Though born in Philadelphia, Henry Benbridge's career flourished in the South where he fulfilled portrait commissions for distinguished citizens and society families. Formally educated at the Philadelphia Academy, Benbridge also received early artistic training in his hometown, studying with the English portraitist John Wollaston. In 1764, having reached his majority, he moved to Rome to continue his artistic pursuits. He launched his formal career in London in 1769, where he exhibited two paintings at the 1770 Royal Academy Exhibition, including a portrait of Benjamin Franklin, who was then residing in that city. Benbridge returned to Philadelphia in 1770, carrying with him letters of introduction from both Franklin and the noted artist Benjamin West.

In 1771, Benbridge moved with his wife Hetty Sage, a miniature painter, to Charleston, South Carolina. Wealthy Southern families often emulated their English cousins by commissioning fashionable portraits from leading artists, and prominent families from across South Carolina and Georgia kept Benbridge in high demand in the years before and after the American Revolution. This painting of the Archibald Bulloch family of Savannah, executed in a Roccoco manner and exuding an aristocratic air, is representative of the artist's formal conversation portraits. An early leader of the Liberty Party in Georgia, Archibald Bulloch served as president of the Georgia provincial congress and commander-in-chief of the revolutionary state.

A colonial sympathizer, Benbridge was briefly imprisoned following the 1780 fall of Charleston to the British. By 1784, he was actively painting again in Charleston. The final two decades leading up to Benbridge's 1812 death in Philadelphia are relatively obscure, though he did work and teach in Norfolk, Virginia, giving lessons to Thomas Sully, among others.

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