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The [[Trope Namer|trope name]] originates from a statement made by [[Winston Churchill|Sir Winston Churchill]] in 1939 about what role Russia might play in [[World War II]]:
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Not to be confused with [[Riddle for the Ages]].
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** In ''[[Discworld/Men At Arms|Men At Arms]]'', 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 ''[[Dragaera|Tiassa]]'', two guardsmen conversing, [[Literary Agent Hypothesis|as rendered by]] Paarfi of Roundwood:
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"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."
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== [[Live Action TV]] ==
* In one episode of ''[[Seinfeld]]'', Elaine and Jerry get into a discussion about the nature of Newman.
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'''Jerry:''' He's a mystery wrapped in a ''Twinkie.'' }}
* The ''[[Star Trek: Voyager]]'' episode "Riddles" sees The Doctor refer to the Vulcan brain as "a puzzle wrapped inside an enigma housed inside a cranium."
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* On ''[[News Radio]]'', Jimmy James once referred to himself, saying "I am a cipher--a cipher, wrapped in an enigma, and smothered in secret sauce."
* In [[The Pilot]] for the ''[[Witchblade (TV series)|Witchblade]]'' television series, after the titular artifact gauntlet bonds with Sara, she has the following exchange with Kenneth about what the artifact is.
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'''Kenneth:''' A mystery, wrapped in a riddle, and cloaked in a conundrum.
'''Sara:''' That doesn't help very much. }}
* Shawn on ''[[Psych]]'' once spoke of Juliet as being "an enigma wrapped in a little blonde riddle."
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* On ''[[Human Target]]'', Chance once told Winston, "You're like a... mystery wrapped in a riddle wrapped in... cashmere."
* On the penultimate episode of ''[[Burn Notice]]'s'' second season, Victor accuses Michael of this:
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'''Michael:''' I needed help selling a cover ID; nothing personal. }}
* On ''[[Will and Grace]]'', 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." in an early episode (with regards to a protein shake's side effects)
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== [[Music]] ==
* The song '"For You" by [[Barenaked Ladies]]:
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Or a fool consumed by fear }}
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* One of the title screen quips that appears after starting up the indie game ''[[Minecraft]]'' is, "A riddle wrapped in a mystery!"
* From ''[[Professor Layton and the Diabolical Box]]'':
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* From ''[[Mother 3]]'', during Chapter 2:
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* [[Big Bad|Sturm's]] description in the ''[[Nintendo Wars|Advance Wars]]'' games is "A riddle within a shadow, revealing nothing."
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