Thomas Jefferson by Mather Brown: Token of a troubled bromance.  

Thomas Jefferson commissioned this for a portrait exchange with his buddy John Adams. Jefferson and Adams were kind of like the Obama and Hillary of their time. Jefferson was a handsome young golden boy. Adams was an unglamorous, hard-working buzzkill who received little thanks for his lifetime of public service. Their contrasting personalities came to a head in the bitter presidential campaign of 1800, in which Jefferson emerged victorious. But they deeply respected each other and famously died on the same day: the Fourth of July.

This is also the earliest known portrait of Jefferson, painted in 1786 when he was in his early ‘40s while he was kicking ass as the ambassador to France. However, Abigail Adams’ letters refer to a mysterious earlier portrait which has since been lost. Some believe that the French artist Nicolas Benjamin Delapierre’s unidentified Portrait of a Seated Gentlemen is the missing Jefferson Portrait.

These were formative years for Jeff. The American Revolution was behind him, but he had the difficult task of maintaining peace in the years leading up to the French Revolution. He was caught in a crossroads of history, and a crossroads of relationships. His wife Martha had recently died. He was smitten with the gorgeous European artist Maria Cosway (a married woman), but also started sleeping with his teenaged slave Sally Hemings (his wife’s half sister) around the same time.

Jefferson was a man of contradictions; a man who wrote in the Declaration of Independence, “...all men are created equal,” but owned slaves; who wrote that blacks were inferior to whites in sensitivity and beauty, yet shared 40 years and at least 6 children with a mixed-race black woman. While his relationship with Hemings seems to have been a loving and committed union, one cannot discount the exploitative nature of sleeping with an enslaved (not to mention juvenile) person. Tellingly, Jefferson freed their children, but never released Sally from bondage even upon his death. In his defense, Jefferson attempted to end slavery from the outset of the American Revolution, but was rejected to appease the Southern colonies.

Thomas Jefferson considered his presidency a failed experiment, but we owe him two big things. He nearly doubled the size of the United States when he sneakily made the Louisiana Purchase without the approval of the federal government, because Napoleon was strapped for cash and was selling it off dirt cheap. He also totally kicked the ass of the Tripoli pirates who were then terrorizing the American shipping industry, hence the “shores of Tripoli” part of the Marine Hymn.

As one of our most influential and better looking founding fathers, Jefferson has been featured on stage and screen countless times.  Among his more notable appearances are the Broadway musicals Hamilton and 1776, and films Jefferson in Paris starring Nick Nolte, and Sally Hemings: An American Scandal featuring Sam Neill. The latter two depict his affair with Hemings.