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Avatar: The Last Airbender

  • Bring Me All Your Elderly! has movie!Zhao, who is In possession of knowledge from the Super Secret Spirit Library!!!... erm, slightly more unhinged than usual.

Axis Powers Hetalia

  • Gankona, Unnachgiebig, Unità: To say Italy is hard to read is a massive understatement, even to his family and closest friends. His mind is just too strange after all. So strange, that nobody saw his internal misery beneath his brilliant smiles.
  • Part Right, Half Wrong, a Third Crazy
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    • Mattie, a beautiful combination of Cloudcuckoolander and Deadpan Snarker ("The lamp, by the way, is a terrible conversationalist"). Where would we be without his arguments with his bedside lamp, among other things?
    • Gilbert ("may or may not be wearing only a cape right now").

Calvin and Hobbes

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Crossovers

  • In The Bridge, Megalon is basically a Kaiju version of Pinkie Pie.
  • Child of the Storm has the usual example of Dumbledore (who happily exploits his reputation for political gain, magical advantage, and psychologically tormenting Cornelius Fudge), and Doctor Strange, who sometimes seems as if he lost his marbles a very long time ago, generally being quirky, sarcastic, strangely dressed and all-round odd. However, as is revealed, while he probably is mad, he's also by far the most switched on character in the cast, a Seer and Time Master without peer, and a schemer who's considered a member of the Omniscient Council of Vagueness for very good reason.
  • Dungeon Keeper Ami features Cerasse- one of the fairy sisters. She has a thing for Tserk, one of Ami's minions... A tentacle monster- to the extent that she has a great deal of trouble preparing calimari ("Oh, I can't! The poor little tentacles!"). When the sisters contemplate 'rescueing' Jadeite from Mercury, she is quick to volunteer that they ought to rescue Tserk as well, earning her some strange looks...
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  • In Hunting the Unicorn, Nick of the Warblers is a Hot-Blooded stoner who's prone to strange logic despite his general intelligence. He has "three definitions of truth" according to Wes, his Coming-Out Story at sixteen involved getting drunk and high after his mother kicked him out, and when his best friend Jeff is upset at being the last one to find out about his bisexuality, Nick offers to pretend it didn't happen yet. Jeff's response is "Nick, you can't redo coming out!"
  • Roanapur Connection: So far, OC Nathan Andre seems to be somewhat quirky in how he acts or speaks at points. Main example of when he came skipping into a meeting between Ganabati and the exiled Maharajah and Maharani. Or the fact he carries a snake around on his shoulders in public. Though there are hints that he likes to Obfuscating Stupidity around certain people.
    • Oboro Shinozaki/Kirihara is shown in a few of her internal thoughts in Father, Son and the Mother Hen to be quirky herself with the she way she narrates breaking her legs for a year once trying to fly with that it caused her to awe. Or the fact she has a picture of a duck in her guest room.
  • In Teenage Jinchuriki Shinobi, Michelangelo is the only one not disturbed by Jiraya and Gai's poses and behaviorisms, something of which the latter was enough to make Naruto warn his team to not look.
  • A Wild Badfic Appeared! Commentaries: Sudz/Dax the Greninja. Sure, he might look like a cool ninja frog creature, but mentally he's a very young child.
    Pit: This girl is completely coo-coo! *spins pointer finger around ear* She doesn't know what she's saying!
    Calem: Kind of like Sudz here.
    Sudz: That's moi!
    • Also, erikatheraindeer's interpretation of the female player character of Pokémon Sun and Moon, here named as "Selene", is even more of this than Sudz. Since the player can lie in the beds of many a NPC and comment on their emotional state (something which her cousin/companion/the male player character Elio references in the opener of their debut episode), among many, many other things that would make them come across as this in Sun and Moon, this isn't without precedent. Still, this kid debuts by sniffing an unfortunate Robin.
      (blushing, eyes sparkling, and cheerfully) "Hey handsome! You're really cute! And you smell good too!"
    • Ness has shown minor shades of this, such as apparently once thinking of using Kirby as a gun, or regularly making use of a literal notebook full of ever-changing Unusual Euphemisms and strange catchphrases. Considering he was written to reflect the series he is from, this is to be expected. In fact, considering this, he's much more grounded than he could have been.
    • Pit and Palutena have also shown varying shades of this with their playful senses of humor. Since they have already shown moments of this in canon, especially the former, it isn't too unexpected.

Harry Potter

  • In All the Dementors of Azkaban Harry is depicted as nearly as much of a Cloudcuckoolander as Luna, from trying to "make friends" with Dementors by offering them chocolate to painting Azkaban pink at Luna's request to cheerfully running errands in Diagon Alley for prisoners like the Lestranges.
  • In Session Transcripts brain damage from more-abusive-than-canon treatment by the Dursleys results in Harry being extremely Cloudcuckoolander-ish when he shows up at Hogwarts, spouting random remarks like "I can't eat a table, but I tried to eat my door once because I was so hungry. It didn't taste very good and I chipped a tooth." and "Plants talk to me sometimes, but sometimes they're allergic to me and I make them sneeze."
  • DRACO MALFOY in A Very Potter Musical.
    • Snape is an even bigger example, especially in the Potion Master's Corner.
    • And then there's Gilderoy who dreams of becoming king of the mice.

Homestuck

  • Ganmed Lomust in Hivefled. Spacey, Obliviously Evil subjugglator who writes truly terrible fanfiction. One of the more popular fantrolls, probably for this exact reason.

The Lion King

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My Little Pony: Friendship Is Magic

  • A Brief History of Equestria mentions that most contemporary portrayals (mainly Hearth's Warming Eve pageants) of Chancellor Puddinghead are severely downgraded from the original, whose behavior bordered on The Caligula mixed with Groucho Marx. In other words, when Pinkie Pie was ranting about 'thinking inside the chimney' and wearing a map on her face, she was trying very hard to be solemn and dignified.
  • The Changeling of the Guard: Exiled changeling protagonist Idol Hooves, having spent most of his life in the hive and being mostly ignorant as to how the outside world works, has some very strange ideas and thought processes, some of which threaten to expose him for what he truly is. He genuinely has no idea what things like jail cells and cement are, and takes a leisurely stroll through an ancient booby-trapped crypt without realizing that the traps are supposed to be deterring him.
  • Mirror Rarity in The Dark Side of the Mirror Verse. Her misunderstanding of social rules and fashion ideas in general is so mixed up, she genuinely thinks her bizarre fashion tastes are completely normal and following the rules, and that her vandalism is simply improving things. Justified, as her parents stuffed her head so full of contradictory ideas and rules, she ended up not entirely sane trying to apply all of them at once instead of applying different ones to different situations. She gets a bit better thanks to Mirror Flim and Flam, but still remains a bit out there, such as trying to apply fashion to Twilight's Superpowered Evil Side.
  • Harmony Theory: Blaze's speeches are enough to make some fans suspect him to be Pinkie's descendant.
  • My Little Mages: The Nightmare's Return: Pinkie Pie, obviously, though being human somehow makes it seem more extreme.
  • In Ultra Fast Pony, Sweetie Belle admits that she doesn't live in the same world as the rest of the cast:
    Apple Bloom: Sweetie Belle, you're just living in your own little world most of the time, aren't you?
    Sweetie Belle: In my world, everything is made of sulphur!

Star Wars

Teenage Mutant Ninja Turtles

  • The Teenage Mutant Ninja Turtles fanfic The Long Walk has Leonardo musing on the Original Character Breech Loader, thinking about what it must be like to have to try to be normal. Breech Loader is a Cloudcuckoolander with a badly warped appoach to grasping normality, and a tendency to 'lose it' at the most inappropriate of times. As a quote from the story itself:
    Trying to be normal. He wondered what that was like; to try to be normal. Most people were normal, or normality came naturally. Or behaved however they saw as normal. Even most crazy people thought they were normal. Breech was trying to mirror their behaviour to be normal, and like a mirror, it came off wrong. Identical in every way, but somehow wrong; a facade, an illusion. What must it be like, to have to try to be normal?

Others

  • Always Having Juice has the alternate universe version of Metal Sonic, whose mental faculties appear to be malfunctioning. He believes he is "The Real Sonic", and frequently tries to prove it using stripes, the true meaning of Hanukkah, and the letter F. The viewers have caught on to his nuttiness, however, thus resulting in questions such as "what is your favorite flavor of frisbee?" (for the record, it's Satanic Death Christ).
  • Nappa of Dragon Ball Z Abridged:
    Vegeta: Nappa! No! It's a trick!
    Nappa: But Vegeta! Trix are for kids...
  • Enter Ken Finlayson: The titular character is viewed as one by the people of Norrisville due to his belief in the cryptozoological, the extraterrestrial and the supernatural but he really isn't. Still, many in-story believe him to be.
  • Marty McSuperfly in Captain Garlic's Let's Play of Icewind Dale 2. Watch out for him when he gets near the wisdom-enhancing items, or goes by the mushroom fields in the Underdark.
  • Oddly enough for a war story, Private Lenham Remer in The Legacy Of The Blood Ravens is a perfect example. When he's not kicking ass with his squad, he can be found musing about subjects like Space Bears, and if Space Marines can ride them.
  • Mega Man Recut has Dust Man and Metal Man.
  • Ignacio "Cio" Lumbre in Seven Devils is this trope, considering that when there was a fire, he tried to save the puppies before himself. Of course he did start the fire, and felt a little guilty.
  • Eric the Hedgehog from Sonic X: Dark Chaos embodies this trope. He's an Idiot Savant Talkative Loon who loves breaking the fourth wall and talks to his weapons like they have personalities. Deconstructed later on - not only is it revealed that he's physically brain-damaged due to imperfections in Maledict's cloning process, but he's fully aware that his thoughts aren't entirely normal and has hidden crippling depression as a result.
  • Major Raikov in Stray, a Metal Gear Solid fanfic, is "always the type who took sanity more as a suggestion," to the extent that Ocelot considers Raikov's Psycho Electro boyfriend to be the stabilizing influence in the relationship.
  • Demykins from Those Lacking Spines, a Kingdom Hearts fanfic, behaves in this manner, with a multitude of his lines as shoutouts to other media; when he doesn't quote from various works, he ignores the situation altogether.
    • Which is also the common fanfiction depiction of regular old Demyx.
  • Touhou M-1 Grand Prix has several boke that do this, to contrast with the straight man.
  • Viole from the "Towerof God" fanfic Dei Fabula; About to get burned by flames that can melt rods of steel in milliseconds? Ice-cream daydreaming time!
    • Not to mention that prior to that, his method of getting rid of a parasite that was mind-controlling the neighbourhood's friendly firebreathing Damsel in Distress was to french kiss her as opposed to simply sticking his fingers down her throat like his canonical counterpart did.
  • Momoko from Wedding Peach Abridged:
    Jamma-P: HEY, I DIDN'T WRITE THIS SCRIPT SO DON'T COMPLAIN TO ME!!!!!
    Yuri: Wow, someone needs a nap.
    Momoko: Is it me?
    Yuri: No. No, it's not Momoko.
  • The main character from Whispers in the Dark, a Percy Jackson and the Olympians fanfiction about the daughter of Thalia and Luke.
  • Yet Again: The Oogakari family. Dear sweet Jesus, the Oogakari family. They are possibly the nuttiest characters in the whole fic.
  • Tristan from Yu-Gi-Oh! The Abridged Series is a combination of a Cloudcuckoolander and a ditz. Almost every line that he gives is an illogical non-sequitur, such as his randomly given cry of "Burn the Witch!!" and "Take off your clothes!"
    • The sad thing is, these two examples are him being coherent in the context of the scene.
    • More extreme examples of his Cloudcuckoolandiness include "I like pudding!" and "I farted, it's funny!"
    • Marik is this and Poke the Poodle. His evil plans include pushing Yugi off a boat so that his hair will get wet and it'll take hours to dry, and borrowing Yugi's puzzle and not giving it back to him...for at least another 2 months. He also invited Dan Green to the Evil Council because he played a villain in one of the Pokemon movies, and seems to believe that there is a difference between killing someone and just 'destroying them a little'. And then there's the standard weirdness.
      Marik: By the way, Bakura, your costume could use some work.
      Bakura: ... what?
      Marik: I mean, I don't like to criticize, but it looks like your mother made that for you!
      Bakura: Marik, this isn't a costume. It's my clothes.
      Marik: Well, you could have done a better job is all I'm saying!
      Bakura: A better job of WHAT?
  • The Tightrope Girl's Haunted Mansion and the Hatbox Ghost incarnation is completely cloudcuckoolanderish.
  • The Somewhat Cracked Mind Of Uchiha Itachi:
    • Itachi. The title isn't just for show, but while Itachi is a bit off, he's far from the worst example.
    • Most of Konoha is filled with crazy people, to the point that Kankuro starts asking Baki what sort of messed up place he sent his team to.
    • Itachi's Iwa rival Deidara is even more off his rocker than he is — he just focuses all his crazy on explosions, to the point that all thoughts of defecting from his village die once he see his mentor, Onoki, the Tsuchikage, blow stuff up in a spectacular manner using his Dust Release.
  • In the Motion Practice series, which recasts various Marvel superheroes as lawyers, Wade Wilson is a legal aid lawyer with no brain->mouth filter and no dress sense.
  • In The Outside, Ryuuko is a deconstructed (and justified) version of this, as she's this due to being raised so sheltered and isolated by her older sister. To add to this, as a result, she views anything that isn't her house to be a different world and imagines her sister has always existed and that "everything materialized around her", however, she's aware that her views make little sense (she calls her ideas "absurd as hell") but, as she says, has plenty of time alone to her thoughts (turning into this to cope with her situation).
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