Cloudcuckoolander/Web Original

Web Animation
""Say, you got a girlfriend? Well, what if your girlfriend was a wooden spoon and an orange plastic bowl? That'd be really weird, man. What kind of screwed-up kid are you? We don't recruit your kind! Get out of here!""
 * The Homestar Runner universe has a number of these:
 * Homestar Runner is usually The Ditz, but his energetic, active stupidity often results in some surreal dialogs (or monologues).


 * Or the way he talks to the movies in the theater. Not as in, "Oh no don't do that!! He's right behind you!", just small talk to the characters. Sometimes about a salad he plans to make. "Yeah, I figured I'd just cut up some iceberg lettuce, throw some tomatoes on there, maybe a little catalina.Nothing fancy, nothing fancy..." Homestar is often naive to the world around him, so he often needs Pom Pom to help him... too bad Pom Pom is The Unintelligible.

"Homestar: (upon walking into a cemetery) Oh man, Pom Pom, this is gonna be so great! First, we'll hit Space Mountain, then over to Mr. Toad's, then Tom Sawyer's Island, and don't forget, we parked in the Goofy lot!"

"Homsar: Oh no! You shanked my Jengaship!
 * Homsar is the Lord Mayor of Cloudcuckooland. He communicates largely in non-sequiturs with only the flimsiest connection to the topic at hand, and his disconnection from reality is so strong that he breaks the laws of physics (by levitating either himself or his hat) every time he speaks. He also somehow managed to survive having a Heavy Lourde dropped on him.

Strong Sad: I shanked your Jengaship? We're playing Connect Four."


 * According to episode 2 of Strong Bads Cool Game for Attractive People, Homsar is apparently just speaking his own incomprehensible language rather than being a true Cloudcuckoolander. Strong Bad can temporarily understand Homsar, who is actually quite articulate to those who can understand him. To anybody else, any conversation those two have ends up as a series of confusing ramblings.

""Home Lawn, Escrow, Re-Financin'; you name it, we've got it! Come along down for a free canceltation with one of our handsome-talking experts. (Points at an empty chair.) One o' them said they'd buy me lunch, but I don't see nobody taking me to Chick-Fil-A.""
 * Cardgage, a creepy-old-man-with-a-combover version of Strong Bad who constantly mispronounces "invents" new words and refers to men (and robots) as if they were ladies, among other things.

""You better believe it's new Fluffy Puff Malloween orange and black flavored marshmallows! "They Taste the Same, but Loo--" [violent coughing] Sorry. Must've got a toenail caught in m'throat!"
 * Marshie is just dadaist Nightmare Fuel.

"Marzipan: Coach Z, might I ask why you're buying up all the "great for baby" items?
 * Coach Z has his share of weirdness:

Coach Z: I'd prefer that you didn't..."

"Strong Bad: Hey, Strong Mad! What, uh... What's my favorite movie?
 * Strong Mad has his moments, both because he speaks in a loud voice and because, as Strong Bad points out, he has "a pretty tenuous grasp on the English language." Example:

Strong Mad: GARBLEDINA!!!!"


 * Strong Mad also likes to make dinosaur-themed art (i.e., an MS Paint drawing, a claymation film) and made a "portrait" of Strong Bad out of glitter and macaroni. And, as seen in Strong Bad Email #58: "dragon" (the email from whence Trogdor originated), instead of drawing a picture of a dragon, Strong Mad carves the word "DAGRON" into a table, which Strong Bad doesn't seem to mind.

"Marzipan: Oh, these [crayons] don't actually color anything, so no "life blossom" feels more special than the others."
 * One can safely say that there's also a Cloudcuckoolander Ball being tossed around constantly in the Homestar Runner universe, with Bubs,Strong Bad and Marzipan being prime recipients for it.

"Kiki: I thought this was a library. Aren't there supposed to be books?
 * Fred of Fred the Monkey.com acts this way on occasion.
 * Red vs. Blue's Caboose started off as a profoundly stupid recruit, but between Flanderization and mental trauma from possession by a rogue AI, he quickly loses much of his grasp on reality. He thinks his commander is a gay robot, plans to use his Purple Heart and future medals to build a purple person ("and we will be best friends"), is in love with a tank, and good friends with a bomb. Journeys to the center of his mind reveal that it's inhabited by wildly inaccurate avatars representing the rest of the cast: Red Team's leader talks like a pirate, the one in pink lightish-red armor is a girl, and Blood Gulch's newest arrival is "from the part of the plane that crashed on the other side of the island." Naturally, Caboose is one of the most popular characters. Caboose's voice actor Joel Heyman described him as "the only character who knows they are in a video game." With this in mind, Caboose's actions make a lot at least a little more sense.
 * The world of the Charlie the Unicorn shorts appears to BE Cloudcuckooland.
 * Daffy Duck, the early years. 'Nuff said.
 * Tori of Fairy Foxes. Example in episode 4:

Tori: (upside down) No silly, the books are below you!

Mimi: No, Tori, that direction is up. You're saying that they're above you.

Zoey: Wow... the books are floating.

Tori: Yay!"


 * Salad Fingers is a somewhat creepier version of this trope.

Web Original
"Ronove: There's something important that I must share with you before we begin our march. Something terrible happened last night, something that truly, should I say, PISSED ME OFF! Here's what happened. There's an inn in this city that has this amazing strawberry cake, but the last FIVE FREAKING TIMES I've tried to order it, they don't have it! This is clearly unacceptable! If the king can't eat his daily strawberry cake... man, if that isn't god-moding, I don't know what is! I also have another announcement to make: henceforth this day of the week shall be officially known as Cake Day! Strawberry cake will become our national food, and we'll build bakeries and stuff everywhere so that you, my dear subjects, can have your daily dose of this excellent dessert!"
 * In The Gamers Alliance, the amnesiac wanderer Ronove really doesn't understand what's going on most of the time. For example, when demons are about to invade the Sarquil capital during the Vanna arc, he decides to go on a picnic outside the city walls and convince the demon horde to surrender by offering them cake. When he is forced to impersonate King Marcus, his rousing speech to the Grand Alliance's army goes well at first until he decides to put his own spin on it (which involves his favourite dessert):

"Mitch: Dog eat dog. Dogs don't eat dogs, they eat birds and cats and Kibblebits if they have a family. Those words are silly. But I would have gotten that right if that silly glasses boy hadn't answered before me. Yes, I would have gotten it right."
 * Survival of the Fittest
 * Mitch Gunter. The following quote is all of the explanation required.

"Coma: Fly fishermen at thirty paces! Invert the muskrat!"
 * Sven Kekule from V1. V4 gives us Cisco Vasquez, Maria Graham and Lily Ainsworth, amongst others, including Albert Lions, at least following his adoption.
 * Milo Taylor.
 * Brigadier-General David Adams from The Program. He started reciting impromptu poetry during an announcement. (He's supposed to be updating the kids on who's dead)
 * The Mad Scientist Wars. Well... Everyone, at some point or another. Particularily if in the middle of going Mad.
 * Shiny Objects Videos: Most characters have shades of this, with Nathan as the Only Sane Man.
 * The titular character from John Dies At the End. His antics include: Creating an elaborate system of coded phrases that sound even more incriminating than the messages they are intended to conceal; Leaving random and often inappropriate comments on customer's files at his work; Threatening to "dick-slap" random strangers; doggedly reusing the same tired pun multiple times throughout one fight; and refusing to abandon a gimmick which he thought up several years prior at four in the morning while drunk. His status as a Undisclosed's resident Cloudcuckoolander is one of the main reasons he is able to blog about all the supernatural stuff that happens to him without bringing down The Masquerade.
 * If there was ever any doubt as to whether John was truly the god of Cloudcuckoolanders, it disappeared with this update.
 * Speaking of Cracked; Daniel O'Brien, or at least his fictionalized alter ego, has tried to do things like challenge Google to a death race and believes that establishing dominance is an important part of cooking.
 * Some of the op-ed columnists at The Onion would easily fit this trope.
 * Julia's boss Justin Credible from Kate Modern, in a way that veers back and forth between creepy and amusing. To give you some idea, he puts his clothes on backwards, makes his office in a toilet and plasters the walls with photos of Lee dressed as a jockey and Julia in a bikini, "forgets" to pay his employees and keeps coming up with bizarre ideas for TV shows (all of which are awful).
 * The Wallflower Report is a blog written from the point of view of (fictional) Cloudcuckoolander Ariella Rasputin Wallflower. Her two most recurring 'landerisms are her disbelief of trees (atreeism) and her paranoia concerning squirrels.
 * Internet wrestling parody Brawlers On A Budget has Coma, formerly half of the Head Trauma Boys. Due to taking too many chairshots, he communicates entirely in non sequiturs, and is known to wear such outfits as a toga with a tutu. His current tag team partner, Hallucination Boy, sees everything as oncoming trains.

"Booya: It's like shooting fish in a barrel. Except instead of a gun you're using dynamite. And the fish aren't particularly smart either. With a bad sense of pattern recognition. And the dynamite has some sort of fish seeking technology.
 * The lines from "Booya" in a Let's Play of UFO Aftermath, which are more often than not followed by other members of the group...well...

Everyone Else: ..."

"Jimmy:"More important the the grip is listen to your mop, because mops talk. They'll tell you where the dirtiest parts of the floor are and the dirtiest parts of your soul.""
 * Ash from Hey Ash Whatcha Playin qualifies.
 * That Guy With the Glasses
 * Chester A. Bum. To sum it up in 12 words-"CHANGE! YA GOT CHANGE! Oh, c'mon, help a guy out here...CHANGE!"
 * Nella also gets into this territory sometimes, especially when My Little Pony is involved.
 * Ask That Guy With the Glasses is a quite psychotic version of the trope.
 * The Nostalgia Critic is fooling nobody when he tries to tell people that he lives in the realms of the real world.
 * Jew Wario, in kind of a Mayor West-ish way.
 * Benzaie
 * Bennett the Sage, who once creeped out Ask That Guy With the Glasses.
 * In spite of his name, Angry Joe leans more toward this.
 * Weird Jimmy and Lionel from "Chad Vader". An example from one of Chad Vader's Training Video, Jimmy talks about how to mop the floor.

"Codex: He's in my bathroom. Pooing evidently.
 * Severin from Fragile is very much a Cloudcuckoolander. (Especially in the first bit, where he's at the grocery store, talking to himself about soup cans.) Though, this is kind of explained by his mental disorders (Asperger's Syndrome, although he claims he's also got hypomania).
 * Broken Saints has Masayuki, a slightly off-kilter young egg farmer who the aged Shinto priest Kamimura encounters early on in his journey. He relates to Kamimura a lesson about eggs and poop that his father once told him, which, naturally,
 * Clara from The Guild could be considered one as well.

Clara: Oh. I hate poo..."

""My daddy makes toasters for a living! I like to look at the MOON!""
 * Ginny from Dangerous Lunatics quite definitely qualifies.

"David Bowie is the Goblyn King! He does not age!"
 * This review plays with the trope. One of the two reviewers makes increasingly nonsensical comments, punctuated with ones that are actually insightful. In the end it turns out to have all been due to Iji's scrambler which he left running after a previous review.
 * For more viewing pleasure, please see our delicious, nutritious Wild Mass Guessing pages for all your cloud-cuckoolanding needs.
 * Raocow, whose Lets Plays are filled with some of the most surreal non-sequitur commentary you'll ever hear. They're filled with happiness and mashed potatoes.
 * Demyx from Demyx Time:

"Zack: Do you guys keep your dead cat in a box, too?"
 * King Humphrey VII/II of New Albion from the Chaos Timeline. While living in a modern world, he stills claims he's the rightful ruler of Britain, Canada, the other former colonies and big parts of Europe.
 * Every character from Friday Night Cranks has been this at one point, but Barney, Brendan, and Michelle probably qualify best.
 * Damian of makemebad35 fame on YouTube. Most, if not all, of his videos involve him doing and saying some of the strangest shit even by YouTube standards. There are a few times he plays a bit of a straight man type, but even then he's still a bit off.
 * Ranger in Comic Fury Werewolf has been known to be this. He thinks it's getting worse.
 * Most of the Theatricans in Theatrica have sunk into Cloudcuckoolander territory, mainly as a result of their ancient history and isolation.
 * The author of My Opinions On Every Pokémon Ever counts as one.
 * Zack from Echo Chamber. Is he trying to be funny or is he actually this stupid? The world may never know.

"[Talking about a fly]: He was like a rainbow..."
 * YouTube personality Toby Turner, A.K.A. Tobuscus. Some of the verbal/mental tangents he goes on during his videos must be seen to be believed.
 * Supervillains Simon bar Sinister and his twin sister/lover (yes, its that sort of relationship) Penny Dreadful, from the Global Guardians PBEM Universe. They'd be seen as a lot more comical than they are if they weren't also Axe Crazy murderers.
 * Tom Milsom


 * The Gungan Council has Spencer Jacobs and Io Akima
 * Dionysus in Greek Ninja.
 * Title character Thalia in Thalias Musings. Wedding peacocks, nuff said. Also she glued herself to her chair.
 * The title character of Eighties Dan is like this in how he treats The Eighties compared to modern day.
 * Egoraptor, the creator of the Awesome Series and Girlchan in Paradise.
 * Sgt. Schwartz of Skippys List. The Loonie is apparently in the Army. This troper is unsure if that's awesome or terrifying.