Depressed cartoon characters?

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Strong Sad

I don't know if Eeyore technically is depressed as he is just really gloomy. There was this one cartoon episode in "The New Adventures of Winnie-the-Pooh", where his friends are concerned because he keeps staring up at big grey clouds. They keep trying different ways to cheer him up but it doesn't work, until finally Piglet sits down and talks with him and realizes Eeyore isn't staring up at the clouds because he's sad, he's really playing a game where he looks for shapes in the clouds and soon Piglet and his other friends join him.

This was back when "The Complainer Is Always Wrong" message was still pretty common in kid's cartoons, so it was pretty refreshing, actually.

Himura Kenshin from Rurouni Kenshin. I think especially in the OVA series.

Sadness

There was this really good recent anime called March Comes in Like a Lion, which did a great job at getting you into the head of someone who has depression, the struggles from the highs and lows (feeling unworthy of the highs), and how it grips the person in a feeling of sinking. The main character, Rei Kiriyama, being the most overt example of a person with depression. An anime/cartoon so much about depression sounds like it would be.... well, pretty depressing, but I think that there is something to it in the feeling not alone in something, and is a good watch to feel through something similar.

There was this song and music video called "Fighter" that was made when it was a manga by a band called Bump of Chicken, which got a seal of approval from the creator, and then was taken on board for songs when it was turned into an anime, and became a big part of general tone for it. I will link the music video because I think that it is a great job at showing the struggles of the character with depression, and recommend to check out if you are interested (the actual anime looks better).

Sailor Venus probably has Bipolar Disorder I think

Pinkamina Diane Pie

This guy...

Bill from King of the Hill

Hercules after he lost his powers

Squidward Tentacles from SpongeBob SquarePants

Eeyore from Winnie the Pooh

Does Donald Duck count as depressed?

Charlie Brown

Eeyore

Dumbo

Riley - Inside Out

Me.
Also, Marge Simpson. She has suffering in her eyes.

Moe from The Simpsons. Possibly Barney from The Simpsons, too.