The Eeyore / Literature

• Winnie the Pooh: Eeyore is the Trope Namer and The Woobie for his target audience. The original book Eeyore is more of The Killjoy sarcastic, rude, occasionally arrogant, but also somewhat intelligent; which maybe is more akin to an actual donkey. Disneyfication toned that down, however.
• Dax from Greystone Valley. He seems to be afraid to be happy.
• Gil Peaply from Felsic Current falls under just about every trope that involves depression, cynicism, jadedness, whining and sarcasm, but The Eeyore is perhaps the best match for him.
• A Series of Unfortunate Events: The Lemony Narrator Lemony Snicket, who would much rather be doing something else - like enjoy the sun or the grass or actual conversation - than follow three miserable children in a miserable, unfortunate story.
• Melinda Sordino from Speak. While part of it is natural angst of trying to find one's place in the world as a teenager, Melinda is unusually morose even by that standard. This is because she was raped by the resident Jerk Jock, and no one seems to believe her.
• Ann from the Gemma Doyle trilogy.
• Puddleglum the Marshwiggle from C. S. Lewis's Narnia book The Silver Chair—referenced in More than Mind Control. Dialogue from other characters indicates that this is the Marshwiggle's hat. Puddleglum says at one point that his fellow Marshwiggles consider him to be a hopeless starry-eyed optimist. Whether that's true or just him still being an Eeyore is left to the reader to decide.
• Dolorous Edd from A Song of Ice and Fire certainly presents himself this way, but he's either a Deadpan Snarker with this as a shtick and a massive lean towards Black Comedy or the Eeyore-ist Sad Clown trying to cope through deflection and humour with living in a world chock-full with a range of thoroughly mundane, highly visceral, blatantly Kafkaesque and subtlety Lovecraftian horrors. It's hard to be certain which is the case. Or if both.
• Denethor of The Lord of the Rings certainly has real sorrows to contend with — losing his son and watching civilization apparently crumble around him. But he's definitely a fatalistic old bugger on top of it, thanks to repeatedly using a palantír and getting into mental fights with Sauron, and operating under the false belief that Sauron already has the ring back (which really would make things hopeless). In both the book and the film he sums up his attitude towards humanity's future in the splendidly morose line: "Go now and die in what way seems best to you."
• Marvin the Paranoid Android from The Hitchhiker's Guide to the Galaxy is perhaps the Eeyore-iest Eeyore in existence. He's very depressed, he feels under-utilized ("Here I am, brain the size of a planet, and..."), and due to a series of circumstances involving time travel he eventually gets to be thirty-seven times as old as the universe itself and throughout his entire existence he's had this terrible pain in all the diodes down his left side. His outlook on the universe is so depressing that he drives a computer to suicide when he tries to share it with the poor thing. He later does the same thing with a bridge.
  Marvin: Where's the percentage in trying to please a robot that doesn't have any pleasure circuits?
  Receptionist: And you don't?
  Marvin: I don't know. I've never had any occasion to find out.
• The Crew of the Copper-Colored Cupids has Pessimist-242, who combines this with The Cynic. Like Marvin, he's actually enormously competent and effective when other characters manage to needle him into taking on a given mission, but he lacks the motivation to put his talents to any uses other than sitting around, wallowing, unless specifically directed.
  "He was on vacation at the moment, which suited him, as he always felt rather vacant. And since he assumed that trying to enjoy his vacation and take some time to rest would surely go wrong, he wasn’t even trying."

  — Magic Trick
• Worvil in Jennifer Trafton's novel The Rise and Fall of Mount Majestic. At one point, "Worvil's upside-down stomach turned inside out, split into a dozen pieces, and started a civil war."
• Billy Jack, Dusty's sergeant major in the Civil War novels of J.T. Edson. He believes every mission is doomed before it starts. A sample of his dialogue from Under the Stars and Bars:
  "Damned if I wasn't certain sure we'd all get blowed up, being so close," Billy Jack wailed and, in expression of his delight, continued, "I dropped on to a rock 'n' must've caved my ribs in. Likely I'll be dead from my hurts come morning."
• Mundo Cani Dog in The Book of the Dun Cow is permanently depressed and self-hating, accepting and agreeing with any insults. He only laughs once in the entire book.
• Mrs. Yorke from Charlotte Brontë's Shirley is one, and considers it morally wrong to be anything else. Unfortunately, she has six children whom she is trying to convince to be as miserable as she is.
• In Those That Wake, Mike is this due to feeling worthless.
• The Catcher in the Rye: Holden Caulfield of course, to the point he seems to associate any positive emotions with "phoniness."
• The Earthworm from James and the Giant Peach. The Ladybug puts it best: "He loves to make everything into a disaster. He hates to be happy. He is only happy when he is gloomy."
• Temeraire: Mr. O'Dea is a valuable and trusted member of Laurence's Dragon Riding team for the latter half of the series, but always expects the worst to happen and has a tendency to wax lyrical about his dire predictions that even Laurence finds tiresome.
• A Man Called Ove: The title character, Ove, borders on this. He's a jaded 59-year-old man who is down in the dumps after losing his beloved wife Sonja. Due to being overwhelmed with grief over Sonja's death, Ove has even attempted suicide. However, his personality may alternate between this and a Grumpy Old Man, much like the Trope Namer.
• Pindakaas en Sushi: Esther, who doesn't seem to remotely enjoy talking to other people and appears to be sulking most of the time. Then it becomes a Zig-Zagged Trope when the next day she is quite happy, to Marle's surprise. The reason being that a band she absolutely loves is giving a concert that day. However, she reverts to her negative personality later on.

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