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Perhaps another way to go at this is to ask the question this way: Everyone in the Pooh books has lessons to teach, or has had lessons assigned to them (Benjamin Hoff wrote two books about such lessoning, The Tao of Pooh and The Te of Piglet. What lessons does Eeyore have to offer?
Let's start with Hoff's rendition of Eeyore – call it the usual picture of the grey donkey. He calls it The Eeyore Effect (in the chapter of the same name in his The Te of Piglet). Here is his central description of the Effect (all the capitalized words are original) — it is Hoff in a huff:
Eeyores, in other words, are Whiners. They believe the negative but not the positive and are so obsessed with What's Wrong that the Good Things in Life pass them by unnoticed. Are they the ones, then, to give us an accurate account of what life is about? If the universe were governed by the Eeyore Attitude, the whole thing would have collapsed ages ago. Everything in creation, from migrating hummingbirds to spinning planets, operates on the belief that It Can Be Done....Therefore, no society that wants to last is going to be guided by Eeyores. For Eeyores sneer at the very things that are needed most for survival and prosperity. (59-60)
Well.
Hoff goes on to associate Eeyore and his supposed Attitude with negative-reporting media, the Puritans, Critics (yes, the capitalized ones), a horrible education system (the Education Eeyores), and, weirdly enough, people he calls the Eeyore Amazons, hyper-feminists who perversely act from a hyper-masculinity rather than from a true femininity.
In Hoff's bipolarish world of the East and West, of the natural vs. the inorganic, Norman Vincent Peale vs. Arthur Schopenhauer, the lessons that Eeyore offers are not worth learning because, in his view, all Eeyore ever does is "make others feel small, especially if they're smaller than he is [which] makes him look big..." (53) Eeyore is a passive-aggressive bully, a buzz-kill, a Tao damper. He acts how we shouldn't.
Is this the reason, then, Milne includes him in the Pooh menagerie? A taste of the chili pepper to cut the saccharine?
Not exactly, I don't think, because Milne has him behave in ways that are not just counter or contrary to the other residents, or as a commentary upon their actions. Eeyore's actions are more complicated than that, in part because, except for Christopher Robin, he's the only one who goes through any changes in his behavior.
Eeyore is the only character that Milne gives fullness to because he is unsettled, unsettling, contrary, polite but not obsequious, snarly in his humility, purposefully cranky, intelligent, unillusioned. Everyone else in the Wood is somewhat monotone, which makes them easier to "love" (as many generations have): Pooh's artful cluelessness masking as innocence, Piglet's perpetual timorousness, Tigger's goofiness, Kanga and Roo's mother/son act, Owl's predictable wrong-headedness – like characters in a sitcom, they retain an unconfusing personality resistant to change. Never will Pooh turn to the others and say, "My life feels suddenly very empty – and honey will do nothing to change that feeling."
With Eeyore, on the other hand, Milne presents his readers with a challenge, a specifically Christian challenge. It is easy to love the loveable characters – anyone can practice Christian charity with someone who doesn't talk back and requires no sweat-equity.
Eeyore is the prickly character that requires one to be a real Christian because he is not willing to play the game. To love Eeyore means working to gain his respect, since he won't give it to you without you making the effort to win it. To love Eeyore means accepting him as he is and foregoing any impulse to change or "improve" him. To love Eeyore means accepting the possibility that he will not love you back – no quid for the quo.
And all of this is complicated by Eeyore's capacity for charity and compassion, though he does not wear his heart upon his sleeve.
Take the last chapter of Pooh Corner, when Christopher Robin is going away and Rabbit has asked Eeyore to compose a "rissolution" about this sad situation. His attitude in reading the poem out loud to the others and then presenting it to Christopher Robin unread is a bluster that masks his sadness at Christopher's leave-taking (since Christopher Robin is the only one he considers his equal). Notice how beautifully Milne captures the way an aching heart ties our tongue at the very moment when we wish we could be perfectly articulate:
"Christopher Robin," he said, "we've come to say – to give you – it's called – written by – but we've all – because we've heard, I mean we all know – well, you see, it's – we – you – well, that, to put it as shortly as possible, it is what it is." He turned round angrily on the others and said, "Everyone crowds round so in this Forest. There's no Space. I never saw a more Spreading lot of animals in my life, and all in the wrong places. Can't you see that Christopher Robin wants to be alone? I'm going." And he humped off.
Not quite knowing why, the others began edging away, and when Christopher Robin had finished reading POEM, and was looking up to say, "Thank you," only Pooh was left.
It's no coincidence that Eeyore's food is the thistle, with both its nettles and beautiful blossom.
Eeyore's life is not easy because he is making an effort to be actual and consequent rather than give in to what he would consider the easier ways of conformity or faith.
It is also a life not sufficiently nutritious, for it needs some Pooh and Tigger for leavening – even Eeyore, at various times in the books, experiences joy, and part of him is always pleased when someone seeks him out, even if he is distrustful of the impulse that brings visitors to his doorstep.
The core of Milne's Eeyore is a hybrid of the strong wish that he, too, could have Pooh's charmed, angels-watching-over-him kind of life butting up against what he sees around him: venality, insincerity, entropy. It is the Christian dilemma: the ache to return to the unobligated life in Eden is grafted onto a body fated to die and a mind that can never forget this.
Eeyore always castigates his fellows for not thinking enough, for not seeing things as they are, but this is in part an expression of Eeyore's own desire for life to stop being thistles and more like honey. His "gloominess," if that is the right word, is his recognition of the wrongness of Hamlet's declaration that "There's nothing either good or bad/but thinking makes it so." We can think whatever we want, but, as Hamlet finds out, and Eeyore knows, there is only so far we can go in fooling ourselves – reality always demands that we notice it and honor it – what is sarcasm and irony but two ways to do this?
And, as Hamlet says, once we are infected with consciousness, there is no going back to Eden except in ways that are, in some sense, fraudulent: yoga, meditation, Christianized good works, and so on. All efforts to forget, and by forgetting cleanse the virus.
And yet, without the practice of those fraudulences, much goodness and light in the world passes us by and does not get done, because out of them flows compassion and charity. And even Eeyore would concede that at times it feels good to forget, to let the sarcastic and ironic slip away, to just "do" without reasoning why.
As the writer Spider Robinson said, back in 1977, "If a person who indulges in gluttony is a glutton, and a person who commits a felony is a felon, then God is an iron." The whole moral universe of human life seems based on this. Even if one is an atheist, something out there seems to bend all of human life toward irony and jokiness.
So I think the characterizing of me as an Eeyore is not quite right – that is, the common Eeyore, Piglet's gloomy one. Yes, there is that about me, but not just that. I am also one with thistles, who will be polite and courteous but is also rageful underneath, who distrusts learning's ability to teach us anything yet who never stops hungering to learn, who always thinks life gives us less than what it promises, that sentimentality is both comforting and untruthful, that life is dry rather than moist, cool rather than warm – that we are all fragile blusters of pain always on the cusp of annihilation who mythmake to soften this condition and gain some respite (because who can live for any length of time on the cusp? but that is where all good art gets made, so someone needs to live there).
If what I've said about Eeyore is right, then I'm glad to be Eeyore.
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