History Main / ARiddleWrappedInAMysteryInsideAnEnigma

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

[[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]]

* ComicBook/TheRiddler himself is an example of this--his entire identity (Mr. E. Nygma) is a pun on the phrase.

[[folder:FanWorks]]

* In ''[[Fanfic/SkyholdAcademyYearbook I Must Be Going]]'', [[VideoGame/DragonAgeInquisition Dorian informs Solas]] that "You are an enigma wrapped in a mystery wrapped in no shoes."
* In ''Fanfic/RocketshipVoyager'', the crew are puzzling over a BigDumbObject that [[ArtificialGravity doesn't spin to produce gravity]], in orbit around a previously unencountered phenomenon known as a [[UsefulNotes/BlackHoles black star]]. Captain Janeway describes it as "a riddle of a space station, orbiting an enigma."
* ''[[https://archiveofourown.org/works/7258183 i'm not a riddle wrapped in a mystery, i'm you wrapped in blood]]'' is the title of an ''Series/{{Arrow}}'' [[IncestYayShipping Tommy/Thea]] fanfic by kwritten.

--> The last time Severus Snape had seen Harriet Potter, the stubborn girl had been an enigma wrapped in a mystery, covered again in a glaringly obvious white sheet.

* 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."

* In Oliver Stone's film ''Film/{{JFK}}'', David Ferrie refers to the [[WhoShotJFK Kennedy Assassination]] as "a mystery wrapped in a riddle inside an enigma" when trying to convince Jim Garrison to drop his investigation during 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.
* In ''Film/HalloweenResurrection'', Freddie (Busta Rhymes) hypes up the premise of his reality television show filmed inside the old Myers residence as "a mystery wrapped up inside of a riddle inside of an enigma."
* ''Film/KnivesOut'': {{Parodied}}. Benoit Blanc explains his view of the mystery with an overly convoluted metaphor:
->'''Benoit Blanc:''' I spoke in the car about the hole in the center of this donut. And, yes, what you and Harlan did that fateful night seems at first glance to fill that hole perfectly... A donut hole in the donut's hole. But we must look a little closer. And when we do, we see the donut hole has a hole in its center - it is not a donut hole at all but a smaller donut with its own hole. And our donut is not a hole at all!

** In ''Literature/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 ''[[Series/{{Castle}} Heat Rises]]'', Jameson Rook claims, "What can I say? I'm an enigma inside a conundrum inside a condom."

-->'''Elaine:''' Maybe he's an enigma--a mystery wrapped in a riddle.\\

* 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."
* ''Series/LostGirl''. Thus spake Kenzi: "It is a riddle, cloaked in a mystery, wrapped in layers of ''[[EatingTheEyeCandy hot, hot manliness!]]"''
* 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 transgender woman Liz befriends on the first season of ''Series/NipTuck'' is called "a conundrum wrapped in a riddle."
* On ''Series/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."

-->'''Grace''': *''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 Creator/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 in 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 extraterrestrials 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 ''Series/HumanTarget'', Chance once told Winston, "You're like a... mystery wrapped in a riddle wrapped in... cashmere."
* On the penultimate episode of ''Series/BurnNotice's'' second season, Victor calls Michael "an enigma wrapped in a schizophrenic." (Michael had taken advantage of Victor spying on him to help sell his cover ID to a mark, which involved gunfire.)
* 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.

* Mozzie in ''Series/WhiteCollar'' sometimes describes himself as this.
* ''Series/DoctorWho'':
** In "[[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 a writing competition where the contestants had to come up with a description of Creator/MattSmith's Doctor InTheStyleOf Creator/TerranceDicks, the winning entry was the following:
--->'''Ian Hewett:''' A slim mismatched jigsaw of a man, paintbrush hair atop a young face with ancient eyes, an enigma wrapped in a bow tie.
** And this runner-up:
--->'''sammorgan 11:''' He looked like an alien crammed into the body of a human who had been crammed into the clothes of a maths teacher.
* 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.
* In an episode of ''Series/ThirdRockFromTheSun'', Dick describes an imagined conspiracy as "a riddle wrapped around an enigma fried up in a conundrum with Chinese mustard dipping sauce".
* A segment of the "La Leyenda del Tio la Vara" series of sketches from ''Series/LaHoraDeJoseMota'' had Father Tornices saying the trope name word for word.
* ''Series/{{Lucifer}}'' describes Ella as "an enigma wrapped in a hoodie under a jaunty ponytail."
* In ''Series/OnceUponATime'', Emma describes newcomer August as "a typewriter wrapped in an enigma wrapped in stubble".
* On ''Series/DegrassiTheNextGeneration'', when hanging out with Imogen, Clare describes Eli with the trope name. Imogen comments that he sounds like a burrito.
* In an ''Series/{{MST3K}}'' episode, Jonah Heston calls 1961 film ''The Mask'' "a riddle wrapped in a mystery seen through a migraine-inducing idea of 3D glasses".

* One white-paper front cover for ''Magazine/{{MAD}}'' greatly [[ExaggeratedTrope exaggerated]] this trope [[PlayedForLaughs for laughs]].

* 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..."

%%* ''VideoGame/ProfessorLaytonAndTheDiabolicalBox'':%%Quotes aren't acceptable context.
%%--> '''Wurtzer''': How she [Granny Riddleton] does it is a conundrum wrapped in an enigma-stuffed mystery. Or, y'know, a mystenigdrum.

%%--> '''Wess:''' The Hummingbird Egg is a ball of secrets inside secrets that are inside even more secrets... Or something like that, supposedly, apparently.
* ''VideoGame/AdvanceWars'': [[BigBad Sturm's]] description is "A riddle within a shadow, revealing nothing."

* ''VideoGame/RatchetAndClankFutureToolsOfDestruction'': Zephyr describes the Lombax Secret as "a cipher, wrapped in an enigma, smothered in super secret sauce!"
* ''Franchise/TheElderScrolls''
** ''VideoGame/TheElderScrollsVSkyrim'': The ''Dragonborn'' expansion 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...
** ''VideoGame/TheElderScrollsOnline'': In the Mages Guild questline, [[MadGod Sheogorath]] describes the trials needed to get his books as "a contest, wrapped in a mystery, with an enigma glaze."
* ''VideoGame/{{Brawlhalla}}'': The description for the legend of Orion is "A riddle wrapped in an enigma wrapped in Ivaldic battle armor."

* In ''Webcomic/QuestionableContent'', when someone references Raven's indecipherable status (Is she just a [[TheDitz Ditz]] given to being unusually insightful, or a GeniusDitz with ObfuscatingStupidity?), Raven responds, "I'm a mystery wrapped in an enigma [[BigBreastPride wrapped in an AWESOME rack!"]]
* In ''Webcomic/{{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?"

* In ''Webcomic/{{Homestuck}}'', WV comments to himself that women are "a riddle draped in a mystery wrapped in post-apocalyptic shroudwear."

* In one ''WebAnimation/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 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."
* In one of his reviews of nostalgic commercials, WebVideo/TheNostalgiaCritic describes UsefulNotes/{{Canada}} as "like a riddle inside an enigma inside a please and thank you."

* ''WesternAnimation/TheSimpsons'' episode "[[Recap/TheSimpsonsS8E7LisasDateWithDensity 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."

* 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.

* In one episode of ''WesternAnimation/BromwellHigh'', as Mrs. Jackson is 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:''' Wrapped in a cocksucker.\\
'''Mrs. Jackson:''' I don't think Churchill said that.
* In the ''WesternAnimation/DragonsRidersOfBerk'' episode [[Recap/DragonsRidersOfBerkS4E9EdgeOfDisasterPart2 "Edge of Disaster Part 2"]], Tuffnut says about Heather, "One might say she's an enigma, wrapped in a riddle, wrapped in yak bacon."

* In an ''Series/{{MST3K}}'' episode, Jonah Heston calls 1969 film ''Film/TheMask'' "a riddle wrapped in a mystery seen through a migraine-inducing idea of 3D glasses".

* A male-to-female transsexual Liz befriends on the first season of ''Series/NipTuck'' is called "a conundrum wrapped in a riddle."

* In ''[[ComicBook/SpiderMan The Amazing Spider-Man]]'' #26, the narrator asks, "Can Spider-Man solve this dark riddle, cloaked within a grim puzzle, hidden beneath the shadows of a deadly enigma?"

* In ''[[Fanfic/SkyholdAcademyYearbook I Must Be Going]]'', [[VideoGame/DragonAgeInquisition Dorian informs Solas]] that "You are an enigma wrapped in a mystery wrapped in [[DoesNotLikeShoes no shoes]]."

* In ''TabletopGame/WerewolfTheApocalypse'', both the Uktena ({{Magical Native American}}s) and the Stargazers (ascetic Far Eastern monks) have been described as such.

* 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 ''VideoGame/{{Minecraft}}'' is, "A riddle wrapped in a mystery!"
* From ''VideoGame/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 ''[[VideoGame/NintendoWars Advance Wars]]'' games is "A riddle within a shadow, revealing nothing."
* In ''VideoGame/{{Spectrobes}}'', this is the description for Mossax.
* In ''VideoGame/RatchetAndClankFutureToolsOfDestruction'', Zephyr describes the Lombax Secret as "a cipher, wrapped in an enigma, smothered in super secret sauce!"

** The ''Dragonborn'' expansion for ''[[VideoGame/TheElderScrollsVSkyrim Skyrim]]'' has Neloth sending you on a FetchQuest for a Black Book that he believes he has located:

** In the Mages Guild questline in ''VideoGame/TheElderScrollsOnline'', [[MadGod Sheogorath]] describes the trials needed to get his books as "a contest, wrapped in a mystery, with an enigma glaze."
* In ''VideoGame/{{Brawlhalla}},'' the description for the legend of Orion is "A riddle wrapped in an enigma wrapped in Ivaldic battle armor."

* In ''Webcomic/QuestionableContent'', when someone references Raven's indecipherable status (Is she just a [[TheDitz Ditz]] given to being unusually insightful, or a GeniusDitz with ObfuscatingStupidity?), Raven responds, "I'm a mystery wrapped in an enigma [[BuxomIsBetter wrapped in an AWESOME rack!"]]

[[/folder]]

See {{Riddle}}. Not to be confused with RiddleForTheAges.

Not to be confused with RiddleForTheAges.

-->-- '''ComicBook/TheRiddler''', ''ComicBook/TheLongHalloween''

* On ''Series/{{NCIS}}'', Tony once refers to Abby as "A paradox wrapped in an oxymoron, smothered in contradictions and terms."

** And this Runner Up:

* In ''TabletopGame/WerewolfTheApocalypse'', both the Uktena ({{Magical Native American}}s) and the Stargazers (ascetic Far Eastern monks) have been referred to as such.

* In ''Webcomic/{{Homestuck}}'', WV comments to himself that women are "a riddle draped in a mystery wrapped in post-apocalyptic shroudwear."

[[/folder]]

----

[[folder:Videogames]]

--> '''Neloth:''' Now, it's only a rumor of a whisper of a conjecture...

--> '''Rainbow:''' That pony is a riddle wrapped in a mystery inside an igneous.\\

--> '''Mrs. Jackson:''' As Churchill said, Martin is "a riddle, wrapped in a mystery, wrapped in an enigma".\\

* ''VideoGame/TheElderScrolls''
** The Dragonborn expansion for ''VideoGame/TheElderScrollsVSkyrim'' has Neloth sending you on a FetchQuest for a Black Book that he believes he has located:

* The Dragonborn expansion for ''VideoGame/TheElderScrollsVSkyrim'' has Neloth sending you on a FetchQuest for a Black Book that he believes he has located: