Winnie the Pooh was first created in the 1920s by author A.A. Milne, but the Pooh we’ve come to know and love and see on pretty much every kind of merchandise related to the bear didn’t make an appearance until 1966, five years after Disney received the rights to license the character, as well as all of his friends!
Winnie the Pooh has been a mainstay of many people’s childhoods and, with the help of some very talented artists, we’re about to mess up all those memories right now!
As a cartoon bear, Pooh has never embraced the wild nature that being a bear would entail, but many of these fan art redesigns seek to rectify that error, and in doing so, transforming the honey-loving chubby toy into something a lot more vicious. Be warned: these images are not for the faint of heart.
16 This Bigger Bear
We all know that Winnie the Pooh is a fan of food, particularly honey. However, seeing Winnie fall prey to his love of the sweet stuff takes on a much more sinister notion in this piece of fan art, where we see that he’s let his sweet tooth run away with him!
15 This Bear Beatdown
Winnie the Pooh and Piglet are the best of friends in A.A. Milne’s story series (and all the Disney merchandise that came later), which is why it’s so jarring to see them attack one another in this illustration! Not only are both characters super buff, Winnie’s got a more realistic (and fearsome!) bear visage, complete with sharp teeth!
14 This Flaming Animal
A digital illustration unlike some of the pencil sketches or 2D renderings we usually see, this artist opted to show what lies beneath Winnie the Pooh’s cuddly exterior – by lighting him on fire! Seeing the button eye juxtaposed with visible ribs and bones gives us the creeps – we can’t imagine Christopher Robin would approve!
13 This Sci-Fi Interpretation
Opting to keep the traditional look of Winnie the Pooh as we know him from countless toys, backpacks, and T-shirts, this artistic interpretation also mashes up the cuddly cartoon with something way creepier – the mouth of the Predator from the bloodthirsty sci-fi Predator franchise! That’s one way to get all the honey you could ever want!
12 This Honey Addict
In a series of illustrations from artist Paul Ribera, he imagined the characters of Winnie the Pooh to be representative of different mental illnesses or disorders. For example, Rabbit was afflicted with OCD while Piglet dealt with severe anxiety and Tigger battled ADHD! For Winnie the Pooh, always a fan of indulging, Ribera saddled him with an eating disorder, as seen in this ghoulish sketch.
11 This Realistic Version
Winnie the Pooh is about as unrealistic a bear as is possible to be, from wearing a T-shirt (and no pants) to talking to his generally cuddly demeanor. Designed by French digital artist Sylvain Sarrailh as part of his “Bada** Cartoons” collection, this Winnie is a lot more realistic – even though he’s still wearing clothes. Clearly, he isn’t a fan of Christopher Robin anymore!
10 This Fierce Fella
There’s bears being frightening and fierce, and then there’s this bear, which looks like he will hunt down and destroy us and everyone we’ve ever loved. Those eyes are giving us the creeps! If it weren’t for the pot of honey at his feet and the torn red shirt, we might not have guessed that this was our beloved Winnie the Pooh!
9 This BBQ-ing Bear
Piglet is definitely a cutie, but we understand that his constant nagging might wear a little thin after a while. Perhaps that’s why, in this dark redesign, a fan has chosen to show Winnie fed up with Piglet’s neuroses and opting to put him on a spit to keep him quiet once and for all! Yikes!
8 This Allergy-Addled Version
How twisted would it be that if the one thing Pooh loved was the one thing he couldn’t have? It would be honey in his case, and yet, in this fan redesign, he still can’t help himself from digging into a pot of the sticky stuff, even as the bees attack him and he puffs up with all sorts of blisters!
7 This Human Version
We appreciate that some artists want to imagine animal cartoon characters as humans, and it can be a really fun experiment! That being said, making Pooh into some buff anime god makes us feel all sorts of icky. Pooh is never a “hot” character, and turning him into some ripped Adonis just feels all sorts of wrong.
6 This Drooling Cartoon
Winnie the Pooh is all snuggles and softness, which is why we’re so grossed out at this interpretation from artist Simon Hartvig! Captioning it, “He ended his days as a honey junkie,” Hartvig certainly makes it look like Pooh has been suffering through some rough times, but that demented grin and rope of saliva are just nasty.
5 This Terrifying Bear
No stranger to transforming beloved cartoon characters into pure nightmare fuel, artist and digital illustrator Dennis Carlsson has made creepy victims of other fan faves like Tweety Bird, Pikachu, and Winnie’s friends Piglet, Tigger, and Eeyore! This image is one that sticks with you and makes you want to take a closer look at any stuffed animals you still have in your bedroom.
4 This Bodybuilding Bear
Looking like he could give any WWE wrestler or bodybuilder a run for their money, this Winnie the Pooh is way more buff than we ever wanted him to be. There’s something that makes us uncomfortable about seeing a favorite childhood cartoon transformed into this ripped humanoid version. We’ll pass, thanks.
3 This Clawed Winnie
Unlike the original Pooh’s paws, which end in harmless rounded stumps, this artist chose to make things a little more life-like with the additional of sharp bear claws as Winnie clutches at an almost-empty jar of honey. Seeing him halfway between stuffed animal and real bear cub is a little disconcerting, to say the least.
2 This Grinning Doll
If we really think about it, the idea of Winnie the Pooh and his friends – a collection of stuffed animals – walking and talking could easily be spun in a creepy manner, as this artist has done. From the clear stitching on his face to his devilish grin, we certainly wouldn’t wander into the Hundred Acre Wood and risk running into him!
1 This Bloodthirsty Bear
We kind of love this weird mashup of classic cartoon and vintage horror, especially since the artist kept the original look of the Winnie the Pooh we know so well, but added a sinister twist. In this version, Pooh is embracing the bloodlust that comes with being a bear, it’s just much creepier that he’s going after his friends!