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.
Eeyore is generally quite a reliable character; a person you can lean on in times of trouble. He can sometimes be quite insightful -- in Winnie the Pooh's Most Grand Adventure, 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 -- they had it inside them all along. In addition to this, a few episodes of the animated series The New Adventures of Winnie the Pooh 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 (along with Kanga), most notably seen in the episode "Stripes" and "Home is Where the Home is".
Eeyore is featured as a minor character in two of the three segments. In Winnie the Pooh and the Honey Tree, he is introduced by the narrators as being "stuffed with sawdust". He had lost his tail, and it was being fixed by Christopher Robin. Eeyore later assists in pulling Pooh out of Rabbit's doorway (by taking hold of Kanga's jumping tail).
In Winnie the Pooh and the Blustery Day, Eeyore tasks himself with finding Owl a new home, after Owl's had been blown down by the wind. He sticks to his task, even while the woods are flooded. Eeyore eventually finds a house for Owl, mistakenly choosing Piglet's house for Owl. Even though Pooh encourages Piglet to point out the mistake, Piglet generously offers his home to Owl.
Eeyore is first seen floating in the river, while Pooh is playing a game of Poohsticks. A flashback, courtesy of the Narrator, reveals that he had been deliberately bounced by Tigger. Pooh notices that Eeyore is more depressed than usual, and asks Eeyore what's wrong. Eeyore reveals that it's his birthday and no one has noticed.
Later, Pooh reappears with an empty honey pot (he had eaten the honey along the way), alongside Piglet who had intended to bring a balloon, even though it had popped. Despite this, Eeyore is touched by the gifts, because he can place the balloon in the pot and take it back out. Eeyore later attends a birthday party in his honor, put together by Christopher Robin. Tigger later appears uninvited, despite Rabbit's protests regarding Tigger's previous treatment of Eeyore. Christopher Robin decides to take everyone to the river, where they play Poohsticks. Eeyore, who is playing for the first time, is revealed to be a natural, and wins most of the games, while Tigger wins none. Eeyore later shares his secret with Tigger.
Eeyore joins in the hunt for Christopher Robin, who has gone missing. Owl misread Christopher Robin's note, causing everyone to go on an adventure to save him from "Skull." In the film, Eeyore is the only character that goes on the journey and doesn't accomplish anything, such as Rabbit realizing that he's smarter than he thinks and Tigger realizing he's stronger than he thinks. Despite this, Eeyore was the first to realize all the friends had their special ability in themselves all the time. They find Christopher Robin who was really gone at school and Owl was only joking. He is the only member of the gang who doesn't have a character arc.
Once again poor Eeyore's house is destroyed and this time by a huge boulder. Eeyore's faithful friends create a pulley system with the guidance of Rabbit to remove the boulder but the plan goes into hot water after Tigger uses a special bounce to move it. All the ropes tangled the gang and Eeyore along with the device which goes twirling down a hill and into a pond. Eeyore shows he's even more upset about the whole incident.
Pooh Bear believes Tigger deserves a real family and Eeyore helps Pooh search for them. Little Roo gets the idea to make a letter to Tigger and all the friends place their own saying while Eeyore's is "Keep smiling."
Eeyore is shocked to see Tigger thinking the letter was from his actual family. Eeyore and his friends create Tigger costumes. At first, Eeyore was unexcited but eventually started to smile and find it amusing. Tigger notices the Tiggers are actually his friends in costumes and shocked to see Eeyore was a part of it. The gang search through a blizzard to find their friend including Eeyore and the all reunite. As a thank you gift, Tigger creates a beautiful home for Eeyore.
Eeyore is first seen in the film's opening as a part of Pooh's master plan of getting honey from the bees. Eeyore's job is to lure the bees to the decoy hive held by Pooh and Tigger. The plan is a disaster until Piglet saves the day. No one (including Eeyore) noticed and celebrated without Piglet. When the bees free themselves from the fake hive, they chase Eeyore and the gang. Eeyore is left outside while Pooh, Rabbit, and Tigger reach Piglet's home safely. Eeyore returns and was stung.
Rabbit notices Piglet's absence and they search for him. They use Piglet's scrapbook as a map and when taken away by a river, the group create their own scrapbook to Piglet's dedication and return to find him. The original book was found at the edge of a log over a waterfall and Pooh risks his life to recover it. Eeyore helps the group make a rescue rope, but they're not long enough. Piglet arrives and saves Pooh in the nick of time. Eeyore joins the celebration honoring Piglet.
Eeyore reappears in the film and joins the group led by Rabbit in the first-ever Heffalump expedition. During the movie, Eeyore is accidentally separated from the group, but reunites with them during the end credits and meets the new group member, a Heffalump named Lumpy.
Eeyore is first seen being more gloomy than usually at his home. Pooh pays a visit in a search for honey but instead finds out that Eeyore has lost his tail again. Pooh and Eeyore are then greeted by Owl who flies over to Christopher Robin for a solution to the problem. Christopher sets up a contest for the recovery of the tail or a substitute, with honey as the reward. Pooh uses a cuckoo clock, but as Eeyore took a seat, it was destroyed. Piglet used a balloon but it floated Eeyore into the air. Next, Kanga knitted a replacement tail, but it unraveled.
After a while, Eeyore went over to Owl's house where Owl provided a chalkboard as a tail and incorrectly labeled it "Tael". Just then, Pooh arrived and asked Owl to decipher a note he found on Christopher Robin's door. Owl reads the note as if it were a distress note, informing the friends that Christopher has been captured by a creature called the Backson. A search for Christopher begins but Eeyore is left behind because he couldn't keep up. He runs into to Tigger who proclaims Eeyore "Tigger Two", feeling remorse for his lonely friend. After some comical Tigger training, Eeyore decides to leave the scene and hides in a pond until Tigger leaves.
At the bottom of the pond, Eeyore finds an anchor for a tail and heads over to Rabbit, Kanga, Roo, Owl, and Piglet as they try to get Pooh out of a pit trap meant for the Backson. Rabbit decides to use the chain of Eeyore's anchor to get Pooh out, but the anchor pulls Eeyore into the pit with Pooh and drags everyone else along too. Eventually, Tigger and Piglet are trapped as well and Eeyore no feels that he and his friends will soon perish stating "We're all gonna die." However, Pooh creates a ladder using the textbook letters. The gang is freed and Christopher Robin appears explaining that he was only at school. That evening, Pooh finds Eeyore's real tail at Owl's house, being used as a bell ringer. Pooh returns it and Christopher places it back on. As a reward for choosing to return Eeyore's tail before getting a honey pot, Pooh is rewarded a massive jar of honey.
Eeyore appears as a main character in the series and has several episodes regarding him. In "Donkey for a Day," everyone mistakenly thinks Eeyore is depressed when they see him sitting alone on a cliff. They try to cheer him up through various activities. Later, Piglet goes to talk to him, and Eeyore says that he wasn't sad at all. Instead, he comes to the cliff when he is happy, and he shows Piglet a game he plays with the clouds.
In "The "New" Eeyore," Eeyore decides that he would like to become more popular. Seeking advice, he speaks with Tigger, who advises him to smile and say hello. Later on, Eeyore misinterprets Tigger's final piece of advice (Tigger mentioned that people liked him because he acted like himself) and decides to begin acting and looking like Tigger. Eeyore is later corrected by his friends and decides to be himself, though he retains the lessons of smiling more and saying hello to others.
"Eeyore's Tail Tale" shows Eeyore becoming sick of his tail and leaving it behind. He later regrets this and decides to regain it, but not before the tail makes its way to each of his friends, who each use it for a different purpose. Meanwhile, when each friend loses the tail, Tigger decides to solve the crimes. When the tail is finally found, Eeyore is able to reclaim his tail from his friends, who had been unaware of its true purpose.
A running gag through the show is that Eeyore's house (which is made of sticks) is knocked over for various reasons.
Eeyore has made numerous cameos in the show, usually seated with other characters from the Winnie the Pooh series. His most notable appearance was in "Unplugged Club," in which he made a special appearance at the club as a stand-up comedian. In "Dining Goofy," he showed to be not amused by the fact that he was seated with Jiminy Cricket. In "House of Turkey", he commented on the show's behind-the-scenes plot revolving several guests trying to devour the Guest of Honor, who happened to be a turkey.
Eeyore also makes a notable appearance in Mickey's Magical Christmas: Snowed in at the House of Mouse, where he goes on stage and tells the guest what he's thankful for. Eeyore states that he's thankful for laughter, joy, and the high-spirited glee that "fills my heart to overflowing," and then sighs. This segment was recycled in "House of Turkey".
In Kingdom Hearts, Eeyore appears after Sora had already met Pooh, Tigger, Roo, Piglet, Owl and Rabbit. The group recovered Eeyore's lost, strap-on tail. A version of him is created out of Sora's memories, in Chain of Memories. In Kingdom Hearts II, Heartless tore out pages from Hundred Acre Wood's book, giving Pooh amnesia. Eeyore appeared later in the world and Pooh remembered his name, after being fed honey to trigger his memory.
In the Disney theme parks around the world, Eeyore is a fairly common character; the thir most common character from the Pooh franchise (after Pooh and Tigger). Like Pluto, Eeyore walks on his hind legs at the parks rather than walking on all four legs like in the cartoons.
While Eeyore is gray in animation and puppetry, he is blue in merchandise.
Nearly all of Eeyore's houses have fallen down, been knocked down, or been bounced down. Eeyore is not very good at rebuilding 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.
Eeyore's birthday was December 25, 1921, when Christopher Robin got him as a Christmas present.
Despite his depressive nature, Eeyore is capable of great compassion and empathy, 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 and cover art, 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 wasn't always fixed to him by a pushpin, although Disney has chosen this as part of his permanent image.
Age wise, Eeyore may be the oldest member of the group.
Eeyore’s name is based off the British Cockney dialect version of the phrase “hee-haw”.