History Main / RiddleMeThis

* ''Webcomic/SluggyFreelance'': Played with during the Stormbreaker Saga with the [[http://www.sluggy.com/comics/archives/daily/19990808 Gatekeeper]] of [[http://www.sluggy.com/comics/archives/daily/19990811 Yffi.]]
* [[Webcomic/TheNonAdventuresOfWonderella Wonderella]] knows how to [[http://nonadventures.com/2009/08/15/a-sphinx-says-what deal with this.]]
* ''Webcomic/PepsiaPhobia'': Inconsequentia's sphinx Trivia is trying to come up with a new riddle. The old one (viz. the classic RiddleOfTheSphinx) was so obvious that even Phobia saw it coming (she was just letting Trivia finish to be polite, which Gastro has yet to learn).

* Subverted in ''Webcomic/{{Subnormality}}''. The sphinx meets Oedipus' ''mother.''[[note]] After melting Oedipus into dust when he guessed man - the correct answer was WOMAN[[/note]] When she learns [[ChildSupplantsParent who she's talking to]], the sphinx has a massive flipout about which one of them is considered the monster, and makes Oedipus' mother take her place.

* In ''Webcomic/{{xkcd}}'', the classic "KnightsAndKnaves" puzzle is sent up/parodied where there's three guards. One only tells the truth, one only lies, and one stabs people who ask tricky questions.
** Not to mention that in reality [[AltText the whole setup is just a trap to capture escaping logicians. None of the doors actually lead out.]]

* Played with in ''Webcomic/ArtificialTimeXS'' with Squish, the spellcaster whose spells are in the form of riddles. The problem is that if the target of the spell can correctly answer the riddle, the spell fails.

* This is the standard MO of ComicBook/TheRiddler, the {{Trope Namer|s}}, in the ''Franchise/{{Batman}}'' comics. DependingOnTheWriter, it could be a game he plays, or it could be an outright psychotic compulsion he feels he ''has'' to play.
-->''"Riddle me '''this'''... riddle me '''that'''... [[Film/BatmanForever who's afraid of the big, black Bat?]]"''
* Cluemaster, also from the Bat family comics, started out with a similar MO, leaving little clues at his crime scenes, until he was caught and sent to Arkham. The doctors there were actually able to ''cure'' him... of his compulsion to leave clues. It figures the one time the shrinks there can do their job, it makes a criminal ''tougher'' to catch.
* ComicBook/TheJoker - considering his many DependingOnTheWriter interpretations - also occasionally will leave "riddles", although they are more like jokes where Batman has to figure out the (usually lame) punch-line.
* In IDW's ''ComicBook/MyLittlePonyFriendshipIsMagic'', the final door in Queen Chrysalis' castle will only open if one of the characters answers a riddle.
-->'''Chrysalis:''' ...How is a Pegasus like a writing desk? Can you answer this riddle?\\
'''Pinkie:''' [[spoiler:[[MathematiciansAnswer Nope! I can't answer it!]]]]

* In Marvel's run of Hanna-Barbera's ''WesternAnimation/LaffALympics'' comic, the three teams are tasked with locating a ceramic purple pig to win back the charity money the gambler Lucky Starr won from the event treasurer. Starr bets a load on the Rottens to find it first and to hedge his bet he has minions make sure the Rottens find the clues first. The Rottens have the clues but are clueless as to solving it. Super Snooper of the Yogi Yahooeys figures it out: the trick is ''where'' the clues were found. (The purple pig was in Captain Caveman's club.)

** [[DirtyCoward Sir Robin]] wasn't so lucky. Same questions [[TheLastOfTheseIsNotLikeTheOthers until the third]].

* Cluemaster, also from the Bat family comics, started out with pretty much the same MO, leaving little clues at his crime scenes, until he was caught and sent to Arkham. The doctors there were actually able to ''cure'' him... of his compulsion to leave clues. It figures the one time the shrinks there can do their job, it makes a criminal ''tougher'' to catch.

** Yes, the answer is mistletoe and Loki is trolling the other god with his KryptoniteFactor. Poor Balder is also kind of clueless and refuses to answer so the next time we see him it's a DecapitationPresentation.

* Subverted in ''Webcomic/{{Subnormality}}''. The sphinx meets Oedipus' ''mother.''[[note]] After melting Oedipus into dust when he guessed man - the correct answer was WOMAN[[/note]] When she learns [[OedipusComplex who she's talking to]], the sphinx has a massive flipout about which one of them is considered the monster, and makes Oedipus' mother take her place.

* [[Webcomic/GastroPhobia Inconsequentia's]] sphinx Trivia is trying to come up with a new riddle. The old one (viz. the classic RiddleOfTheSphinx) was so obvious even Phobia saw it coming (she was just letting Trivia finish to be polite, which Gastro has yet to learn).

* WesternAnimation/ThePowerpuffGirls are tasked by the villain Him to solve a series of riddles in order to find their dad Professor Utonium in the episode "Him Diddle Riddle." Among them is to find out where it's boiling and freezing at the same time. The Mayor of Townsville susses it out--the global coordinates of 32 (freezing Fahrenheit) and 212 (boiling Fahrenheit) which leads to the Otto Time Diner. Or maybe an ice cream truck is on fire.

* On ''Anime/{{Pokemon}}'' (specifically, the aptly-named episode "Riddle Me This"), Blaine uses riddles to guide travelers to his holdings--an inn and his volcano-based gym.

* In Creator/LarryNiven and Steven Barnes' novel ''Literature/DreamPark'', one of the {{P|layerCharacter}}Cs must answer a series of riddles to save the party.

* ''Series/SoWeird'' had a variation that substituted trivia questions for riddles and instead of answering correctly to pass, the characters had to answer correctly to survive. (An incorrect answer would result in the character being turned into an eggplant.) The [[MonsterOfTheWeek monsters of the week]] were very sneaky and would con people into playing without realizing it. (By asking a seemingly innocent question and then changing the person when they didn't know the answer, even though the person hadn't actually agreed to the game.) Fi ends up having to play the game in order to save her friends and family.

'''Pinkie:''' [[spoiler: [[MathematiciansAnswer Nope! I can't answer it!]]]]

--->'''Asterix:''' [[spoiler: The beggar is a woman.]]

-->'''Obelix:''' [[spoiler: My father.]]

* On ''Series/{{Scorpion}}'', early in season 3 when Toby is trying to find out who Happy's mystery husband is, he pays Mark Collins a visit in prison. Collins doesn't say who it is, but gives him a riddle instead: "Water lies still, but water still lies. Add 50 and you'll have your answer." Toby solves it at the end of the episode. [[spoiler: The Roman numeral for 50 is L, when added to the middle of "water" gives the name "Walter".]]

* In the [[Literature/TheBible biblical]] story of Literature/SamsonAndDelilah, Samson challenges his wedding guests with a bet on the riddle, "Out of the eater came something to eat / Out of the strong came something sweet." The guests aren't able to guess it, so they resort to cheating by pressuring his wife to extract the answer from him. Samson [[BerserkButton doesn't take this well at all.]] (The answer is that [[spoiler: Samson killed a lion and discovered that bees had made honey in its carcass.]])

** The {{P|layerCharacter}}Cs must figure out which of five numbers (5, 7, 9, 11 and 13) didn't belong with the others [[spoiler: 9, which isn't a prime number]] or be attacked by flesh golems.

* Appears twice in ''VideoGame/DragonAgeOrigins'': a set of three in the Mage origin story, and a set of 10 as part of the gauntlet protecting the Sacred Ashes. The second set particularly fits the trope, because [[spoiler: the answer to each ghost's riddle is also symbolic of the part they played in the history of the Ashes. Piecing together the history beforehand helps you figure out the riddle, and the ghosts' spiel lets you better understand the quest itself and which of its outcomes is the good/bad one]].

* In ''VideoGame/PlanescapeTorment'' the witch Ravel presents travelers with the question "What can change the nature of a man?" Allegedly, she grants wishes to those who get the answer right, and if they got it wrong she killed them. Subverted harshly because [[spoiler: she's lying. She kills everyone whatever they answer, as she only cared about the Player Character's answer.]]
** The answer he originally gave was [[spoiler: "regret", but he later says that the answer really depended on who was being asked, and that there were many possible answers that were legit.]]
*** And then at the end you find out the true answer [[spoiler: Belief, for whatever you believe can change your nature is capable of changing you]]

** The solution (which has to be typed in, in contrast to the rest of the icon-based interface) is [[spoiler: Love; each line in the poem hints at one of the letters in the word successively.]]

* Spoofed in ''VideoGame/DragonAgeOrigins'' with the crazy old man in the forest who will only answer a question if you answer one of his questions first. But he doesn't have any good question at hand right now, so he just goes for "What... is yer name?".

* [[Webcomic/TheNonAdventuresOfWonderella Wonderella]] knows how to [[http://nonadventures.com/2009/08/15/a-sphinx-says-what/ deal with this]].

** In "Time Sandwich", Magic Man steals Jake's "ultimate sandwich" and traps it in a magical bubble where time moves slower on the inside. He tells Jake that the only way to break through is to solve his riddle: "When your face shows 7:20, when green leaves turn brown, the only way forward is down! Then you'll see, the wetter, the better." It turns out [[spoiler: when Jake [[DespairEventHorizon gets sad enough]], he's able to move through the time bubble at normal speed... [[HoistByHisOwnPetard unfortunately for Magic Man]].]]

When OnlySmartPeopleMayPass, a challenge is often given in the form of a riddle. The solution to said riddle is often, in itself, the means by which the characters may continue. (Unless the characters are GenreSavvy, in which case it may turn into OnlyTheKnowledgableMayPass.)

{{Sub Trope}}s include RiddlingSphinx (the tendency of sphinxes to do this), RiddleOfTheSphinx (a particular riddle that's very popular), TheseQuestionsThree (combining this trope with the RuleOfThree). See also the sister trope LifeOrDeathQuestion, which is when the same trope is simply a question (or multiple questions), and not a riddle.

* In ''[[Manga/TongariBooshiNoAtorie Witch Hat Atelier]]'', the golden people of the ancient city of Romonneau offer to let Tetia, Qifrey, and Coco pass if the students could answer a riddle. [[spoiler:The answer is "Peace". Magic took away the peace they had, leaving them with bodies that were always cold and uncomfortable.]]

{{Sub Trope}}s include RiddlingSphinx (the tendency of sphinxes to do this), RiddleOfTheSphinx (a particular riddle that's very popular), TheseQuestionsThree (combining this trope with the RuleOfThree).