Eeyore is a fictional character from the book series and cartoon Winnie the Pooh. Eeyore spells his name "eoR". He is a pessimistic, gloomy, old donkey who happens to be a friend of Winnie the Pooh. Eeyore is hardly ever happy and when he is he's still sardonic and a bit cynical. His grumpiness might be attributed to the fact that his tail is affixed to his behind using a pushpin. Nevertheless, he seems genuinely appreciative of the efforts of his friends to cheer him up, for example, when Pooh and Piglet build The House at Pooh Corner for him, or when they give him birthday presents of a honey jar (empty) and a balloon (accidentally burst).

Eeyore is always overlooked and is often used as a beast of burden, most notably when he was ridden by Rabbit in his search for train "borowers" in The Tigger Without a Name and The Pooh with a Name. Nearly all of Eeyore's houses have fallen down, been knocked down, or been bounced down. However, Eeyore is not good at building the houses; butterflies often knock them down just by landing on them. Yet, like tortured Sisyphus, he soldiers on and rebuilds again, time after time.

Despite his depressive nature, Eeyore is capable of great compassion, which is shown when he grows a plant that Rabbit (a master gardener) was unable to grow, just by showing the plant a little love.

In merchandise by The Walt Disney Company, Eeyore always has an uncharacteristic smile. Also, he is somewhat less caustic and sarcastic in the Disney version than in A. A. Milne's original stories. It must also be noted that Eeyore's tail was not always fixed to him by a pushpin, although Disney has chosen this as part of his permanent image.