Early Years

Robert Bolling was born on August 17, 1738, at Varina in Henrico County, the son of John Bolling and Elizabeth Blair Bolling and a great-great-grandson of Pocahontas and John Rolfe. In 1751 his father sent him to the Free Grammar School of Queen Elizabeth in Wakefield, England, which a number of other Virginia boys attended. Bolling excelled in languages. On his way back to Virginia he stopped off in London and on December 31, 1755, was admitted to the Middle Temple for legal studies. Bolling returned to Virginia the next year, arriving at Yorktown on April 16, 1756. For a year and a half he studied law under Benjamin Waller in Williamsburg.

After his father died in 1757, Bolling lived at his father's Chesterfield County plantation, Cobbs, until the middle of 1760, when he built a house called Chellow, or Chellowe, at his plantation in the portion of southern Albemarle County that became Buckingham County in 1761. From January 12 until September 16, 1760, Bolling courted Anne Miller, a distant cousin. His courtship journal, "A Circumstantial Account," and the poems he wrote provide a unique view of courtship among the eighteenth-century Virginia gentry. The romance ended when Miller sailed to Scotland with her father; she later married Sir Peyton Skipwith.

On June 5, 1763, Bolling married Mary Burton, of Northampton County. She died on May 2, 1764, two days after the birth of their daughter. Almost fourteen months later, on May 31, 1765, Bolling posted a marriage bond in Amherst County and married Susanna Watson on that day or early in June. They had two sons and two daughters.

At the first election after Buckingham County was formed, the voters chose Bolling for the House of Burgesses. He attended the assembly of 1761–1765 regularly and was appointed to the prestigious Committee on Propositions and Grievances in 1762. Assuming that the important assembly business was concluded, he left to be married before the last session adjourned, thereby missing the famous meeting of the House of Burgesses on May 29, 1765, when Patrick Henry presented the Virginia Resolves against the Stamp Act. Bolling either did not stand for reelection in the summer of 1765 or was defeated.

Bolling became embroiled in several controversies. He heard George Whitefield preach at Bristol Parish in Blandford in April 1765 and satirized his revivalistic preaching. Later, in Alexander Purdie and John Dixon's Williamsburg Virginia Gazette for June 20, 1766, Bolling precipitated a major crisis by questioning whether three members of the General Court had shown partiality in bailing their friend John Chiswell, who had been arrested and charged with murder. Writers hotly debated the question in the newspapers. William Byrd, one of the judges who allowed Chiswell bail, sued Bolling for libel. On October 16, 1766, Lieutenant Governor Francis Fauquier, presiding at a session of the General Court, instructed a grand jury to "punish the Licentiousness of the Press," but the jury refused to indict. Byrd subsequently challenged Bolling to a duel, but a few hours before the duel was to take place both men were arrested and jailed. After being bound over to keep the peace they were released.

Bolling was again involved in legal troubles in 1771. His youngest brother, Archibald Bolling, sued him, believing that he should have received the property that their brother Edward Bolling, who died in 1770, had left instead to Robert Bolling. Archibald Bolling's attorney, George Wythe, and Robert Bolling's attorney, Thomas Jefferson, prepared exhaustive statements of the case, both of which survive. Jefferson's argument remains one of the best examples of his abilities as a lawyer.

Bolling cultivated grapes, made wine on his estate in Buckingham County, and wrote a dissertation on wine making, a portion of which appeared in Purdie and Dixon's Williamsburg Virginia Gazette for February 25, 1773. The House of Burgesses awarded him £50 sterling a year for five years beginning in 1773 "in Order to enable him to prosecute his scheme of cultivating Grapes, for the making of Wine."

Literary Career and Later Years

Bolling is best known as a writer. He published more poetry than any other colonial American between 1759 and his death. His poems appeared in the Williamsburg newspapers on many occasions, such as on the arrival of Governor Botetourt in 1768, and were of several types, including a long elegy in John Dixon and William Hunter's Williamsburg Virginia Gazette of May 20, 1775, on the deaths of Virginia militiamen at the Battle of Point Pleasant the previous October during Dunmore's War (1773–1774). Bolling was probably the greatest student of Italian literature in colonial America, and he wrote poetry in Italian, French, and Latin as well as in English.

His verse ranged through the usual genres of eighteenth-century popular poetry but also included some extraordinary pieces, such as the amazingly grotesque poem "Neanthe" (ca. 1763), which reflected elements of Italian anti-Petrarchan traditions, colonial Virginia folklore, and English Hudibrastic poetry. In the earliest appreciation of Bolling's poetry, Pierre Étienne Du Ponceau extravagantly judged him "one of the greatest poetical geniuses that ever existed." Bolling also wrote a brief family history, which was translated from the original French and published in Richmond in 1868 as Memoir of a Portion of the Bolling Family in England and Virginia. It recorded his descent from the immigrant Robert Bolling and the granddaughter of Pocahontas.

In many other ways typical of the colonial Virginia gentry, Bolling served on the Buckingham County Court from its creation in 1761 until his death and by 1774 was the second-ranking member. Against his wishes he was appointed sheriff of Buckingham County in 1765, and he was a colonel of the Buckingham County militia by 1773. Bolling was elected to represent his county in the Virginia Convention of July–August 1775. He was present in Richmond on July 17, 1775, for the convention's opening. Four days later, on July 21, 1775, Robert Bolling died suddenly at Richmond, perhaps of a heart attack. "Poor Bob. Bolling has run his race," one of the delegates wrote, "adieu to Burgundy."