraits depicting the first five presidents of the United States: George Washington, John Adams, Thomas Jefferson, and James Monroe, in addition to Madison. These aren’t the typical flashy political portraits you might recognize from, say, Napoleonic times. They’re simple and subdued, with no overtly patriotic symbols to distract from the serious business of democracy - fitting for a solemn figure like James Madison.