Top 10 Saddest Cartoon Characters of All-Time

A typically sad moment

When we think of cartoons, we tend to think of joyful animals prancing in a sunny meadow or a modern American family trying to get along without too many arguments or flashbacks. But there’s a dark underbelly to the comic and cartoon world and that underbelly is called sadness.

As shocking as it my seem, there are indeed sad cartoon characters – more than you might think. Here’s 10 of the most miserable, misunderstood characters who all share one thing in common; the longing for the sweet release of death.

10. Lamington

He might not be as well known as some of the names on the list, but believe me, he’s just as damaged. Lamington is a Boston Terrier puppy who lacks the ability to feel joy of any kind, and just wants to be left alone with a migraine. He loves rainy days, silence, cold tea… kind of like Morrissey, but cuter and less racist.

His friends, being the modern sociopaths that they are, want to cheer him up by any means necessary. Which is kind of a metaphor for society in general. In today’s world, it is not OK to be sad. For example, you can’t turn up to your dead end job in a shitty mood and curse everyone out, even though that is the correct response to the situation. No, everyone must be happy all the time. It’s a facade and Lamington is the poster boy for emotional honesty.


9. Grumpy Bear

The Care Bears were generally considered a fun bunch, zooming around Care-A-Lot in their cloud cars and drinking milkshakes laced with smiles, but one of their species broke all the Care Bear rules. That maverick was Grumpy Bear, a miserable sack of blue shit. Sporting a cloud on his tummy to indicate the inner rage that bubbled under his furry surface, Grumpy Bear was ready to throw down at a moment’s notice. Forget to include him in your plans to paint a rainbow? A week’s silence. Tell him to get over himself? Violent outburst of profanity (I’m guessing). He was essentially a very unstable personality with no right to call himself a Care Bear, and yet without his acerbic personality, Care-A-Lot would be the most saccharine, insufferable place in the world. You could say he brought balance to the force (of caring).


8. Stainboy

We all know Tim Burton from his wonderful version of Planet of the Apes, but before that (if you can believe it) he was a creative artist with vision and a style all his own. He even worked at Disney for a while as an animator before going on the become a director of Johnny Depp in white-faced make up. Jump to the year 2000 and the invention of the ‘internet cartoon’. Tim Burton’s Stainboy was a series of shorts starring the eponymous hero as a sort of detective who rounded up other freaks such as Stare Girl and Toxic Boy. Stainboy himself was a melancholy fellow who never spoke, just experienced the drab watercolor world he lived in without comment. Pretty sad.


7. Roast Beef

A cat from the comic strip Achewood, Roast Beef himself admits he’s “got depression”, Seasonal Affective Disorder and Avoidant Personality Disorder. Like most sad cartoons, he had a rough childhood (once overhearing his mother killing his dad) and was therefore raised by his abusive Grandma in a trailer. Now he lives in his best friend’s shed, programs code (all coders are depressed, they just don’t know it) and blogs about how awful the world is. Even though he can’t ‘speak’ with capital letters or punctuation, Roast Beef makes some eloquent points and knows what he likes: total isolation. This guy has problems.


6. Fiver

Aww, a cute rabbit! He’s so fluffy-OH MY GOD HE’S HAVING BLOOD-SOAKED NIGHTMARISH VISIONS OF THE FUTURE! If you’ve ever seen Watership Down, and I pity you if you have, you’ll know that a rabbit’s life is not a happy one. No hopping around the first blooms of Spring and munching on crisp carrots for these bunnies. Uh uh. That would be too non-terrifying.

Fiver has it especially bad, with his ability to see the coming deaths of his friends in vivid gory detail. Naturally, if you saw crushed bones and tearing flesh every time you closed your eyes, you’d be a little upset yourself. Fiver is basically on the brink of a massive nervous breakdown, and that really has a knock-on effect on his happiness.

5. Droopy

Let’s get this out there: Droopy is a pimp. He’s always packing heat and has a taste for curvy girls who work in nightclubs. He loves that ass.

Unfortunately, he has no emotions. The guy never smiles. Never laughs. He could crush your head in a vice without even blinking. He is dead inside and merely going through the motions of this pathetic merry-go-round we call life. Droopy knows what you don’t let in, can’t hurt you. In this case, “it” is a large wolf with a giant hammer, but the point remains.

4. Carl Fredricksen

Carl is the lead character from Up by Pixar. Before this movie was released the internet was abuzz with chatter. “Who wants to watch a cartoon about an old fart?” critics and fans asked. Turns out the answer was “People who love to cry in the dark” and luckily for Pixar, there’s millions of us. Carl was a happily married man for many years, until he lost… something (no spoilers), and then he turned into a shell of utter sadness, with a healthy twist of bitter. The last straw was having his home taken away by evil re-developers, so Carl does what any of us would do and floats his house away to a land of talking dogs. And he’s still not happy! Eventually, he does beat his rival (another old guy) and returns home a changed man, but really, how many years does he have left? One? Better not to think about that.

3. Eeyore

This sorry bastard is the donkey from Winnie the Pooh. Despite living in the beautiful untouched English countryside, Eeyore is clinically depressed to a serious extent. He should probably be on suicide watch before they find him hanging from a tree in the Hundred Acre Woods. The reasons for Eeyore’s depression are never mentioned, leading me to believe that something very bad happened in his past, like he drove a busload of kids over a cliff and was the only survivor. The other scenario is that he lacks the correct chemicals in the brain that cause happiness and should be medicated immediately. Either way, he is one unhappy horse.

2. Strong Sad

With his grey body and elephant legs, Strong Sad is the living embodiment of sadness. One of the Brothers Strong from Homestar Runner, he wallows in a pit of misery 24 hours a day, writing poetry and blinking. His chronic depression is so acute he hardly ever moves. His voice is as soft as the last snowflake on a hot duvet. He has no teeth. Strong Sad’s life is a hell of introspection, longing and being pummelled. Let me just say, out of all the people on this list, this is the one I’d least like to hang out with. He would drone incessantly about minor illnesses and how it’s getting dark earlier each evening. If I wanted that, I’d call my mother.

1. Charlie Brown

The saddest cartoon character of all-time, no doubt. The dutiful, long-suffering owner of Snoopy in the comic strip Peanuts is dealt a heavy dose of real life, and boy, does he feel it. We all know being a kid is tough, but rarely do the stories we tell ever mention that fact. It’s like something adults have forgotten, or a hidden secret parents don’t want you to know. Well, Peanuts knew. The strip demonstrated the struggle, pain and downright misery of childhood, all through one hapless individual; Charlie Brown.

He was born without good looks or discernible talents, constantly ignored or put down by others, and yet his heart remained filled with trust, hope and ambition. He dreamed of being great at baseball, yet could barely scrape a team together (and when he did, they got beaten, and he took the blame). He never received Valentine’s cards. His dog couldn’t remember his name. He had the football pulled away from him at the last minute. I feel sad just typing this. Charlie Brown, for all intents and purposes, was a loser. But the good news, as demonstrated by Charles M. Schulz, is that life is a many splendored thing, and while it contains a huge amount of sadness, it also contains friends, joy, uncertainty and pumpkins. Feeling sad is just one of the aspects of being human, and in that regard Charlie Brown lives on, inside the hearts of every one of us.

You may also like...

10 Responses

  1. PopCultureFiend says:

    You forgot Hardy Har Har, the clinically depressed laughing hyena and sidekick to Lippy the Lion

  2. Love Strong Sad. Possibly my favorite of the newest sad cartoon characters. However, generally, my absolute favorite new cartoon character in the world has to be Lumpy Space Princess from Adventure Time. Truly no better character exists today.

  3. shaun says:

    how about bill dauterive of king of the hill the guy tries to kill himself in numerous episodes lol he is def the best one

  4. *Snicker* says:

    Courage the cowardly dog was pretty sad for a kids show.

  5. minx says:

    bill dauterive and zoidberg are as sad as it gets especially since they both are so sweet & nice you cant help but feel bad for them :<

  6. Tangre says:

    Hello? Squidward Tentacles? How many kids cartoons have a character say “too bad that didn’t kill me” or “i knew i shouldn’t have gotten out of bed today”

  7. Helpful info. Fortunate me I found your web site unintentionally, and I am
    surprised why this accident didn’t took place in advance!
    I bookmarked it.

  8. Max Conners says:

    LoL at all of the above. Ive got 1 for you that goes back to the 1960’s. Look for the Gulliver’s Travels character Glum. He needs therapy.

  9. Gary Pitt II says:

    You must not have ever seen the 1968 cartoon the the adventures of gulliver.

  1. August 31, 2015

    […] Warner Bros. / Via […]

Leave a Reply

Your email address will not be published. Required fields are marked *