"Captain Eeyore"... might just be one of the greatest things I have ever seen.
Never intended for the eyes of people who are not Disney Cast Member Cyborgs, this little slice of happy was created to be the highlight of a cast party. It's since become a cult favorite that has recently gained some new fans thanks to the wonderful Walt Dated World website posting it on Facebook as a tribute to Michael Jackson. It may be the best tribute I've seen so far:
It's a little bit funnier if you know the back-story (here care of Jim Hill Media), particularly the horror stories centered around that walking design flaw better known as the original Pooh costume. (Anyone in the suit was completely unable to use their arms as, unlike in the film, you are not allowed to break character for anything. Think about that for a minute.)
If you're the impatient type, skip to Part Three, which parodies most of the "Captain EO" scenes you actually remember and has Eeyore dancing.
Now, a while back, I was finding and posting several other weird Disney film and television clips from my past that I'd found online. I was hoping to eventually build to the weirdest Disney cartoon I remember seeing but it slipped my mind. Well, now is the time. Now is the best time! Now is the best time of your...
The weirdest Disney thing (of which I am currently aware at least) is a cartoon called "Plutopia":
Actually, I will make one comment about this cartoon, and it is specifically directed at all the "Oh noes, think of the children" types out there. I saw this cartoon a lot as a little kid. And even back then it freaked me out a little, but I was unable to put into words exactly why. (Until I watched it again in college and realized that Pluto is fantasizing about being overfed by a sadomasochistic cat.) So dark and/or adult things in cartoons will not scar a child for life or anything because it will probably go right over their head. Usually.
Also, the "bone well" is creepy if you think about it.