Disney Studios is known for its enriching children's entertainment which has been enchanting kids and adults alike for generations. From animated movies to cartoons and live-action shows, Disney has been at the forefront, and the Disney Channel has been a perennial source of entertainment for those who can't get enough of the movies.

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Predictably, some of the cartoons that aired on the beloved channel had some darker characters who didn't quite belong in a cheery children's show. These could be minor or major villains with devious motives, or even the protagonists themselves who had complicated histories. Their dark personalities added an edge to these Disney cartoons.

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10 Eeyore (The New Adventures Of Winnie The Pooh)

Eeyore and Owl

Sad, gloomy, and pessimistic—Eeyore the donkey has always been one of Disney Channel's most blue characters. It is not known what makes him so unhappy, but his personality looms over The New Adventures Of Winnie The Pooh and the other happy characters like a cloud.

Many fans suspect that Eeyore struggles with mental health issues like depression, as he often quotes dejected lines like "Well, I suppose it is...for some" when someone wishes him a good morning. He almost expects bad things to happen to him and accepts his fate without a word. Eeyore is clearly not doing well.

9 Riley & Todd (The Replacements)

Todd and Riley holding a magazine, The Replacements

Often considered one of Disney Channel's darkest cartoons, The Replacements allowed the protagonists, Riley and Todd, to switch out anyone they disliked at the drop of a hat. Riley and Todd are two orphans who respond to an ad for Fleemco Replacement People and thus begin their kind of terrifying journey.

Be it adults or other kids, Riley and Todd feel no remorse as they remove and replace on demand. It was a dark precedent to set for kids watching the show who were learning that they could just swap out whomever they didn't like, just like Riley and Todd were.

8 Dr. Phillium Benedict (Recess)

Dr. Phillium Benedict in Recess

Dr. Phillium may not be a supervillain on Recess, but he had some disturbing plans up his sleeve that even Ms. Finster, who disliked most kids, disapproved of. Dr. Benedict took over the school but wanted to get rid of recess completely to maximize the productivity and scores of the kids, which sounded more like labor management than running a school.

Phillium hated fun and wanted to eventually become the President of the United States of America by pulling these stunts. It takes a special kind of evil to not want kids to have time to play and relax, and his character vaguely resembled an evil capitalist tycoon.

7 DNAmy (Kim Possible)

DNamy in kim possible

DNAmy was never shown to be an evil mastermind or cruel, but her experiments were wholly unethical and extremely twisted. She used her gene-splicing to create hybrids of real animals to "cuddle" them, and her talent was often used by other mega villains like Drakken and Shego.

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Kim Possible was an awesome 2000s cartoon, but DNAmy's lack of restraint when it came to messing around with genetics was quite dark. For someone who was so audacious, her personality was simperingly sweet like a child's, which only made her creepier.

6 Stitch (Lilo & Stitch: The Series)

Stitch smiling menacingly from Lilo and Stitch

Stitch may be one of the cutest Disney creatures, but his origins and true nature were quite unfortunate. Stitch had been specially made to be a destruction machine by Dr. Jumba Jookiba, and it took a lot for him to not fall prey to that side of himself. He was supremely powerful and could be chaotic, which was why it was quite dangerous for Lilo to keep him around.

Granted, the little girl taught him how to love and be humane, but he could even harm her with his dark nature. In Lilo & Stitch: The Series, the pair had to go looking for Jumba's other experiments which was another dangerous expedition for Lilo to be a part of.

5 Butch (Recess)

Recess - Butch talking on the floor

Butch was a part of the student gang in Recess, but his aura was one of trauma and calamity. He had witnessed his brother kissing a girl, and since then had grown white hair and become gloomy and downcast, only giving messages of danger and ghosts to TJ and the group.

Butch loved to spook people out and had a scary story ready for everything: from missing balls to the feelings of bikes and buses. He definitely stood out from all the cheery kids at Third Street School, and somehow derived some pleasure from terrifying them with creepy tales.

4 Cruella De Vil (101 Dalmatians: The Series)

cruella de vil in her fur coat

Cruella De Vil was already known as a heinous puppy killer who wore their hides as coats in the 101 Dalmations movies, but she evolved into a savvy, evil corporate maven in 101 Dalmatians: The Series. It was already dark enough to see that she had no qualms about killing puppies, but when she couldn't do that, she still stuck to harassing the Dearlys so that she could take over their farm.

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Cruella files false lawsuits against the Dearly family, tries to break her marriage, pollutes the environment with her jeans factory, and even tries to open a gym in space. She is the original profiteering entity of all time who is obsessed with the pups and their family.

3 The Gross Sisters (The Proud Family)

The Gross sisters in the proud family

Nubia, Olei, and Gina formed the trio that was the Gross Sisters, who tormented the kids in The Proud Family and extorted their lunch money from them. While they seemed like run-of-the-mill bullies, their origins were actually steeped in sadness.

The Gross sisters came from a rougher side of town because their parents were not very wealthy. They were also blue in color, unlike the other characters, as their folks did not have enough money to provide them with lotion and other products. They stooped to a life of juvenile crime because of their circumstances.

2 Dr. Doofenschmirtz (Phineas & Ferb)

Perry the Platypus and Dr Doofenschmirtz

All the darkest Phineas & Ferb episodes involved Dr. Doofenschmirtz, and with good reason. His origins were dark and unfortunate, as he was constantly compared to his brighter younger brother Roger, which is likely what built resentment in him and made him a supervillain.

Doofenschmirtz's birthdays were lousy, his parents never showed up, and his inventions always wreaked havoc in his own life and in the city. Dr. Doofenschmirtz creates slaves, gets rid of love, and helps rip up the space-time continuum with his terrible schemes and inventions. He led a tragic life that made him turn to wickedness.

1 Yzma (The Emperor's New School)

Yzma

It was quite dreadful that someone who was a guardian and advisor to Emperor Kuzco, who was very young, turned on him and started scheming to get him off the throne. Yzma's methods in The Emperor's New School were also very vicious; her coterie of wild potions and sorcery could do a fair bit of damage to Kuzco.

At first, Yzma planned to turn him into a flea, put him into several boxes, mail them to herself, and then smash him to death. She had a sadistic streak in her which was terrifying, and her violence was almost always way too much.

NEXT: 10 Darkest SpongeBob SquarePants Episodes