A Riddle Wrapped in a Mystery Inside An Enigma

"It's a mystery. Broken into a jigsaw puzzle. Wrapped in a conundrum. Hidden in a Chinese box. A riddle."

—The Riddler, The Long Halloween

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."

Not to be confused with Riddle for the Ages.

Examples of A Riddle Wrapped in a Mystery Inside An Enigma include:

Film

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.

Literature

Discworld:
- In The Fifth Elephant Lord Vetinari describes Uberwald as "a mystery inside a riddle wrapped in an enigma." Sergeant Colon misinterprets this and later refers to it as "a misery wrapped in an enema."
- 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".
From Tiassa, two guardsmen conversing, 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 The Wheel of Time (namely, in The Dragon Reborn): "Name hidden within name shrouded by name. Secret buried within secret cloaked by secret."

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."

Magazines

One white-paper front cover for Mad Magazine greatly exaggerated this trope for laughs.

Live-Action TV

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."
On Eureka, when the characters are trying to shut down an extremely powerful Death Ray Doomsday Device in the episode "Dr. Nobel," Henry calls the weapon "a riddle inside an enigma wrapped in ten inches of titanium alloy."
In the Supernatural episode "Free To Be You And Me," when Sam takes a Ten-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 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 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.
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 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 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.

Shawn on Psych once spoke of Juliet as being "an enigma wrapped in a little blonde riddle."
When Stephen Colbert uncovered "lost footage" from an interview with Bill O'Reilly on The Colbert Report, Stephen introduced it as "a conundrum wrapped in a riddle covered with a spicy enigma sauce."
A male-to-female transsexual Liz befriends on the first season of Nip Tuck is called "a conundrum wrapped in a 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.

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)

Music

The song '"For You" by Barenaked Ladies:

An enigma wrapped in a mystery
Or a fool consumed by fear

Tabletop Games

In Werewolf: The Apocalypse, both the Uktena (Magical Native Americans) and the Stargazers (ascetic Far Eastern monks) have been referred to as such.

Video Games

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!"
From Professor Layton and the Diabolical Box:

Wurtzer: How she [Granny Riddleton] does it is a conundrum wrapped in an enigma-stuffed mystery. Or, y'know, a mystenigdrum.

From 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.

Sturm's description in the Advance Wars games is "A riddle within a shadow, revealing nothing."

Web Comics

In Questionable Content, when someone references Raven's indecipherable status (Is she just a Ditz given to being unusually insightful, or a Genius Ditz who is Obfuscating Stupidity?), Raven responds, "I'm a mystery wrapped in an enigma wrapped in an AWESOME rack!"

Web Original

In one Weebl and 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."
In Wrestlecrap's induction for TNA's Last Rites Match from 2007, on the matter of 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".

Western Animation

The Simpsons episode "Lisa's Date With Density" sees Lisa describe Nelson as "a riddle wrapped in an enigma wrapped in a vest."
On The Penguins of Madagascar, Skipper calls Alice "a riddle, wrapped in mystery, and dunked in nasty sauce" in the cartoon short "All Choked Up."
Parodied in Histeria!. Winston Churchill 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 Monsters vs. Aliens, 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."
A play on the usual expression is used in the My Little Pony: Friendship Is Magic episode Maud Pie. Twilight and friends discuss their difficulty making friends with Maud, who is obsessed with (and apparently as boring as) rocks.

Rainbow Dash: "That pony is a riddle wrapped in a mystery inside an igneous."
Rarity: "Don't you mean 'inside an enigma'?"
Rainbow Dash: "No. I mean 'igneous'. It's a kind of rock. Ask me how I know that."