This paper considers substantive and methodological issues that are raised by the deployment of Goethe's notion of the Urphänomen in the work of Georg Simmel and Walter Benjamin. The paper is exploratory. I employ Goethe's idea, and his approach to empirical observation and theory more generally, to examine affinities and contrasts between the methodology of Simmel and Benjamin. Like Goethe, both Simmel and Benjamin make imaginative use of analogical reasoning, and their approaches resist conventional sociological classification as particular kinds of `theory'. Simmel and Benjamin are thinkers who seek to present their arguments in a mode which cannot be divorced from their substance. By comparing their approaches in relation to Goethe's idea, we can illuminate new aspects of Benjamin's historiography and Simmel's approach to societal and historical form.