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=== '''Winnie The Pooh''' ===
 
{{quote| ''[[Catch Phrase|Oh bother.]]''}}
 
The title and main character. A naive and soft-spoken teddy bear who lives in the trunk of a tree under the name of 'Sanders' written over his door. He utterly loves "hunny" and his home is filled with "hunny" pots of all sizes.
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=== '''Christopher Robin''' ===
 
{{quote| ''Silly old bear.''}}
 
The only human character to appear in the books, Christopher Robin is the storybook allusion to the [[Real Life]] boy Milne wrote the stories for. He is a young boy who spends time with his stuffed animals in the distant Hundred Acre Wood and acts as a mentor and leader most of the time. Later in the series, he attends boarding school.
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=== '''Tigger''' ===
 
{{quote| ''Bouncin's what Tiggers do best!''}}
 
Hyperactive stuffed tiger with a fondness for bouncing. Known to grate on others' nerves (especially Rabbit) with his tendency to bounce head on into others as a form of welcome. Initially found somewhat intimidating or annoying by the other members of the Hundred Acre Wood upon his arrival, Pooh and the others eventually warmed up to him and consider him a close friend, especially Roo.
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=== '''Piglet''' ===
 
{{quote| ''Ohhh, d-d-d-d-d-deeeaarr.''}}
 
Extremely timid stuffed piglet. Being someone of such little size makes Piglet rather paranoid and fearful often needing the support of his friends, nevertheless he's very gentle and caring little guy all in all and will face his fears for the sake of others.
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=== '''Eeyore''' ===
 
{{quote| ''Thanks for noticin' me.''}}
 
Stuffed donkey with a deeply cynical and borderline mentally depressed view of life. Often around to share a negative view of things, though is also rather philosophical and can give great wisdom at times.
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* [[Peter Cullen]]: Voice actor from ''[[The New Adventures of Winnie the Pooh]]'' onwards, until Bud Luckey in the 2011 film.
* [[The Stoic]]: Ironically enough. Despite his trademark depressive personality, Eeyore is usually the least likely to become highly fearful or upset in a dire situation, his usual emotional range usually never straying past being somewhat glum and negative. Whatever makes his life is so miserable, he is at least accustomed to it.
{{quote| '''Pooh:''' Are you alright, Eeyore?<br />
'''Eeyore:''' Been better. Been worse too. }}
* [[Surrounded by Idiots]]: Milne's suggested reason for his depressed attitude in the original novels. In the Disney adaptions, he's a much friendlier guy, just ''very'' negative in the most simplistic of terms, though he does have bouts of this trope at times, especially being [[The Chew Toy]].
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=== '''Rabbit''' ===
 
{{quote| ''[[Glad I Thought of It|Splendid idea -- glad I thought of it.]]''}}
 
Grouchy [[Exactly What It Says on the Tin|rabbit]] that is obsessed with getting order and peace in the Hundred Acre Wood. Often finds himself bothered by the antics of the other residents usually Pooh and Tigger, though granted he himself often takes wacky extremes to deal with problems.
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* [[Jerk with a Heart of Gold]]: Often cynical and hostile but will take steps to take care of his friends in the end.
* [[Know-Nothing Know-It-All]]: Perhaps best summed up by Pooh and Piglet in the original novel:
{{quote| "Rabbit's clever," said Pooh thoughtfully.<br />
"Yes," said Piglet, "Rabbit's clever."<br />
"And he has Brain."<br />
"Yes," said Piglet, "Rabbit has Brain."<br />
There was a long silence.<br />
"I suppose," said Pooh, "that that's why he never understands anything." }}
* [[Only Sane Man|Only Sane Rabbit]]: [[Not So Above It All|Though admittedly he himself has rather hair brained ideas at times.]]
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* [[The Smart Guy]]
* [[Super OCD]]: Rabbit is obsessed with order and tidiness and can turn almost any minor fun activity into a highly regimented work routine (usually resulting in a nervous breakdown when the others screw it up).
{{quote| '''Rabbit:''' Have you all gone mad?!? You can't possibly do things...''out of order!''}}
* [[Token Evil Teammate]]: To an extent. He is much more antagonistic than the other residents, however by normal standards, he's just a bit of [[Jerkass]], redeeming himself rather frequently and even plays the [[Straight Man]] on occasion.
* [[Well-Intentioned Extremist]]: Merely wants to maintain order in the Hundred Acre Wood, but resorts to somewhat extreme measures such as kidnapping or traumatizing residents in order to do so (granted however, it hardly ever works).
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=== '''Kanga''' ===
 
{{quote| ''Do be careful, dear!''}}
 
Docile mother kangaroo. Often acts a gentle mother figure to the others.
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* [[Mama Bear]]: Much more gentle than usual examples, but obviously is rather protective of her son.
** The trope is even pointed out by Piglet in the original novel:
{{quote| "There's just one thing," said Piglet, fidgeting a bit. "I was talking to Christopher Robin, and he said that a Kanga was Generally Regarded as One of the Fiercer Animals. I am not frightened of Fierce Animals in the ordinary way, but it is well known that if One of the Fiercer Animals is Deprived of Its Young, it becomes as fierce as ''Two'' of the Fiercer Animals."}}
** This is toned down in the Disney adaptation of their meeting, where Kanga knows full well how harmless the other residents are and ultimately shows mercy on Piglet (with "a cookie and a kiss"), at which point he realises Kanga isn't scary at all.
* [[Positive Discrimination]]: The Disney version arguably. She does at least seem to be the one character lacking a personality-establishing flaw.
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=== '''Roo''' ===
 
{{quote| ''Yes, Mama!''}}
 
Hyperactive joey of Kanga. Shares Tigger's fondness for bouncing and looks up to him like a big brother. Later befriends heffalump Lumpy.
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* [[Tagalong Kid]]
* [[Toxic Friend Influence]]: Tigger plays a light example. While he [[Big Brother Instinct|genuinely tries to look out for Roo]] (and has saved his life at least once) the other residents show awareness that he is [[Cloudcuckoolander|not the]] [[Adult Child|most ideal]] [[Small Name, Big Ego|role model]] for him at times.
{{quote| '''Tigger:''' Taught him everything he knows.<br />
'''Rabbit:''' That explains a lot. }}
 
=== '''Owl''' ===
 
{{quote| ''Good, that will just give me time to tell you about my Uncle Clyde...''}}
 
Scatterbrained elderly owl. Usually shares knowledge and wisdom to the other residents of the Hundred Acre Wood, oblivious to the fact he has as little idea of such aspects as they do. Also likes to share rather frequent (and long) amusing stories about his somewhat eccentric family.
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=== '''Gopher''' ===
 
{{quote| ''I'm *whistle* not in the book, y'know.''}}
 
Full name Samuel J. Gopher, usually littering the Hundred Acre Wood with his endless burrows, often for someone (usually himself) to fall into. Exclusive to the Disney adaptions.
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=== '''Lumpy''' ===
 
{{quote| ''Heffridge Trumpler Brompet Heffalump IV.''}}
 
Roo's new best friend, possibly the only character in the franchise who's younger than him, and one of the elusive Heffalumps -- though unlike previous depictions of these largely unseen monsters he's not the least bit menacing. Another Disney adaptation exclusive, though a much more recent addition than Gopher.
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=== '''Lottie''' ===
 
{{quote| ''Oh, la!''}}
 
A female otter, and the single new character to appear in David Benedictus's ''Return to the Hundred Acre Wood.'' Slightly snobbish and haughty, and so scatterbrained that she makes Tigger look sensible, but ultimately kind and helpful.
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=== '''Kessie''' ===
 
{{quote| ''Rabbee!''}}
 
A baby bird rescued and for a while cared for by Rabbit, whom she calls "Rabbee." A Disney-only character, she appeared only in a couple of episodes of ''[[The New Adventures of Winnie the Pooh]]'', but was brought back as a major recurring character for ''The Book Of Pooh.''
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