<jats:p>This article examines the relationship between C.G. Jung’s notion of the trickster and the Baudelairean concept of the flâneur in the context of three iconic heroes of popular culture – and in doing so explores the similarities between those three figures – Sherlock Holmes (from Conan Doyle’s original to Benedict Cumberbatch’s contemporary interpretation of the role) and the heroes of the television series House M.D. and Doctor Who. It suggests that by applying these models to these three characters – these eccentric and brilliant and apparently emotionally stunted outcasts – we may discover in these figures greater depths than had at first met the eye.</jats:p>