Eeyore!
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Background
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Eeyore is stuffed with sawdust and lives alone, underneath a small, teepee-style house made of sticks. A running gag is that Eeyore's home is almost always knocked over, forcing the gloomy donkey to rebuild it from scratch, usually at a different location. He has his own area in the Hundred Acre Woods known for its dismal atmosphere: "Eeyore's Gloomy Place", where he is typically seen sulking under a rain cloud or eating thistles.
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Apart from his cynical personality, Eeyore's tail is perhaps his most defining trait. Despite being pinned down with a nail, Eeyore's tail frequently detaches from his bottom and winds up getting lost for a period of time. Christopher Robin is typically called upon to reattach it.
Personality
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Eeyore is hardly ever happy, and even when he is, he's still sardonic and a bit cynical. Ironically, he actually seems to enjoy being gloomy to an extent and sees it as the essence of his very being. Nevertheless, he seems genuinely appreciative of the effort his friends put forth to cheer him up and is still a good friend. Eeyore's grumpiness and negative ways might be attributed to the fact that his tail is affixed to his backside using a pushpin and has a tendency to fall off. He doesn't like his tail, but he agrees that nothing better can replace it. He also loves sad stories because they make him feel more appreciative of his life and what he has. He also really likes eating thistles and sugar cubes.
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Even though he complains a lot, Eeyore is generally quite a reliable character; a person you can lean on in times of trouble. He can sometimes be quite insightful, he was the first to understand that the group didn't have to go on a long and dangerous journey to become strong, smart or brave â they had it inside them all along. In addition to this, have shown hints that Eeyore is arguably the smartest, wisest, and most down-to-earth resident of the Hundred Acre Woods and has the most common sense.