->''"It's a mystery. Broken into a jigsaw puzzle. Wrapped in a conundrum. Hidden in a Chinese box. A '''riddle'''."''
--> --'''The Riddler''', ''ComicBook/TheLongHalloween''

A StockPhrase typically used to describe something that is immensely puzzling to figure out or extraordinarily complex to fully understand, often relying on hyperbole and, occasionally, sarcasm.

The phrase is often open to great interpretation and variation. Its three distinct-yet-related nouns allow for a plethora of setups and gags related to TheTriple and dependent on the RuleOfThree. Frequently, the last item of the phrase is changed to something completely different and irrelevant to mystery for RuleOfFunny, and the exact order of what's wrapped and inside what varies with almost every separate occasion the phrase is evoked. Sometimes, one of the three parts may be dropped for gags and line deliveries that require a faster pacing; conversely, additional clauses can be added for greater [[ExaggeratedTrope exaggeration]].

The [[TropeNamer trope name]] originates from a statement made by [[UsefulNotes/WinstonChurchill Sir Winston Churchill]] in 1939 about what role Russia might play in UsefulNotes/WorldWarII:

->''"I cannot forecast to you the action of Russia. It is a riddle wrapped in a mystery inside an enigma, but perhaps there is a key. That key is Russian national interest."''

Not to be confused with RiddleForTheAges.

----
!Examples

[[foldercontrol]]

[[folder:American Newspapers]]
* An article from January 2008 in ''The New York Times'' that explains why fortune cookies are absent from Chinese restaurants in China was titled "Solving a Riddle Wrapped in a Mystery Inside a Cookie."
[[/folder]]

[[folder:Fanfic]]
* At one point in the {{Homestuck}} fanfic ''Moirallegiance Is Science'', Vriska is described in this manner.
-->You're complicated. You're like a puzzle, wrapped in a mystery, sealed with obscurity, and shipped through the WTF postal service. [[MixedMetaphor That's just the package you come in]].''
[[/folder]]

[[folder:Films -- Animated]]
* In ''WesternAnimation/MonstersVsAliens'', General Monger refers to the top-secret prison Susan is taken to as "an X-File, wrapped in a cover-up, and deep-fried in paranoid conspiracy."
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[[folder:Films -- Live-Action]]
* In Oliver Stone's film ''Film/{{JFK}}'', David Ferrie uses the exact phrasing from Churchill's original quote when trying to convince Jim Garrison to drop his investigation into the [[WhoShotJFK Kennedy Assassination]] in a paranoia fueled rant.
* In ''Film/HolyFlyingCircus'', the character Alan Dick uses the phrase "he's a riddle wrapped in a mystery inside a shit" to describe Malcolm Muggeridge's unpredictability.
[[/folder]]

[[folder:Literature]]
* ''Literature/{{Discworld}}'':
** In ''Discworld/TheFifthElephant'' Lord Vetinari describes Uberwald as "a mystery inside a riddle wrapped in an enigma." Sergeant Colon misinterprets this and later refers to it as "[[{{Malaproper}} a misery wrapped in an enema]]."
** In ''Discworld/MenAtArms'', the clowns ask Colon to search for their late compatriot's real nose, despite the fact he had one. Vimes, reading the report, reflects that "the whole nose business looked like a conundrum wrapped up in an enigma, or at least in Sergeant Colon's handwriting, which was pretty much the same thing".
* From ''[[Literature/{{Dragaera}} Tiassa]]'', two guardsmen conversing, [[LiteraryAgentHypothesis as rendered by]] Paarfi of Roundwood:
-->"An Easterner with an Imperial Title!"
-->"Well," said Nill, "this is an enigma wrapped in, ah..."
-->"Another enigma?"
-->"Precisely."
* In ''Heat Rises'', Jameson Rook claims "What can I say? I'm an enigma inside a conundrum inside a condom."
* Used by Verin Sedai in ''Literature/TheWheelOfTime'' (namely, in ''The Dragon Reborn''): "Name hidden within name shrouded by name. Secret buried within secret cloaked by secret."
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[[folder:Live-Action TV]]
* In one episode of ''Series/{{Seinfeld}}'', Elaine and Jerry get into a discussion about the nature of Newman.
-->'''Elaine:''' Maybe he's an enigma--a mystery wrapped in a riddle.
-->'''Jerry:''' He's a mystery wrapped in a ''Twinkie.''
* The ''Series/StarTrekVoyager'' episode "Riddles" sees The Doctor refer to the Vulcan brain as "a puzzle wrapped inside an enigma housed inside a cranium."
* In the ''Series/{{Supernatural}}'' episode "Free To Be You And Me," when Sam takes a TenMinuteRetirement and tries to live a "normal" life, a girl curious to learn about Sam's past but at a loss of words to describe his peculiarity gives Sam the opportunity to quip that he's "a riddle wrapped inside an enigma wrapped inside a taco."
* On ''Series/EverybodyLovesRaymond'', Robert once described himself as "an enigma wrapped in a mystery." Ray promptly replied that Robert was more of "an idiot wrapped in a moron."
* On ''Series/{{Eureka}}'', when the characters are trying to shut down an extremely powerful DeathRay DoomsdayDevice in the episode "Dr. Nobel," Henry calls the weapon "a riddle inside an enigma wrapped in ten inches of titanium alloy."
* On ''Series/HomicideLifeOnTheStreet'', when Munch and Kellerman work on a case involving a suicide jumper killed by a stray shotgun blast on the way down from a tall building, Munch describes it as "a riddle, surrounded by a mystery, wrapped inside an enigma, and stuffed inside a body bag."
* On ''Series/NewsRadio'', Jimmy James once referred to himself, saying:
-->"I am a cipher--a cipher, wrapped in an enigma, and smothered in secret sauce."
* A male-to-female transsexual Liz befriends on the first season of ''Series/NipTuck'' is called "a conundrum wrapped in a riddle."
* On ''OneTreeHill'', Lucas once observes that despite Peyton's desire to express herself through her art, she doesn't want anyone to know it's her. Peyton responds to this, "I'm just a riddle wrapped in a mystery inside a bitch," but Lucas sees something else: A troubled artist.
* Shawn on ''Series/{{Psych}}'' once spoke of Juliet as being "an enigma wrapped in a little blonde riddle."
* In an early episode of ''Series/WillAndGrace'', Grace say to Will:
-->"You know, I thought I knew everything about you. But you're a mystery. Wrapped in a riddle. Surrounded by enigma. Growing boobies."
* When Creator/StephenColbert uncovered [[http://www.colbertnation.com/the-colbert-report-videos/166955/april-23-2008/the-lost-o-reilly-tapes-pt--1 "lost footage"]] from an interview with BillOReilly on ''Series/TheColbertReport'', Stephen introduced it as "a conundrum wrapped in a riddle covered with a spicy enigma sauce."
* On ''Series/{{NCIS}}'', Tony once refers to Abby as, "A paradox wrapped in an oxymoron, smothered in contradictions and terms."
* On ''Series/{{Andromeda}}'', Seamus calls [[HumanAlien Trance]] "an enigma wrapped in a riddle with a tail in the middle."
* ''Series/TheXFiles'' episode "Patient X" contains a variant on the trope phrasing. Agent Mulder, who has grown skeptical of the existence of extra terrestrials but, instead, believing the alien conspiracy to be a lie purported by the military to hide ''a different'' and all more sinister scheme, describes his belief in "a conspiracy wrapped in a plot inside a government agenda."
* On ''HumanTarget'', Chance once told Winston, "You're like a... mystery wrapped in a riddle wrapped in... cashmere."
* On the penultimate episode of ''BurnNotice's'' second season, Victor accuses Michael of this:
--> '''Victor:''' Boy, you are an enigma wrapped in a schizophrenic, Michael. First you ''don't'' shoot at me, then you arrange a little firing squad.\\
'''Michael:''' I needed help selling a cover ID; nothing personal.
* In ThePilot for the ''Series/{{Witchblade}}'' television series, after the titular artifact gauntlet bonds with Sara, she has the following exchange with Kenneth about what the artifact is.
-->'''Sara:''' What is this thing? What is the Witchblade?
-->'''Kenneth:''' A mystery, wrapped in a riddle, and cloaked in a conundrum.
-->'''Sara:''' That doesn't help very much.
* Mozzie in ''WhiteCollar'' sometimes describes himself as this.
* On the ''Series/DoctorWho'' episode ''[[Recap/DoctorWhoS33E12NightmareInSilver A Nightmare in Silver]]'', the Doctor refers to Clara as "a mystery wrapped in an enigma squeezed into a skirt [[DistractedByTheSexy that's just a little bit too... tight.]]"
* In ''Series/{{Elementary}}'', Sherlock Holmes' description of [[spoiler: Moriarty]] from the episode "The Diabolical Kind".
--> '''Sherlock:''' The woman is a riddle wrapped in a mystery inside an enigma I've had sex with. I would be lying if I said I was the strongest assessor of her motives at this point.
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[[folder:Magazines]]
* One white-paper front cover for ''Magazine/{{MAD}}'' greatly [[ExaggeratedTrope exaggerated]] this trope [[PlayedForLaughs for laughs]].
[[/folder]]

[[folder:Music]]
* The song '"For You" by Music/BarenakedLadies:
-->''"An enigma wrapped in a mystery"''
-->''"Or a fool consumed by fear"''
[[/folder]]

[[folder:Tabletop Games]]
* In ''TabletopGame/WerewolfTheApocalypse'', both the Uktena ({{Magical Native American}}s) and the Stargazers (ascetic Far Eastern monks) have been referred to as such.
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[[folder:Videogames]]
* Creator/{{Valve|Software}}'s description of The Spy on the ''VideoGame/TeamFortress2'' website begins, "He is a puzzle, wrapped in an enigma, shrouded in riddles, lovingly sprinkled with intrigue, express mailed to Mystery, Alaska..."
* Wario's official profile in ''VideoGame/MarioKart: Double Dash!!'' states that he is "a puzzle, wrapped in an enigma, wrapped in yellow."
* One of the title screen quips that appears after starting up the indie game ''{{Minecraft}}'' is, "A riddle wrapped in a mystery!"
* From ''ProfessorLaytonAndTheDiabolicalBox'':
--> '''Wurtzer''': How she [Granny Riddleton] does it is a conundrum wrapped in an enigma-stuffed mystery. Or, y'know, a mystenigdrum.
* From ''VideoGame/{{Mother 3}}'', during Chapter 2:
--> '''Wess:''' The Hummingbird Egg is a ball of secrets inside secrets that are inside even more secrets... Or something like that, supposedly, apparently.
* [[BigBad Sturm's]] description in the ''[[NintendoWars Advance Wars]]'' games is "A riddle within a shadow, revealing nothing."
* In ''{{Spectrobes}}'', this is the description for Mossax.
* In [[VideoGame/RatchetAndClankFutureToolsOfDestruction Ratchet & Clank Future: Tools of Destruction]], Zephyr describes the Lombax Secret as "a cipher, wrapped in an enigma, smothered in super secret sauce!"
* The Dragonborn expansion for TheElderScrollsVSkyrim has Neloth sending you on a FetchQuest for a Black Book that he believes he has located:
-> Neloth: Now, it's only a rumor of a whisper of a conjecture...
[[/folder]]

[[folder:Webcomics]]
* In ''QuestionableContent'', when someone references Raven's indecipherable status (Is she just a [[TheDitz Ditz]] given to being unusually insightful, or a GeniusDitz who is ObfuscatingStupidity?), Raven responds, "I'm a mystery wrapped in an enigma [[BuxomIsBetter wrapped in an AWESOME rack!"]]
* In ''{{Narbonic}}'', when Helen explains to Artie that she hopes sparing Dave what she went through will make up for the terrible things she's done, before adding "And then I can destroy those fools at the Symposium and RULE THE WORLD!", Artie comments "You're just a mystery wrapped in an enigma wrapped in a peculiar sense of ethics, aren't you?"
** The Director's Cut commentary says that while there's a backstory explaining why Helen is the way she is, Mell is "a mystery wrapped in an enigma wrapped in a very short skirt".
[[/folder]]

[[folder:Web Originals]]
* In one ''WeeblAndBob'' short, Bob describes the flat-packed pie they bought from [[FictionalCounterpart Piekia]] as "a conundrum wrapped in an enigma wrapped in pastry, wrapped in a lie."
* Bunchies, the [[MemeticMutation memetic]] four-legged green llama-like creature, was described on its [[http://www.wildpixels.com/bunchies official website]] (now defunct) as "a riddle wrapped in a mystery wrapped in a glossy green skin."
* In ''Webcomic/{{Homestuck}}'', WV comments to himself that women are "a riddle draped in a mystery wrapped in post-apocalyptic shroudwear."
* In Website/{{WrestleCrap}}'s induction for TNA's Last Rites Match from 2007, on the matter of [[http://www.wrestlecrap.com/induction%20files/lastrites/lastrites1.mp3 Sting describing death as a "choice" where one of those choices is, in fact, life]], RD calls the meaning and exact point of Sting's remarks a "riddle wrapped in an enigma wrapped in a crummy TNA storyline".
[[/folder]]

[[folder:Western Animation]]
* ''WesternAnimation/TheSimpsons'' episode "Lisa's Date With Density" sees Lisa describe Nelson as "a riddle wrapped in an enigma wrapped in a vest."
* On ''WesternAnimation/ThePenguinsOfMadagascar'', Skipper calls Alice "a riddle, wrapped in mystery, and dunked in nasty sauce" in the cartoon short "All Choked Up."
* Parodied in ''WesternAnimation/{{Histeria}}''. UsefulNotes/WinstonChurchill is shown saying the trope quote, and then we zoom out to reveal that he's behind the counter of a fast food restaurant.
* In ''WesternAnimation/TheTick'' he says something is "a riddle, wrapped in an enigma and smothered in secret sauce"
* In ''WesternAnimation/DuckDodgers'', The Eager Young Space Cadet describes the title character this way.
-->'''Cadet:''' He's so complicated, l-l-l-like a mystery wrapped in a r-r-r-riddle inside an enigma.
-->'''Manobrain:''' I'd say he's more like a halfwit wrapped in a hot dog bun inside a coloring book.
* In one ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' episode, Rainbow Dash [[ParodiedTrope parodies this phrase]] to describe Pinkie's sister Maud Pie, whose only outstanding characteristic seems to be her obsession with rocks.
--> '''Rainbow:''' That pony is a riddle wrapped in a mystery inside an igneous.
--> '''Rarity:''' Don't you mean 'inside an ''enigma'''?
--> '''Rainbow:''' No, I mean ''igneous''. It's a kind of rock. [[SarcasmMode Ask me how I know that]].
* In one episode of ''BromwellHigh'', during Mrs. Jackson explaining her separation from her husband to the main characters:
--> '''Mrs. Jackson:''' As Churchill said, Martin is "a riddle, wrapped in a mystery, wrapped in an enigma".
--> '''Keisha:''' [[BreadMilkEggsSquick Wrapped in a cocksucker.]]
--> '''Mrs. Jackson:''' [[DeadpanSnarker I don't think Churchill said that.]]
[[/folder]]

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