According to the chronicler Edward Hall, the execution of Sir Thomas More, who was sentenced to die on the gallows for refusing to acknowledge the Royal Supremacy, was characterized by a characteristically frivolous lack of decorum on the part of More himself, most notably on the scaffold itself. Both More’s evangelical opponents and his catholic allies noted his merry disposition. This article examines how the ideas of mirth and folly are woven through both More’s public career and the life of his close contemporary and nephew, the Catholic writer and playwright John Heywood. It considers the two men’s adoption and adaptation of classical and medieval notions of foolishness and comedy for their own ends in the dangerous years of Henry VIII’s Reformation. To understand More’s alleged lapse in judgment during his own execution and what this might suggest about the uses of mirth in pre-modern culture more generally, the article analyzes it in the context of his attitude towards theater and hisUtopiaas a satire for and of humanists.