The sixteen words in the U.S. Constitution’s Eighth Amendment have their roots in England’s Glorious Revolution of 1688–89. This Article traces the historical events that initially gave rise to the prohibitions against excessive bail, excessive fines, and cruel and unusual punishments. Those three proscriptions can be found in the English Declaration of Rights and in its statutory counterpart, the English Bill of Rights. In particular, the Article describes the legal cases and draconian punishments during the Stuart dynasty that led English and Scottish parliamentarians to insist on protections against cruelty and excessive governmental actions. In describing the grotesque punishments of Titus Oates and others during the reign of King James II, the Article sheds light on the origins of the language of Section 10 of the English Bill of Rights. That language became a model for similarly worded provisions in early American constitutions and declarations of rights, including the Virginia Declaration of Rights, that were linguistic forerunners of the Eighth Amendment. The U.S. Constitution’s Eighth Amendment, ratified in 1791, became the law of the land more than 100 years after the Glorious Revolution, though that provision of the U.S. Bill of Rights was shaped by the Enlightenment as well as by early American understandings of English law and custom. The Article describes the seventeenth-century origins of the Eighth Amendment’s prohibitions and the Enlightenment’s impact on eighteenth-century thinkers, while highlighting how existing American prohibitions against excessive bail, excessive fines, and cruel and unusual punishments are now understood to bar acts inconsistent with “the evolving standards of decency that mark the progress of a maturing society.” The Article concludes by outlining the implications of the Eighth Amendment’s history for modern American jurisprudence. In doing so, it provides a critique of the U.S. Supreme Court’s recent Eighth Amendment decision in Bucklew v. Precythe.