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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.
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.
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.
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 ― 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 narrator 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 is believed to have 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 he's smarter than he thinks and Tigger realizing he's stronger than he seems and Piglet realizing he's braver than he believes. 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 actually at school, as Owl was incorrect in his deciphering), and return home.
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 creates 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 usual 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 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 honeypot, Pooh is rewarded a massive jar of honey.
In the live-action film, Eeyore, Pooh and the other animals of the Hundred Acre Wood join Christopher Robin in saying goodbye to him when he prepares to leave for boarding school.
Years later, when Pooh's friends all go missing, he asks Christopher Robin to help him find them. After getting separated from Pooh, Eeyore is the first of the group he manages to locate, with Eeyore having fallen into the stream. Though Eeyore is rescued, he doesn't recognize the adult Christopher Robin and believes him to be a heffalump. However, he accompanies Christopher Robin in finding Owl, Kanga, Roo, Rabbit, Tigger, and Piglet who is likewise convinced that Christopher Robin is a heffalump. To regain their trust, Christopher Robin takes Eeyore and runs behind a stand of trees and pretends to vanquish a heffalump. Eeyore then quickly and happily realizes that he is with Christopher Robin and helps further the illusion by making heffalump sounds. As a result of their trick, Christopher Robin regains the trust of the animals of the Hundred Acre Wood. He also helps in finding Winnie the Pooh afterward.
When Christopher Robin leaves and Tigger inadvertently removes Christopher's important paperwork, Eeyore accompanies Pooh, Piglet, and Tigger to return them. In doing so, they end up meeting Christopher Robin's daughter, Madeline Robin and rush with her to London to help return her father's paperwork to him at his job at Winslow Luggages and to dissuade him from sending her to boarding school. During this time, they also teach Madeline what it means to have fun. During the journey, they manage to stow away in the back of one of the company's supplies trucks. However, he, Tigger and Piglet are separated from Madeline and inadvertently are reunited with Christopher Robin, where they meet his astonished wife, Evelyn as well. Upon reuniting with Madeline, Eeyore, Pooh, Piglet, and Tigger are present with Christopher's family to hear him speak about his plan involving reducing the prices of luggage, giving employees paid leave, and selling their luggage to everyday people to increase demand so that Winslow's employees can keep their jobs. When Giles Winslow Jr. scoffs at this plan and is humiliated because of everyone else including his father (Winslow Sr.) warming to this plan, Eeyore eyes him with a look of satisfaction at Giles' comeuppance, causing Winslow Jr. to wonder in bewilderment if he's actually seeing Eeyore staring at him. When Christopher Robin brings his family to the Hundred Acre Wood to meet the rest of the other animals, Eeyore celebrates and picnics with them.
In a mid-credits scene, Eeyore, Pooh, Piglet, and Tigger are seen relaxing at the beach with the employees of Winslow Luggage and Christopher Robin’s neighbor.
Brad Garrett returns to voice Eeyore, whose design resembles both E.H. Shepard's illustrations (removing the pink bow on his tail) and the Disney iteration (with his bulbous snout).
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 trail 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 times and reasons.
Eeyore was portrayed by a puppet in the series and was the focus of various episodes, such as "My Gloomy Valentine", where Valentin's Day has arrived and everyone's received a valentine except for Eeyore, much to his disappointment. Another notable episode is "The Case of the Disappeared Donkey", where Eeyore goes missing, prompting Tigger to embark on a search for him. Perhaps Eeyore's most significant role was in "The Book of Boo" where Eeyore, not understanding the fuss of Halloween, claims that he doesn't find the gang's Halloween tricks to be scary. By the end of the episode, Piglet accidentally scares Eeyore, which in turn, puts him into the spirit of the season.
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 the computer-animated series, Eeyore appeared as a supporting character, mostly in bits and pieces throughout the episodes. Like the other Hundred Acre Woods inhabitants (sans Pooh and Tigger), Eeyore would sometimes call upon the Super Sleuths to solve a problem, though he tends to be reluctant in doing so. In "Eeyore Sleeps on It", the sleuths learn that Eeyore has a problem with sleepwalking. In "Eeyore's Dark Cloud", Eeyore's depression manifests into a literal dark cloud hovering above him, which eventually disappears, resulting in Eeyore calling the sleuths go get it back. When not the focus of a problem, Eeyore would sometimes join the Super Sleuths on an adventure.
Eeyore makes a guest appearance in the special episode "Into the Hundred Acre Wood". When Pooh goes missing, Eeyore joins Tigger and Piglet in trying to find him. During their search, they run into Doc McStuffins and her group of anthropomorphic stuffed animals. She intrudes herself as a doctor for toys, which Eeyore is astonished by. He also becomes acquainted with Doc's snowman plush, Chilly.
In Kingdom Hearts II, Heartless tore out pages from the 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 third most common character from the Pooh franchise (after Pooh and Tigger). Like Pluto, Eeyore walks on his hind legs at the parks although he did walk on all fours in Welcome to Pooh Corner and Disney Live! like in the cartoons.
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.
Eeyore is the only one of the toy animals to have more detailed eyes as opposed to just having black doted-eyes, while Rabbit and Owl also have detailed eyes they were both real animals as opposed to toy ones.
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 on the British Cockney dialect version of the phrase "hee-haw".
Eeyore is the current reigning champion at Poohsticks.
In Christopher Robin, Eeyore has a silly habit of calling Evelyn Robin "Evelyn My-Wife" as he believes it is her full name.
Eeyore constantly losing his tail and needing it pinned to him could be a reference to the party game "Pin The Tail On The Donkey".