Born in Boston, Massachusetts in 1757 to Royall Tyler and Mary (Steele) Tyler, Tyler attended the Boston Latin School, Yale and then Harvard, where he earned a reputation as a quick-witted joker. After graduation, he briefly served in the Massachusetts militia under John Hancock during the abortive Rhode Island expedition. In late 1778, he returned to Harvard to study law, and was admitted to the Massachusetts bar in 1780. He opened a practice in Braintree, Massachusetts, eight miles outside of Boston. After a brief stint in suppressing the 1787 Shays's Rebellion, Tyler moved to Boston and boarded in the house of Elizabeth Palmer. After unsuccessfully courting Abigail Adams for many years, in 1794, he wed the Palmers's daughter, Mary Palmer, took her to his new home in Vermont, and with her had eleven children. In 1801, Tyler was appointed to the Supreme Court of Vermont as an assistant judge, and was later elected chief justice. In 1812 he ran unsuccessfully for the US Senate. In 1826, he died in Vermont, of facial cancer that he had suffered from for ten years.