By 1774, Earl was already working as a portrait painter in New Haven, Connecticut. During the same year, he returned to Leicester in order to marry his cousin, Sarah Gates, their daughter Phebe was born a few months later. Earl would leave them both with Sarah’s parents so he could return to New Haven and continue to paint portraits. Both his wife and daughter joined him in New Haven, living together until their second child, John, was born. Sarah later would attest that this brief six month period was the only time they kept the family together.
Like several colonial craftsmen, Earl was a self-taught artist and an itinerant painter for many years. In 1775, Earl visited Lexington and Concord, where he recently took place one of the first military engagements of the American Revolution. He drew four battle scenes in collaboration with Amos Doolittle, which would later be made into pro-Revolutionary propaganda. Earl himself was a Loyalist to the British crown, even though his father was a Revolutionary Army colonel.
In 1778, in order to escape to England, Earl disguised himself as a servant of a British army captain, leaving behind his wife and daughter. In London, Earl entered Benjamin West’s studio, where he portrayed the King and many other distinguished members of society. Earl moved to the city of Norwich, where he continued to paint portraits and where he married Ann Whiteside, despite never putting an end to his first marriage with Sarah Gates. By 1786, Earl would return to the United States along with his new wife.
Back to the United States, Earl made portraits of notable people such as Roger Sherman, Governor Caleb Strong, Timothy Dwight, among others, as well as a large picture depicting the Niagara Falls. He was imprisoned in 1786, due to his noncompliance to his personal debts. Even in jail, Earl drew portraits of his visitors, family, and friends. He was released two years later.
His son, Ralph Eleaser Whiteside Earl, would also become a painter, which he probably taught. Ralph was considered a “court painter” of President Andrew Jackson. Earl may have also influenced his nephew Augustus Earle, who was noted as the first European artist to travel through all five continents. Earl’s brother James was also a portrait painter.