Robert Hemings was the son of Elizabeth Hemings and, allegedly, John Wayles, Thomas Jefferson's father-in-law. In 1774, when Jefferson inherited the Hemings family and other slaves from Wayles’s estate, he replaced Jupiter as Jefferson's personal attendant. In this role, he traveled extensively, accompanying his master to Philadelphia, Annapolis, Richmond, and Williamsburg. When Jefferson went to France in 1784, Hemings remained in Virginia, hiring himself out as a manservant and keeping his wages for himself.
In his travels, Hemings met an enslaved woman Dolly, who became his wife. In 1794, wishing to live with his wife and children, who belonged to a physician in Richmond, Hemings made an arrangement to purchase his own freedom. The doctor advanced the purchase money, which Hemings repaid in service. He had become free by 1799 and lived with his family in Richmond, where he worked as a fruit seller and possibly carriage driver and owned his own residence.