Bouldin was born probably in Charlotte County, the son of Wood Bouldin and Joanna Tyler Bouldin. His father was a prominent local attorney, and his mother was a sister of Governor John Tyler, making him a cousin of President. Bouldin read law, possibly in his father’s office, and was admitted to the bar on December 6, 1802, by which time he was presumably about twenty-one years old. He married Ann Bickerton Lewis in Richmond on December 19, 1804. They had six sons and five daughters before she died on December 25, 1823. On March 7, 1825, Bouldin married Eliza Watkins Spencer, of Charlotte County. They had four sons.
With the patronage of such local leaders as the inimitable John Randolph of Roanoke, Bouldin won an enviable reputation among the state’s legal and political leaders, and on March 27, 1821, he received an interim appointment to the General Court to fill a vacancy caused by the resignation of Peter Randolph. On December 8, 1821, the General Assembly elected him to that seat on the court. He served through 1829, riding circuit to preside over criminal cases, hearing appeals from the county courts, and occasionally meeting at the semiannual sessions in Richmond with other members of the General Court to hear criminal appeals. The few opinions Bouldin wrote are generally characterized by a spare, concise style.
Bouldin’s law practice and plantation provided comfortably for his large family. At the time of his death he owned nearly 2,300 acres in three tracts in Charlotte County. His Golden Hills mansion was filled with fine furniture, a law library of more than 300 volumes, and nearly 100 volumes of literature. Thirty slaves worked the property, and he owned an elegant carriage and thirty horses.
Bouldin was a states’ rights advocate who ran in April 1829 for the House of Representatives at John Randolph’s suggestion and was elected to represent Buckingham, Charlotte, Cumberland, and Prince Edward counties. He was reelected two years later and served from December 7, 1829, to March 3, 1833. During his second term Bouldin sat on the Committee on Revolutionary Claims. He allied himself with other southern states’ rights. Bouldin’s one major congressional speech, delivered on May 31, 1832, was a stirring denunciation of protective tariffs as not only unconstitutional but also economically foolish and wicked. In preparation for the speech, he drafted a memorandum and detailed his stance in a letter to one of his sisters. After Bouldin delivered the address, he had it printed as a twenty-nine-page pamphlet.
In April 1833 Bouldin lost his bid for reelection to none other than his mentor Randolph, but on August 26, 1833, he was again elected to Congress to replace Randolph, who had died. Bouldin took his seat on December 2. On February 11, 1834, he rose to oppose President Andrew Jackson’s removal of federal deposits from the Second Bank of the United States. Before beginning, however, as he started to reply to a comment from a colleague, Bouldin suddenly collapsed and died. His wife rushed down from the gallery and had to be carried weeping from the chamber. Bouldin’s funeral service was held two days later in the House of Representatives, with the president, the cabinet, and the members of the Supreme Court in attendance. John Quincy Adams recorded the death and funeral in his diary and added that “Bouldin was a man of good disposition and sterling integrity, warped sometimes into great curvature by the political prejudices of the Virginia school.” His body was interred temporarily in the Congressional Cemetery in Washington, D.C., and then moved to the family cemetery at his Golden Hills estate near Drake’s Branch in Charlotte County.