Thomas Gimbrede's engraving served as the principal presidential image of James Monroe, becoming the most widely disseminated image during Monroe's years in office. Artist John Vanderlyn commissioned the print, based on his own painted portrait, in the spring of 1816, when he learned of Monroe's presidential aspirations. The engraving began circulating just after the president's inauguration in March of 1817. Vanderlyn, a houseguest and close friend of the then-secretary of state, had recently finished painting two almost identical portraits of Monroe. James Madison had commissioned the original, which pleased Monroe enough to request another for himself. From Monroe's version, now owned by the National Portrait Gallery, Vanderlyn made a quick sketch to function as the engraver's model. Guided by this drawing, Gimbrede offered the first engraved image of the fifth president in this print.