Here for your information and enjoyment is a rundown of the details.
Winnie the Pooh
Pooh is either a bumbling idiot or a pothead. I'm leaning toward the latter, as evidenced by his occasional moments of philosophical clarity and (most notably) the fact that he constantly has the munchies. He sits around all day dimwittedly contemplating existence and wondering when the Hundred Acre Wood will be getting a Taco Bell.
Piglet
Suffers from paranoia, delusions, a litany of phobias, and is possibly schizophrenic.
Piglet is a hot mess.
Tigger
Tigger's a cocaine user but doesn't want his friends to know. He shows up happy, excited, energetic--literally bouncing with glee. Usually he quickly buggers off to go do some more coke but sometimes he sticks around for a while. The longer he's around the more confused, irritable, and frustrated he gets.
This is because Tigger is coming down from his high.
He doesn't want all of his friends to know what he's up to, so he never does it in front of them. This means than anything more than a few hours around his pals leaves him itching for another bump.
Rabbit
Rabbit wears an apron, meticulously tends his garden, and constantly fusses over things like his dinner parties, his silverware and dishes, the cleanliness of his house, and whatever he's currently cooking.
Rabbit is a closeted homosexual.
However, his uncontrollable outbursts when someone gets in the way of his obsessions or puts something out of order suggest that he's not just bitchy, he suffers from Obsessive-Compulsive Disorder.
The magnitude of its severity is hard to assess though, as he often exaggerates it to cover the fact that he is, as mentioned earlier, a closet-dweller.
Kanga
Like Pooh, Kanga is a major stoner.
Even more so than Pooh (who will occasionally articulate his frustrations by saying "Oh bother"), she is extremely mellow. As chaos constantly and inevitably erupts around her via the other nutjobs, she calmly asserts that everything will be fine and everyone should just like, keep it cooool maaaan.
We know what's in that pouch, Kanga.
Gopher
Gopher, like Tigger, is constantly hopped up on stimulants. He's always working, always energetic, never stops, and never tires. Unlike Tigger, however, he lives underground and can thus hide his substance abuse better.
What exactly he's on is uncertain; meth can be ruled out as his teeth are still in good condition. Whatever that old lady in Requiem for a Dream was using... Probably that.
Owl
Owl is actually quite sane, and once you understand his situation you can't help but pity him. The problem is that he's an idiot.
He has to live up to the "wise old owl" stereotype that is projected onto him by his friends, so he constantly spouts gibberish at them, misinterpreting things that he doesn't understand and presenting his word as gospel.
His friends, aware of their own ignorance and seeing him as "wise," believe everything he says.
These BS sessions always backfire, causing problems for himself and everyone else. A notable example of this was the incident where Christopher Robin went to school, which Owl misread as "skull." He then sent everyone on a wild goose chase to rescue Christopher, nearly getting them killed.
The sad part of this is that Owl knows he's full of shit. Even when his attempted highbrow babblings get them into trouble he must carry on the charade lest the others realize what a dolt he is. This is why he's one of the most rarely seen characters. He avoids the others for fear that they'll ask him questions for which he'll need to make up answers.
He's an idiot and a fraud and he hates himself for it.
Christopher Robin
First of all, where the hell are this kid's parents? He'll mention them from time to time but we never see them. Assuming the Hundred Acre Wood is aptly named, that's a pretty big tract of forest for some little kid to be mucking about in unsupervised.
Add to that the obvious fact that he's delusional (talking to toys all day) and it's clear that his parents' neglect has taken its toll on his emotional, social, and mental well-being.
He likely won't make it to adulthood before he's committed to an asylum.
Eeyore
Everyone is quick to diagnose Eeyore with depression, but I disagree.
This, ladies and gentlemen, will be the topic of my next post.
Until then, good luck watching Winnie the Pooh without thinking about this.