Philosophy takes place not only in the content but also in the form of great works of philosophy. In this experimental essay, this idea is applied to Civilization and its Discontents. Three competing hypotheses about the book’s literary form emerge as a result. The first one, taking its cues from Freud’s much-riffed-on title, looks at the book as a seedbed of theoretical riffs. The second hypothesis, arising from the inherent limitations of the first, presents the text cohering according to an array of conceptual oppositions. The third hypothesis likewise compels because of how it overcomes its predecessor. It is at issue when Freud worries that his discussion of guilt in Chapters 7–8 has ‘spoilt the structure’ of the text. Guilt is in the topic and the tone: it has snuck up on us. The concept of guilt that emerges from this series of readings of Civilization is then crystallized in the discussion of a curious passage from Book 24 of the Iliad.