The studies treat the peculiarities of riddles functioning in different genres of literary discourse in three literary texts by the English writers L. Carroll’s «Alice’s Adventures in Wonderland, J. Tolkien’s «Hobbit, Back and Forth» and R. Austin Freeman’s «The Mysterious Visitor». The relevance of this work is determined by the interest of linguists to a riddle as a linguistic phenomenon, possessing a certain cognitive-pragmatic potential, and is still insufficiently researched. As a valuable source of knowledge about the culture and traditions of a particular ethnic group, the riddle has a great linguistic and cultural potential and reflects the variability of the world’s pictures. Coding an object of the existing reality in the riddle aims to create a problem situation for the guesser, who should demonstrate the flexibility and non-standard analytical or insight way of thinking. The purpose of the study is to describe the cognitive-pragmatic potential of riddles functioning in a literary tale and a detective story. It has been established that the riddle can be not only an independent communicative event, but also an integral part of complex literary genres. The use of riddles in literary discourse is motivated by the author’s intention and reflects the creative nature of thinking. In the fairy tale, the riddle is aimed at game communication with a reader, while in the detective discourse it represents the main genre-forming element around which the plot and the system of characters are built.