Character Analysis
Womp womp
The very definition of Debbie Downer, Eeyore's kind of like a sad clown. You can't help but laugh at him. His episodes usually start with him just sitting still, pondering the black hole of despair that is life in the forest as an old grey donkey. But, y'know, in a funny way.
He can come off as being philosophical and reflective—at one point Milne describes him pondering his own image in the water: "Eeyore, the old grey Donkey, stood by the side of the stream, and looked at himself in the water. / 'Pathetic,' he said. 'That's what it is. Pathetic.'" (Winnie-the-Pooh.6.1-2). But really, Eeyore is an extreme of introspection. He thinks too much about himself—a kind of Kafka figure who's so cynical that he can't accept the good things in life.
When Piglet brings him a present for his birthday, Eeyore has to hear the little guy's intentions three times before he believes it. In this way, he takes on the role of parodying Negative Nancy philosophers. For a grown-up parallel, check out Notes from the Underground.
Of course, Eeyore does have a basis for his complaints. He's left looking for Small until two days after the little bug(ger) was found. He sums that oversight up nicely, too: "'It's just what would happen.'" (House.3.129). It ends up being a kind of self-fulfilling prophecy, but luckily Rabbit pretty much has his number: "'It's your fault, Eeyore. You've never been to see any of us. You just stay here in this one corner of the Forest waiting for the others to come to you. Why don't you go to them sometimes?'" (House.9.21) Rabbit's tough love has an effect on the old grey donkey, who immediately goes out to find a house for Owl. Sure, he finds Piglet's house, but A for effort. That's what we say.