- Eeyore, obviously, from Winnie-the-Pooh. Though he's also The Woobie for his target audience. The original book Eeyore was a very different character from the toned-down Disney version though perhaps more similar to an actual donkey: sarcastic, rude, occasionally arrogant, but also somewhat intelligent.
- 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.
- 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. Puddleglum says at one point that his fellow Marshwiggles consider him to be a hopeless starry-eyed optimist.
- Dolorous Edd from A Song of Ice and Fire pretends to be this way, but he's really just a Deadpan Snarker with this as a shtick and a yen towards Black Comedy.
- Denethor of The Lord of the Rings certainly has real sorrows to contend with — losing his son and watching civilisation 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. 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.
- 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 Brontė'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."