This chapter explores the genealogy of the phrase ‘from the sublime to the ridiculous’, tracing the saying from Romantic period attributions to Thomas Paine and Napoleon back to seventeenth-century debates about the sublime as a literary style. Ridiculousness haunts sublimity from Longinus’s discussions of the comic in his treatise to Kant’s consideration of humour as an affect uncannily akin to the sublime. Returning to Romantic period theorizations of the ridiculous, the chapter considers Jean Paul Richter’s aesthetics and his influence on S. T. Coleridge’s thinking about humour as providing alternative perspectives on key Romantic concepts including our relationship to nature, society, and childhood.