1 Eeyore - Winnie the Pooh
Eeyore is a character in the Winnie-the-Pooh books by A. A. Milne. He is generally characterized as a pessimistic, gloomy, depressed, anhedonic, old grey stuffed donkey who is a friend of the title character, Winnie-the-Pooh.
He thinks that he ruins everything for everyone, that's real depressing, I wish I could give Eeyore a big hug. - CasinLetsGoBowling
Did you know that he shares the same voice actor as Optimus Prime? - Pony
His tail always falls off. - EpicJake
Poor him. Never happy. Tail always falls off. How sad. - PizzaGuy
2 Charlie Brown - Peanuts
He's Charlie Brown need I say more
3 Droopy - Tom and Jerry
4 Stainboy - The World of Stainboy
5 Raven - Teen Titans
I don't think she's really sad, she's more of a sarcastic person. - nintendofan126
Yeah, she isn't a person that likes to have fun. - EpicJake
6 Squidward - Spongebob Squarepants
Squidward Tentacles is a fictional character voiced by actor Rodger Bumpass in the American animated television series SpongeBob SquarePants.
In new ones, he's depressed until SpongeBob's diary changes everything. Then he reads it to the Krusty Krab and everyone hates him. he becomes a hobo but he thought it was worth it. In season 6, he entered a deep depression. It stopped in season 9, then he became a jerk. - Goatworlds
He can be sad sometimes, like when SpongeBob is harassing him. I think he is both a grumpy and sad person. - Minecraftcrazy530
I wouldn't say he is sad. He's just grumpy a lot. - cosmo
He's not really sad, he's more of a grumpy kind of person. - nintendofan126
7 Hans Moleman - The Simpsons
Hans Moleman is a recurring character on the animated television series The Simpsons. He was created by series creator Matt Groening and is voiced by Dan Castellaneta, and first appeared in the episode "Principal Charming".
8 Hardy Har-Har - Lippy the Lion and Hardy Har Har
"Oh me, oh my" - the saddest hyena ever! - Billyv
9 Sadness - Inside Out
Must I say more...-Ugh
She is because she's the sad Emotion.
Feel so sorry 4 her
DAH, YOU DON'T SAY
10 Fluttershy - My Little Pony
Fluttershy is a female pegasus pony from the 2010 animated TV show My Little Pony: Friendship is Magic. She is a kind pegasus and is very timid and shy. She takes care of the animals. She represents the element of kindness
11 Kenny McCormick - South Park
Kenneth "Kenny" McCormick is a main character in the animated adult television series South Park, along with his friends Stan Marsh, Kyle Broflovski, and Eric Cartman.
I want to hug my poor lil kenny.
This kid lives in a life of poverty, is physically and emotionally abused by his parents, his so-called friends don't even care about him half the time, and of course, constantly dies and comes back to life. Not only that, but because everyone's memories of his death are erased upon his revival, he has nobody to turn to. He has to deal with his curse alone. - DemonSpider253
12 Ken Ichijouji - Digimon 02
13 Numbuh 1 - Codename: Kids Next Door
The character was sad that Numbuh 1 had to say goodbye to his family and friends in a last episode.
In the episode of "Operation: I.N.T.E.R.V.I.E.W.S where Numbuh 1 sadly says goodbye to his family and friends.
14 Rocko - Rocko's Modern Life
Rocko is the eponymous fictional character of the cartoon Rocko's Modern Life and the comic book series of the same name.
15 Old Gil - The Simpsons
16 Lucy Loud - The Loud House
Lucy Loud is a fictional character in the Nickelodeon cartoon The Loud House. She was created by Chris Savino. Lucy is a goth and likes dark things.
17 Pearl - Steven Universe
Pearl is a fictional character from the 2013 animated series Steven Universe, created by Rebecca Sugar. She is a "Gem", a fictional alien being that exists as a magical gemstone projecting a holographic body. ...read more.
18 Meg Griffin (Family Guy)
Megan "Meg" Griffin is a character from the animated television series Family Guy, voiced initially by Lacey Chabert, thereafter by Mila Kunis.
19 Vicky - The Fairly OddParents
20 Chuckie Finster - Rugrats
21 XJ-7 - My Life as a Teenage Robot
22 Dumbo - Dumbo
23 Cubone - Pokemon
Cubone, known in Japan as Karakara, is a Pokémon species in Nintendo and Game Freak's Pokémon franchise.
24 Casper - Casper the Friendly Ghost
25 Ugly Duckling - The Ugly Duckling
26 Bill Dauterive - King of the Hill
Everything went down after he joined the military.
27 Marvin - The Hitchhiker's Guide to the Galaxy
28 Helga G. Pataki - Hey Arnold!
Even though she can be mean, she’s gotta be one of the most tragic characters Nickelodeon has ever created! #supporthelga!
29 Brian Griffin - Family Guy
Brian H. Griffin, popularly known without his middle initial as Brian Griffin, is a fictional character from the animated television series Family Guy.
Yeah Brian died after he got hit by a car that Stewie destroyed the time machine in a tearjerking episode.
30 Mufasa - Lion King
Mufasa is a major character in Disney's 1994 animated feature film, The Lion King. He is Simba's father, Sarabi's mate, Scar's older brother, and was King of the Pride Lands until his death.
31 Seymour Asses - Futurama
32 Mona Simpson - The Simpsons
33 Atlas - Astro Boy (2003)
34 Enzo Matrix - ReBoot
35 Dinobot - Beast Wars: Transformers
36 Goku - Dragon Ball
Son Goku (Kakarrot) is the main protagonist in Dragon Ball franchise created by Akira Toriyama in 1984. He has many abilities like, super strength, utilization of ki, flight, teleportation, super speed, enhanced reflexes, and Super Saiyan transformation that increase strength, speed, and durability. ...read more.
37 Cosmo - Sonic X
38 Pops - Regular Show
39 Ash Ketchum - Pokémon
Ash Ketchum, known as Satoshi in Japan, is a fictional character in the Pokémon franchise owned by Nintendo. Ash is training to be a Pokemon Master, with his buddy Pikachu. Ash tries to stop the evil Team Rocket from stealing his Pikachu.