This article explores the distinctive artistic form of caricature and the philosophical treatment it receives in the work of Karl Rosenkranz (1805–1879), who gives it a central role in the context of his remarkable book The Aesthetics of Ugliness (Die Ästhetik des Hässlichen). Rosenkranz" legacy on this score is not much discussed (certainly in Anglo-American philosophical circles), but its importance for the development of post-eighteenth-century aesthetics—in particular, for an aesthetics that stretches beyond the conventional concerns with the beautiful and the sublime—can hardly be overstated. After a presentation of Rosenkranz" project on the aesthetics of ugliness, this article examines his take on caricature and its relation to philosophy (as well as philosophy's relation to caricature), and then takes up some pressing contemporary questions that arise for caricature's use of stereotypes.