Riddle-game was an ancient game of the Hobbits, used as a means of settling disputes. The players continued to ask each other riddles until one failed to provide a correct answer.
The origins of the game are not known, save that it was very ancient and its rules were agreed by the Authorities and respected as sacred.[note 1] According to Frodo, riddles of similar folk were asked by other folk besides hobbits, although Bilbo and Gollum knew the same ones.
The most famous riddle-game was the one in which Bilbo Baggins and Gollum competed. If Gollum failed to answer a riddle, he would show Bilbo out of the Misty Mountains. However, if Bilbo lost, Gollum would eat him. The two exchanged several riddles, and Gollum's knowledge of the answers suggested to Gandalf years later that he had possibly been a hobbit once. At last, strapped for riddles to ask the loathsome creature, Bilbo, touching the ring he had found in the tunnels, asked "What have I got in my pocket?".
Gollum assumed it to be a riddle, and while he had the right to reject it, his attempt to answer bound him to the rules of the game. Knowing it was an improper question, he was given three guesses, but he guessed incorrectly nonetheless. Reneging on his promise, Gollum plotted to use his "Precious" to murder and eat Bilbo, but when he found it missing, he too late guessed the right answer to Bilbo's "riddle".
In a letter, Tolkien made the following comment concerning the riddles appearing in The Hobbit: "There is work to be done here on the sources and analogues". Douglas A. Anderson has claimed to having identified possible inspirations behind eight out of nine riddles; José Manuel Ferrández Bru has noted a resemblance between the remaining riddle ("Voiceless it cries") with a riddle published by Cecilia Böhl de Faber. While admitting that the similarity between the two riddles is "surely a mere coincidence", Ferrández Bru also speculates that Tolkien may possibly have read or heard the poem in his youth through Father Francis Xavier Morgan, Böhl de Faber's great-niece.
- J.R.R. Tolkien, The Lord of the Rings, The Fellowship of the Ring, "The Shadow of the Past"
- J.R.R. Tolkien, The Hobbit, "Riddles in the Dark"
- J.R.R. Tolkien, The Lord of the Rings, The Two Towers, "The Road to Isengard"
- J.R.R. Tolkien, The Lord of the Rings, The Two Towers, "The Passage of the Marshes"
- Verlyn Flieger, "Poems by Tolkien: The Lord of the Rings", in Michael D.C. Drout (ed), J.R.R. Tolkien Encyclopedia: Scholarship and Critical Assessment
- J.R.R. Tolkien; Humphrey Carpenter, Christopher Tolkien (eds.), The Letters of J.R.R. Tolkien, Letter 25, (dated February 1938), p. 32
- J.R.R. Tolkien; Douglas A. Anderson, (ed.), (2002) The Annotated Hobbit: Revised and Expanded Edition
- José Manuel Ferrández Bru, "'Wingless fluttering': Some Personal Connections in Tolkien's Formative Years", in ’Tolkien Studies, Vol. VIII (eds. Douglas A. Anderson, Michael D.C. Drout, Verlyn Flieger), p. 54