In 1741 he was still apprenticed to
Gustavus Hesselius (1682–1755), a Swedish-born painter who resided in Philadelphia. It is probable that he painted the portraits of his brother, George Claypoole Sr. (1706-c1770), and sister-in-law, Hannah Claypoole (ca 1708–1745), as the portraits were in the household of George Claypoole Sr., joiner and cabinetmaker, also shop keeper, Front Street, Philadelphia, Pa. Ca 1770 – portraits inherited by George and Hannah Claypoole's eldest son, George Claypoole Jr., (1733–1793), joiner and cabinet maker, of 65 Walnut Street, Philadelphia, Pa. Ca 1793 – portraits inherited by George Jr. and Mary (Parkhouse) Claypoole's eldest and surviving son, Dr. Willam Claypoole, (1758–1797) of Wilmington, North Carolina. 1797 – portraits inherited by William and Mary (Wright) Claypoole's only surviving child, Ann Grainger Claypoole, (ca 1791–1832) of Wilmington, North Carolina. Owned since 1984 by the Colonial Dames of Wilmington, North Carolina. He had two early students that went on to become well known artists: James Claypoole Jr. (ca 1743–1822), and
Matthew Pratt (1734–1805). He served as High Sheriff of Philadelphia from 1777 to 1780. Commissioned and paid $8 by Captain
Abram Markoe in 1775 to paint a flag for the
Philadelphia Troop of Light Horse. ==Marriages and children==