A Stock Phrase 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 The Triple and dependent on the Rule of Three. Frequently, the last item of the phrase is changed to something completely different and irrelevant to mystery for Rule of Funny, 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 exaggeration.
The trope name originates from a statement made by Sir Winston Churchill in 1939 about what role Russia might play in World War II:
"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."
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."
In Oliver Stone's 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 Kennedy Assassination in a paranoia fueled rant.
In Holy Flying Circus, 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 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".
"Well," said Nill, "this is an enigma wrapped in, ah..."
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 The Wheel of Time (namely, in The Dragon Reborn): "Name hidden within name shrouded by name. Secret buried within secret cloaked by secret."
In one episode of 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 Star Trek: Voyager episode "Riddles" sees The Doctor refer to the Vulcan brain as "a puzzle wrapped inside an enigma housed inside a cranium."
In the Supernatural episode "Free To Be You And Me," when Sam takes a 10-Minute Retirement 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 Everybody Loves Raymond, 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 Eureka, when the characters are trying to shut down an extremely powerful Death RayDoomsday Device in the episode "Dr. Nobel," Henry calls the weapon "a riddle inside an enigma wrapped in ten inches of titanium alloy."
On Homicide: Life on the Street, 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 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 Nip Tuck is called "a conundrum wrapped in a riddle."
On One Tree Hill, 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 Psych once spoke of Juliet as being "an enigma wrapped in a little blonde riddle."
On NCIS, Tony once refers to Abby as, "A paradox wrapped in an oxymoron, smothered in contradictions and terms."
On Andromeda, Seamus calls Trance "an enigma wrapped in a riddle with a tail in the middle."
The X-Files 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 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:
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 The Pilot for the 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.
Valve's description of The Spy on the Team Fortress 2 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 Mario Kart: 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!"
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".
In one Weebl & Bob short, Bob describes the flat-packed pie they bought from Piekia as "a conundrum wrapped in an enigma wrapped in pastry, wrapped in a lie."
Bunchies, the memetic four-legged green llama-like creature, was described on its official website (now defunct) as "a riddle wrapped in a mystery wrapped in a glossy green skin."
In Homestuck, WV comments to himself that women are "a riddle draped in a mystery wrapped in post-apocalyptic shroudwear."