The Amazing Digital Circus: Having been in the titular place for the longest has severely damaged Kinger's mind (though not to the point of abstracting): he's paranoid and often hides in a pillow fortress, is obsessed with the idea of "an insect collection", freaks out often because he forgets the presence of others, and brings out topics and events which are completely irrelevant from whatever's currently happening.
The world of the Charlie the Unicorn shorts appears to BE Cloudcuckooland, and Pink and Blue are the major players, if convincing Charlie to join them on bizarre quests just to mess with him is any evidence..
DC Super Hero Girls: Harley Quinn does take after her previous incarnations in this regard. Whether it's playing pranks, making awful plays on words, or being Innocently Insensitive, she's still a loon.
Old / Senile Gothi from Dingo Doodles - Fools Gold, amongst things she's done is - make a potion that melts people and decide it just needed more nutmeg, stole and kept 28 ducks, when everyone else got gold and jewels as loot she took a rock instead and called it Dwayne, was random enough to be used as a distraction to confuse a person the rest of the party needed to sneak past. Once she regains her youth and lucidity she loses most of this but some of the personality is still hidden inside - like the time she set locusts on a market to make them flee a dangerous situation.
DSBT InsaniT: Taylor, the electronics store owner, is definitely an oddball, and alters between being helpful and annoying.
Giovanni Potage, aspiring supervillain, who is introduced having willingly joined a pyramid scheme on the theory that it being a pyramid scheme meant the people running it were serious about being evil. Despite being a great cook, he has next to no sense of taste because he ate a coal at a family BBQ on the theory that it was "forbidden candy" and experimented with his soup-based powers until the result was a permanent scar.
Rick Shades is prone to saying morbid and disturbing things with tremendous cheer, thinks being purple is worse than being dead, and his default reaction to any emotion is screaming. His first surface friend, Phoenica, is a little more sane but still does things like paying extra to have her business cards both be edible and function as flares.
The bartender at Redwood Run sells "alphabet soup" with 22 letters, including a new one he invented. He also uses this to load his shotgun. Which is thrown to him by his cat. Also, he's using a shotgun while blind.
Bartender: I USED TO BE A GOVERNMENT EXPERIMENT! Ramsey: Yeah, that sounds about right.
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. Tori: Yay!
Jimbob in GEOWeasel occasionally goes off tangents and snaps back with non sequiturs. Nar is usually The Ditz, but in one case can apparently understand Jimbob's outbursts. At one point, Weas is able to read minds. Two characters have thoughts in their normal voices, but Jim just has backmasked music playing in his head.
Nar: Hey, Jim, how's the weather? Jimbob:Apples and cream pie! Nar: Yeah, it does look like it's gonna rain.
Race X Shock Trooper Kiss Kyur Mub Mub Ka Mub Blis Ka (KKMMKMBK for short) is known to be a weirdo even by his transdimensional species' standards. For us, he's a profoundly bizarre creature that barely even understands how humanity (or reality) works and still tries to befriend humans for whatever reason. For them, he's still a profoundly neurotic and possibly cowardly individual that fled Black Mesa out of claustrophobia and got lost in a strange dimension because of it.
Po Ta Ter the Pit Worm is another example, being extremely hyperactive, childish and prone to rambling about the "Gene Worm", some kind of deity he wishes to summon and continually fails to do so. We don't know if Pit Worms are generally like that though.
Happy Tree Friends: Nutty puts the 'psycho' in Cute and Psycho! Most of the time, he isn't even in reality. He views everything that slightly bears a resemblance to candy as the very item he desires and he doesn't really pay attention to the carnage around him, even laughing at the deaths of himself or others.
Lumpy also qualifies as he tends to be off in his own world, sometimes not even noticing the deaths he himself is inflicting on the other characters.
Downplayed with Bee-Lzebub in Helluva Boss: While she is capable of being quite lucid by normal standards, a conversation with her can be pretty bewildering when her mind is racing around quickly in different weird directions.
"Reminds me of the first time I saw Satan without a shirt on. I was like, ooh! Boy! You are hot as hell. But then I wanted to die, because it was so awkward because he's more like a brother to me. You know? But not actually my brother. So, I guess... It was fine. I could hit that..."
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!
"myths & legends" indicates that Homestar thinks Pom Pom is his dog, literally.
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. Also, in "Marzipan's Answering Machine Version 17," he talks about how he's more articulate on the phone (a Call-Back to his message in Version 5, one of the only non-SBCG4AP instances where his talk does make sense) and knows that when he hangs up, he'll go back to spouting garbage.
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, the unnervingly-manic mascot for Fluffy Puff Marshmallows, is just dadaist terror personified.
Marshie: 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.
Big D from Hunter: The Parenting is a terrfyingly experienced Hunter of Monsters, but he's also completely disconnected from reality. He thinks landlords shouldn't exist because everyone should live in castles, apparently considers golfers and groundskeepers supernatural beings to hunt, and hunts vampires while high on DMT.
All right, whatever, I don't respect time, it's an odious concept, NOW LISTEN UP!
If the Emperor Had a Text-to-Speech Device: Warp's clearly been hard on Kaldor Draigo's mind. Let's just say that he can leap from talking about stealing Karamazov's throne into talking about tiny men coming out his beard (kill them all!) and leave it at that. His current company in the Warp don't really qualify him as sentient anymore.
Exploited by Taco. Nonsensical sayings? Seems appropriate enough. Utterly bizarre behavior? Okay, fair dues. Doing all of this to be regarded as Too Quirky to Lose? Turns out that she was Obfuscating Insanity all along.
Lightbulb is a rather quirky girl who sees nothing wrong with eating sticks and yarn, or creating a cookie pizza.
Tissues is not far either. He thinks Oatmeal Raisin cookies are the reason for global warming! Which is also the reason he hates them.
Most of James Lee's videos are just him muttering to himself (and the viewer) about his trains of thoughts, and he will often say or do weird and creepy things. Even when he's interacting with other characters, he still behaves like a complete weirdo.
The eponymous Kaguya Luna has odd mannerisms such as having the odd fascination in guessing the blood types of her viewers and making videos consisting of her singing, shouting at the top of her lungs, or doing tongue twisters.
In Lackadaisy, lead booze-runner Rocky is flighty enough to turn vitally important lookout duty into an opportunity for an impromptu Fantasy Sequence poetry rehearsal, but also improvisational enough to turn being cornered in a quarry into a dynamite-hurling maniacal spectacle of a Construction Vehicle Rampage levelled against rival gang members...that is also an impromptu poetry rehearsal.
Rocky: *gesturing with lit dynamite* Come gather, gather all around. * a gunshot ricochets off his perch on the bucket of a steam shovel* Rocky: *screaming while hurling the dynamite* See them rain their fire down! AHAHAHAHA!
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 A.I.s and electronics in 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.
, is himself a Cloudcuckoolander