After graduating from Harvard in 1776, Tyler briefly served in the Massachusetts militia during the American Revolution, including taking part in John Hancock's Rhode Island expedition.

Tyler had developed a reputation as a profligate while in college, supposedly squandering half his inheritance on parties, in grog shops and pursuing women after the death of his father.

In a letter to her husband John Adams, Abigail noted that despite having "a sprightly fancy, a warm imagination and an agreeable person," Tyler was "rather negligent in pursueing (sic) his business ... and dissipated two or 3 more years of his Life and too much of his fortune to reflect upon with pleasure; all of which he now laments but cannot recall."

John Quincy Adams apparently enjoyed Tyler's company, but questioned his integrity and did not think him suitable marriage material.

Tyler served again in the militia in 1787, as aide de camp to Benjamin Lincoln during the suppressing of Shays's Rebellion.

In 1796 Tyler married their daughter Mary, who was eighteen years younger, and they moved to Guilford, Vermont.

In 1812 he ran unsuccessfully for the United States Senate as a Democratic-Republican, losing the legislative election because by then the Federalists controlled Vermont General Assembly.

[4][5] He published The Algerine Captive in 1797 and wrote several legal tracts, six plays, a musical drama, two long poems, many essays, and a semifictional travel narrative, 1809's The Yankey in London.

In later life Royall Tyler admitted to his youthful arrogance and profligate conduct, but said he regretted only the limitations which his past placed upon his career and later ambitions.

He was believed to have fathered a child with Katharine Morse, the cleaning woman in the Harvard College buildings when Tyler was a student.

[citation needed] Tyler died in Brattleboro, Vermont, on August 26, 1826, as the result of facial cancer that he had suffered from for ten years.

[10] The Palmer family preserved stories of Tyler's sexual misbehavior as a young man, some of which were known to Hawthorne, and which he used in his novel.