This chapter identifies a subgenre of the essay form – the dream-essay – and charts its trajectory from early modern philosophy, through the Romantic interest in vision and reverie. Arguing that that the dream-essay both arises from and extends the sceptical ethos of Cartesian philosophy, it discusses Montaigne’s position on dreams, René Descartes’s vocational dream, and Jean-Jacques Rousseau’s dream reveries. With this background established, it turns to the Romantic dreamers Samuel Taylor Coleridge, Charles Lamb, Leigh Hunt, and Thomas De Quincey, emphasising how, for these writers, dreaming – and writing about dreaming – elaborates a paradoxical form of consciousness which is also a form of expression. The chapter concludes with brief discussions of the contemporary writers Adam Phillips and W.G. Sebald.