In nineteenth-century comic writing, the umbrella represents a troublesome material world: umbrellas were always threatening to break, flip inside out or to disappear and reappear in the most mysterious fashion. The umbrella was a trope for oddness, resistance and perversity of intent. With the help of Alenka Zupančič’s theory of comedy, this article argues that the umbrella in the cultural imagination marks an unreliable world of signs. Umbrellas, with their troublesome peripatetic nature, become arbiters of human destiny. Comic writers, including Robert Louis Stevenson in ‘The Philosophy of Umbrellas’ (1871), claim that umbrellas are repositories of democratic personhood. But since umbrellas are supremely alienable, their owners remain mere placeholders of identity. Umbrella comedy plays with the idea that modern personhood is contained in a near-arbitrary and perverse system of signs.