Ren and Stimpy and Aeon Flux. Jungle Wa Itsumo Hale Nochi Guu and Ebichu the Housekeeping Hamster. This dubious coupling of both a pair of bizarre, twisted American cartoons and a pair of humorous, absurd Japanese anime productions constitutes all of my personal "Top 5 Strangest Most Fucked Up Cartoons Ever"... except for the number one spot. There is only but one mishmash of television friendly half-hour animation I find more mind-altering, intense and otherwise disturbing than these four... and it calls itself:
"Oh! Super Milk-Chan"
...This Oh! Super Milk-Chan is a crazy, crazy anime that aired from January to April 2000. Evidently, there was a bunch of shorter five minute proto-type clips know as simply "Super Milk-Chan" that aired as part of a cartoon variety show. It gathered enough popularity to form its own independent series of episodes not unlike Pinky and the Brain.
Combining defining elements of the Powerpuff Girls (such as cartoonish, bold lines for the animation and law enforcement being placed in the hands infantile chicks by government figures) with witty satire (all of which is deep Japanese pop-culture references that I can't even begin to understand), Oh! Super Milk-Chan is quite a trip. It wasn't meant for an American audience, but it nevertheless provides me with much more amusement than its target Japanese audience probably gets out of it.
Oh! Super Milk-Chan follows the snail-paced misadventures of the constantly drooling Super Milk-Chan (pronounced kind of like Su-pa-ru Mi-ri-ka Cha-n) as she serendipitously saves the day (sometimes), protects truth and justice (sometimes) and cracks obscure jokes about 1970's Japanese culture figures (always).
Milk-Chan's reddish, space age attire looks like the bastard child of a Santa Claus costume and The Jetsons' wardrobe. She has a wonderfully obnoxious sing-song voice that extends every vowel. She has a habit of yelling "Baka tsura!!", or, in English, something approximately like "Idiot face!!". Despite being very cute and girlish and infantile, her naivete is ironically mixed with ruthlessness and cruelty... but in a very, very funny way.
She lives with two abnormal friends: Tetsuko the robot and Hanage the... weird thing. Tetsuko, who is a bottle shaped robot maid, has an extremely disturbing electronic voice. And then there's the insightful but ugly little creature named Hanage that resembles a Mr. Saturn. But then again, unless you've played a certain bizarre mid 90's console RPG, you probably don't know what a Mr. Saturn looks like. Don't worry too much. Just know that... Hanage looks freaking weird. He hops in the air and says "Peuuuuuuw!" and has long introspective soliloques.
Among the other characters are The President, The Landlord and Dr. Eyepatch. The President is a direct successor to the Powerpuff Girls' Mayor of Townsville. He's a bumbling official that constantly calls Milk-Chan to correct his mistakes and do his job. The Landlord is an oddly shaped man that tries to collect rent from Milk-Chan every episode, but is easily tricked by her schemes. Dr. Eyepatch is a grinning, ghostly figure that supplies Milk-Chan with inventions and supplies a la James Bond's "Q".
To add to the confusion and madness, bizarre live action "video essays" are inserted randomly between scenes. These homely recordings of park benches and cats sleeping on sidewalks and people walking their dogs are accompanied by calm, self-help video style atmospheric music and a soothing young woman's voice reading strange and funny over-the-top prose/poetry stuff that makes generalizations about time and love and death and whatnot. I've included one below, but the text itself doesn't truly convey the hilariousness without the completely unrelated video:
Video Essay: Mushrooms Browned in Butter
By Maitake Akiko
I got up late today, how will I spend the afternoon? Just listening to music? Or cooking my favorite dish: cream stew? Stewing meat carefully with love for you... My room will be fragrant with happiness. I got up late today, how will I spend the afternoon? Oh? Someone is at the door? A new dust mop from the sweeper company? Oops! I must wear my wig now!
Produced by: Space Shower Network and Suplex
Animation by: Studio Pierrot
Director/Design/Original Creator: Hideyuki Tanaka
Screenplay: Motoki Shiina
Animation Director: Takahiro Ohmori
Watching several episodes
http://www.supermilk-chan.com/ (Highly recommended and wacky. Informative English section. The above credits were gleaned directly from this site.)