Homestar Runner is usually The Ditz, but his energetic, active stupidity often results in some surreal dialogs (or monologues).
"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!"
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 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.
Homsar: Oh no! You shanked my Jengaship! Strong Sad: I shanked your Jengaship? We're playing Connect Four.
According to episode 2 of Strong Bad's 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.
Senor Cardgage, a creepy-old-man-with-a-combover version of Strong Bad who constantly mispronounces "invents" new words (which, as Strong Bad says, are "almost one word and not quite another") and refers to men (and robots) as if they were ladies, among other things.
"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."
Marshie is just dadaist terror personified.
"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!
Coach Z has his share of weirdness:
Marzipan: Coach Z, might I ask why you're buying up all the "great for baby" items? Coach Z: I'd prefer that you didn't...
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 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.
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.
In the Teen Girl Squad series, there is The Ugly One, who is a mindless follower of Cheerleader and is slightly more eccentric than the other girls. She is readily included in the Squad's Cheerleader-led activities, such as shopping, spring break vacation, and jumping into a lion's mouth.
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, as journeys to the center of his mind reveal, has wildly inaccurate beliefs about literally everyone else he comes in contact with. He also has a bizarrely good intuitive understanding of AIs and electronics and general—even if he has no idea on a conscious level how any of it works, to the point of believing electricity is invisible magic.
Tori of Fairy Foxes. Example in episode 4:
Kiki: I thought this was a library. Aren't there supposed to be books?
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.
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!
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):
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!
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.
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 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.
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).
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.
Coma: Fly fishermen at thirty paces! Invert the muskrat!
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...
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.
"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."
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, 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.
Clara from The Guild could be considered one as well.
Codex: He's in my bathroom. Pooing evidently.
Clara: Oh. I hate poo...
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!"
This reviewplays 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.
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.
Most of the Theatricans in Theatrica have sunk into Cloudcuckoolander territory, mainly as a result of their ancient history and isolation.
Zack from Echo Chamber. Is he trying to be funny or is he actually this stupid? The world may never know.
Zack: Do you guys keep your dead cat in a box, too?
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.
Sonty Mick, from These Web Comics Are So Bad. He harshly judges every webcomic based on bizarre standards that never get explained to his readers.
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 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.
Elrich, a setting in The Wanderers Library, is full of them, but the living fruit are on a whole new level.
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.
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.