Rigged Riddle

"Not fair! not fair! It isn't fair, my precious, is it, to ask us what it's got in it's nassty little pocketsess?"

- Gollum

Riddle Me This: What kind of game do you never get the chance to play, because you've always lost before you've begun?

Answer: A Rigged Riddle.

Specifically, where most riddles may have more than one applicable answer and is more a straightforward test of knowledge and/or creative thinking, the Rigged Riddle relies on very specific information that the answering party could not (or rather should not) possibly know.

The riddle itself need not be completely impossible - just heavily unbalanced against whoever's being asked. This almost always involves information that only the one asking is privy to, and may even be personal info of some sort on their part, though it need not always be the case - the important part is that whatever they know, the one answering ideally shouldn't.

If they're especially unscrupulous, the riddle-maker will lead the unsuspecting party in one direction with the riddle, only for the answer to be something completely different. (Not to Be Confused With the other Something Completely Different.)

As such, overcoming this riddle requires a seriously sharp deductive mind to figure out the right angle to approach, let alone solve it outright - in some cases, it may seem like the answer was manufactured out of thin air. It may also warrant a wit capable of achieving the goal regardless of what the answer may be. While this is more than "just" a difficult riddle that the riddle-maker is confident cannot be answered, it's still possible for them to thoroughly underestimate the cunning of their target.

Rigged Riddles are often the domain of very powerful (or very spiteful) Riddling Sphinxes and Trickster Gods. Variations on the Knights and Knaves logic puzzle are a common type of Rigged Riddle, usually involving the reveal that the "knight" and "knave" are actually both liars.

It's possible for a Rigged Riddle to be benign, though&mdash;it may even be a hint towards a stranger's identity, or a way to fish out a duplicitous bystander.

The Shell Game is a related trope that's often similarly rigged against the "player".

Anime and Manga

 * Yu-Gi-Oh! has the Paradox Brothers ("Meikyū Brothers" in the English manga) attempt this after losing their duel against Yugi and Joey. Both brothers claim that one of the exits will let them leave the caves, while the other simply leads to an endless maze, before using the Knights and Knaves routine and challenging them to answer. Yugi realizes that both brothers are actually lying, and have the ability to change which path leads where&mdash;he successfully tricks this knowledge out of them using a Two-Headed Coin, allowing him and his friends to move forward.

Comic Books

 * The Riddler, alias Edward Nygma, naturally tends towards this type of riddle when he really wants to humiliate someone. Unfortunately for him, he often sets his sights on Batman, who he is frequently Out-Gambitted and humiliated by. Bats ain't the World's Greatest Detective for nothin'.

Literature
""The cock crew, The sky was blue: The bells in heaven Were striking eleven. ‘Tis time for this poor soul To go to heaven."
 * In The Hobbit, Bilbo asked Gollum “What have I got in my pocket?” Understandably, Gollum asserts that this riddle isn't fair. Funny thing is, Bilbo was actually talking to himself when he said this, but Gollum interpreted it as part of their riddle game, and it is only after Gollum protested that Bilbo deliberately used it as the riddle.
 * Alice in Wonderland subverts this. At the Mad Tea Party, the Hatter himself asks this perplexing question of Alice: "Why is a raven like a writing desk?" Once Alice gives up and asks for the answer, the Hatter reveals he has no idea himself - he was asking a genuine question.
 * Lewis Carroll admitted that he'd not thought of an answer himself, but readers proceeded to pester him so much on the matter that he eventually wrote one in a preface to a later edition of Wonderland: "because it can produce a few notes, though they are very flat; and it is never put with the wrong end in front!"
 * Noted nineteenth-century puzzle expert Sam Loyd devised his own answer: "because Poe wrote on both".
 * Ulysses, the James Joyce Doorstopper, has Author Avatar Stephen Dedalus teaching a class on Roman history and pose a riddle to his students:


 * The answer? Many scholars conclude that this is Joyce's way of poking run at riddles and the people who take them too seriously; Don Gifford explicitly notes this in his article "The Cock Crew": An Answer to the Riddle as "unanswerable unless the answer is already known".

Oral Tradition, Folklore, Myths, Religion, and Legends

 * Odin did this a couple of times in Norse Mythology - once in Hervarar saga ok Heiðreks (The Saga of Hervör and Heidrek), where a disguised Odin asked numerous riddles of King Heidrek, and again in the poem Vafþrúðnismál with Vafþrúðnir, who exchanged riddles with Odin. On both occasions, he used the same question: "What did Odin speak into Baldr’s ear before he was placed on the pyre?"
 * In The Bible, Samson tore apart a young lion on the way to wed his first wife (a Philistine woman), and when he later came across the corpse, a beehive filled with honey was inside. Samson used that as the basis of the following riddle: “Out of the eater, something to eat; out of the strong, something sweet.” Samson offered a prize of 30 soft under shirts (sedin) and good suits (chalipha) to the winner.
 * This is one of the earliest examples of a Rigged Riddle that is "properly" formatted as a riddle, rather than a straightforward question with a secret answer - regardless, the Philistines present could not solve it, and instead turn to Samson's wife, who weasels the answer out of him. Samson realized this, but resolved to make good on his bet regardless - by traveling to Ashkelon and taking the clothes from the thirty Philistines he would murder there. This would culminate in a divorce and set in motion a divinely-ordained series of escalating fights between Samson and the Philistines.
 * What is Rumpelstiltskin’s name?

Video Games
"Dr. Young: Patient interview 21. Patient's name is Edward Nigma, also known as the Riddler. So, Edward. Warden Sharp tells me you've been leaving threatening riddles scrawled on the asylum walls, again. Riddler: One would have to be severely paranoid to read threats into harmless riddles, Doctor Young. May I test you with one? Dr. Young: Very well. Riddler: What is it that walks on four legs, then two legs, and finally three legs? Dr. Young: A human being. As a baby it crawls on four legs, as an adult it walks around on two and in later years it uses a cane. Riddler: (laughs) Good try, but the answer to all three is a baby. True, it crawls on all fours, but cut off its legs and it can only wiggle on two limbs. Give it a crutch, it can hobble around on three. You see? Dr. Young: That's horrible. How can you even joke about that? Riddler: Easily, Doctor. It’s not my baby."
 * The Riddler is especially guilty of this in the Arkham series of Batman games, considering he outright accuses Batman (and by proxy the player) of cheating multiple times as the Dark Knight overcomes his more difficult challenges and eventually defeats him.
 * The interview tapes from Batman: Arkham Asylum have another example that perfectly demonstrates Nygma's Smug Snake personality with his take on the famous Riddle of the Sphinx. This being Arkham, and Nygma being Nygma, his is... a little mean-spirited to say the least.