A riddle is a puzzle, consisting of text with a question to answer.

Riddles have a distinguished literary ancestry, although the contemporary sort of conundrum that passes under the name of "riddle" may not make this obvious. Riddles occur extensively in Old English poetry, and also in the Old Norse literature of the Elder Edda and the skalds. The Exeter Book, a manuscript in Old English, preserves almost sixty versified riddles from the Old English literature. An example:

Mo­­e word frŠt. Me ■Št ■uhte
wrŠtlicu wyrd, ■a ic ■Št wundor gefrŠgn,
■Št se wyrm forswealg wera gied sumes,
■eof in ■ystro, ■rymfŠstne cwide
ond ■Šs strangan sta■ol. StŠlgiest ne wŠs
wihte ■y gleawra, ■e he ■am wordum swealg.
A moth ate words. I thought that was quite curious, that a mere worm, a thief in the dark, ate what a man wrote, his brilliant language and its strong foundation. The thief got no wiser for all that he fattened himself on words.

The answer called for by the poem is bookworm. The general technique is to obliquely refer to the subject by kenning and other sorts of figurative language; since kennings formed such an important element of alliterative verse forms in the Germanic languages, the riddles served the dual purpose of puzzling the poet's audience and teaching the lore needed to successfully use or understand the poetic language. The god Odin was a master of riddle lore, and sparred with several of his foes using contests of riddles. In the Vafthruthnismal, Odin defeats his foe by posing a question only he could possibly know the answer to.

In the Hebrew Bible, the hero Samson proposes a riddle to the Philistines, which centered around Samson's discovery of honey in the carcass of a lion. (Judges 14) In Greek mythology, riddles were the province of the Sphinx, a female monster who challenged passersby with riddles; those who failed to guess them were devoured. She famously asked Oedipus, "What is the animal that goes about on four legs in the morning, on two legs at noon, and on three in the evening?" The correct answer given by Oedipus was "Man," who crawls as a baby, walks upright as an adult, and goes with the help of a walking stick when elderly.

In J. R. R. Tolkien's The Hobbit, Gollum challenges Bilbo Baggins to a riddle competition; Bilbo wins the competition by asking Gollum, "What have I got in my pocket?", which Gollum could not answer. The answer, of course, was the One Ring, which Gollum had lost and Bilbo had since found. (Of course, many have pointed out that this is more of a "question" than a "riddle"; in the forward to the Lord of the Rings Tolkien pointed at that the Rules of the competition stated that Gollum had indeed lost, as he attempted to answer it instead of pointing out that it wasn't much of a riddle. By accepting it, his loss was binding).

In the Batman comic books, one of the hero's best known enemies is The Riddler who is personally compelled to supply clues about his upcoming crimes to his enemies in the form of riddles and puzzles. Stereotypically, they are the kind of simple riddles as described below, but modern treatments generally prefer to have the character use more sophisticated puzzles.

Contemporary riddles typically use puns and double entendres for humorous effect, rather than to puzzle the butt of the joke, as in:

When is a door not a door?
When it's ajar.
What's black and white and red all over?
A newspaper.
What's brown and sounds like a bell?
Why are all numbers afraid of number seven?
Because seven eight nine.

These riddles are now mostly children's humour and games rather than literary compositions.

A close relation the riddle is the trick question, which can be used to humiliate the answerer. They generally either have no good answer at all, or have a number of natural answers of which one or more can under closer scrutiny be ridiculed.

Some examples:

Are you a virgin, mister? (The particular answer does not matter, as long as it is boldly delivered.)
Boxers or Briefs? (Either answer is okay, but don't answer: "Depends.")
Have you stopped beating your wife?
If someone jumped on your back, would you beat him off?
If Jack was stuck on a horse, would you help Jack off the horse?
Does your mother know you're gay? (Supposes that the answerer does not want to admit homosexuality)

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