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. That's pretty great. He's also known to invertSanity Slippage, sounding increasingly normal the more trouble he's having with a game.
Doug: Lewis, do you think the characters in your show are real? Lewis: Oh Doug, I'm not deranged. Only Harvey and Pollo are real.
Deconstructed with Rebecca from Demo Reel. She really isn't all there, but it's half-faked to get more work as an actress, she drops all "kooky" when it comes to feminism, and the abuse she suffered is the cause of at least some of it.
Chuck Tingle - a lame Midwest dad who writes surreal erotic fiction about dinosaurs, unicorns and 'getting pounded in the butt by my own butt', and has an ongoing feud with his next-door neighbour. A Small Name, Big Ego with a PHD in massage who believes in being a 'true buckaroo' with one's 'hard buds' and that 'love is real for all who kiss', he has his son Jon edit his baffling internet posts, started a political campaign to get Channing Tatum elected president under a belief that Barack Obama was attempting to limit the flavours of ice cream to chocolate, vanilla and strawberry, and refers to his enemies as '#antibuckaroo devilmen'. Most apparent in his hand-drawn vlogs, where he reviews Star Wars villains such as 'Dark Vader', 'Grims Reaper' and 'Jon Hunt' and posts details of his attempts to humiliate his next-door neighbour by dressing as 'Mike Myers the Batman'. According to an AMA by his son/editor, Chuck is an autistic savant who suffers from schizophrenia and is indeed as strange as his online persona might suggest.
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.
The title character of 80's Dan is like this in how he treats The '80s compared to modern day.
Beyond the Impossible: After living on Earth for a full year, Torn hasnít picked up the meaning of the most basic things (he didnít know what Earth or North were) just because he wasnít paying much attention. Bob Null qualifies as well: he thinks the best place to keep the Heart of the Universe is in the fridge:
-You put the most valuable device in the world in the fridge Ė Noriko repeats skeptically. -Yeah. -Iím afraid to ask why. -Nobody would search there. Unless it was a hungry thief or something. -I knew I had reason to be afraid.
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.
Coma: Fly fishermen at thirty paces! Invert the muskrat!
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, turns out to be a metaphor for one of the main messages of the entire epic series, and is called back to in the Grand Finale.
"Weird" Jimmy and Lionel of Chad Vader. This installment of in-universe training videos particularly highlights many of the hallmark idiosyncrasies of the former:
Jimmy: [instructing viewers on the proper techniques imperative to mopping] "But even more important than your 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."
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.
Ginny from Dangerous Lunatics quite definitely qualifies. Turns out she actually can make walls melt, though.
"My daddy makes toasters for a living! I like to look at the MOON!"
Tyler of Epic Meal Time is often seen goofing around and picking his nose, but ever since he left the show over disputes. Prince Atari took over.
Fictosophy: In "Jedi Coworker," Tom is so much of a Star Wars fan that he organizes a Jedi Temple, not realizing that Steve, his coworker, isn't interested.
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).
Every character from Friday Night Cranks has been this at one point, but Barney, Brendan, and Michelle probably qualify best.
In The Gamer's 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):
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!
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.
Clara from The Guild could be considered one as well.
June Diane Raphael, in her role as one of the hosts of How Did This Get Made?, has a reputation for rather off-the-wall questions and trying to piece together very bizarre facts from even more bizarre movies. Even in episodes where June isn't on the show, Jason Mantzoukas may respond to a similarly absurd statement with, "Well, you see, June..."
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.
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.
Just like his real-life counterpart, David Lynch, The John Dredge Nothing To Do With Anything Show's "partly acclaimed avant-garde film director and weather forecaster": Amongst other things, he made a ten-hour film about a talking lamp, followed by a sequel about a talking bell. Later, he transformed his kitchen into a room for storing gold bars.
John: Why, it's amateur film director and avant-garde weather man, David Lynch. If you don't mind me saying so, David, you look like you've been dragged through a picket fence backwards. David Lynch: That's one of my hobbies, John. John: Well, apart from being dragged through a picket fence backwards, what have you been up to recently? David Lynch: I've been nailing things to other things, John. John: Why? David Lynch: I don't know. I suppose I'm just naturally gifted at that sort of thing.
Julia's boss Justin Credible from KateModern, 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).
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.
Rainbow Dash from My Little Pony: The Mentally Advanced Series, particularly in the Spin-Off series Rainbow Dash Presents, in which she reads famous/infamous fanfics, with "reads" being used only in the broadest of terms. One particular example is the infamously Grim DarkCupcakes, which is turned into more of a romantic comedy between Pinkie Pie and Rainbow Dash (mostly due to Rainbow Dash skimming it over breakfast) and involves a conversation between Mrs. Cake and Pinkie Pie about her actions in the basement. Which is more about Pinkie not working when she's supposed to and cluttering the basement with the souvenirs of her heinous crimes.
Big Yamma from Omni Bleach Abridged; He basically does every thing on a whim, from requesting an execution because he wants to see it, to buying a gold, Gem Encrusted Twilight Sparkle cane on in impulse, to calling a meeting out of boredom. It's rather horrifying and speaks leagues about the incompetence of the Soul Society's Government.
Random Assault: With some of the jokes, bits and tangents Mitch has come up with, he might as well be.
Mitch Gunter. The following quote is all of the explanation required.
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.
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.
Welcome to Night Vale: Similar to the entries for The Addams Family and Green Acres, everyone but Carlos in the town of Night Vale. Cecil seems like the worst offender, as the narrator, but a lot of his stories imply that the rest of the townspeople are even worse.
TV Tropes: For more viewing pleasure, please see our delicious, nutritious Wild Mass Guessing pages for all your cloud-cuckoolanding needs.