Benjamin Waterhouse (17541846) and Stuart developed a close boyhood friendship based on their mutual talent for drawing. Stuart began painting, and Waterhouse decided on a career in medicine. He would later be a founder of the Harvard Medical School, maintain a private practice, and, by far his greatest accomplishment, introduce the smallpox vaccine to America in 1800. Stuart painted this portrait in Newport just before Waterhouse departed for medical school in England and Scotland. He studied Waterhouse's face to a degree unprecedented in his previous work, conveying varying flesh tones and the piercing eyes that suggest the vitality Stuart would henceforth bring to his portraits.