By examining twenty-first-century negative political advertisements alongside Shakespearean fools and Erasmian folly, we can read attack ads not as barren clichés but as parables about the slippages—between subject and object, villain and hero, insider and outsider—that make possible more-generous appraisals of folly and that offer glimpses of a humanist program based on folly's benevolence. When we read such ads as Erasmian gestures—more than that, when we recognize our entanglements in the foolish maneuverings of our political leaders—we confront the possibility that giving in to the incongruities of folly is more productive than insisting on a knowing, superior sufficiency. To recognize the incapacitating, unconventional properties of folly is to affirm what is alluring, even precious, about rhetorical philosophies that favor not orderly, intelligible communities but profoundly, dramatically—laughably—indistinct ones.