This article represents a pragmatic approach to humorous literature. Specifically, it focuses on the linguistic ways in which Woody Allen renders the broad theme of failure in his Mere Anarchy collection of short stories (2007), simultaneously engendering humour and providing amusement for his readers. The paper covers the following aspects: a summary of the thematic variations on failure in the short stories; a reflection about the character correlates around the central motif of the “loser” in the collection; a review of the concepts of linguistic humour and incongruity; and a textual analysis of the script oppositions underlying such stylistic devices as simile, understatement, and irony. The article thus aims to show that human failure and unhappiness can be successfully turned into humorous material and that Allen manages to blur the frontier between tragedy and comedy thanks to his linguistic expertise.