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10 Weirdest Winnie the Pooh Moments In Disney History

Winnie the Pooh is a heartwarming Disney creation about a honey-loving bear and his pals in the Hundred Acre Wood. But these moments are just bizarre.

Winnie the Pooh and his Hundred Acre crew are some of the most beloved and cherished characters to come from Disney. While the words "weird," "strange," or "unusual" don't often go together when describing this franchise, you'd be surprised by how many of Pooh's adventures venture towards the wild side.

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The magic of Disney can be a double-edged sword; it can create colorful worlds of whimsy and wonder, but it can also spawn some serious nightmare fuel. Even the likes of Pooh and company are not immune to some odd and unusual adventures. Don't believe us? Have a look at our list to see how bizarre the Hundred Acre Wood can get.

10 Heffalumps and Woozles

To be fair, it was the '70s, and psychedelic imagery was the thing to do in your big animated features — Disney was not exempt from the rule. After Tigger warns the silly old bear about the dangers of honey-hungry Heffalumps and Woozles, the Disney artists treat us to a very catchy, pink elephants-inspired nightmare sequence.

"They're far, they're near, they're gone, they're here, they're quick and slick and insincere." They're the Heffalumps and Woozles, and they're easily one of the most memorable elements in Winnie the Pooh and the Blustery Day. Not exactly something A.A. Milne would do, but we're not complaining.

9 Rabbit's Forest Freakout

One of the best things animation can do is express emotional concepts like happiness, love, or in Rabbit's case, fear and anxiety. When trying to lose Tigger in a dark and misty forest, Rabbit gets lost and can't find his way back out. Soon enough, his imagination begins to run away with him.

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What happens next is a brief but trippy sequence that gets Rabbit more than a little jumpy. His nerves are so fried, a pond of croaking frogs, a munching caterpillar, and other night sounds send him into full-on hysterics. It's a short scene, but definitely still strange.

8 Adventure is a Wonderful Thing

Pooh's Grand Adventure: The Search for Christopher Robin is definitely one of our all-time favorite Pooh flicks, but it's also the absolute darkest, sending the friends on a daunting adventure into "The Great Unknown." No sequence represents this film's mood and tone more than Owl's song "Adventure is a Wonderful Thing."

This bombastic musical number sees the friends in a fantasy sequence on Owl's hand-drawn map, facing off against various environments. They're also menaced by monsters, spun in all four directions, and nearly mummified. The use of frightening visuals in this song is just a taste of the things to come for this unusual adventure of Winnie the Pooh.

7 Round My Family Tree

Snappy Sherman Brothers song aside, Tigger's big, bombastic musical number in The Tigger Movie is absolutely stuffed with some strange and stripey images that we never thought we'd see in the Hundred Acre Wood. Ever see a Tigger-fied version of the Country Bear Jamboree, the Brady Bunch, or Marilyn Monroe? You have now.

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We've gotta give the Disney artists a little extra credit here — it's pretty inventive to see how many different scenarios they can put Tiggers in. The circus trapeze act, football game, and Wild West setting we can all believe pretty easily, but a Jerry Springer episode and a big Vegas show number? Yeah, this isn't exactly your typical Tigger theme.

6 I Wanna Scare Myself

Yet another strange and unusual Tigger number has to be "I Wanna Scare Myself" from Boo to You Too, Winnie the Pooh. When one thinks of a Hundred Acre Wood Halloween, images of Pooh and company in homemade costumes with cutesy Jack-o-lanterns are normally what comes to mind, not Tigger surrounded by all manner of freaky monsters.

Heffalumps, Woozles, ghosts, and even the Headless Horseman make an appearance in this fright-tastic fantasy Tigger has on Halloween night. We know he's always been the oddball of Pooh's posse, but now we know he's extra proud of it. What's Halloween without at least one scare?

5 Tribe of Pygmy Piglets

The New Adventures of Winnie the Pooh was a classic of '90s era series that put Pooh and his friends in strange and sometimes perilous scenarios, many of which make this list. How about we start with the entire civilization of pygmy Piglets located in a jungle just a musical number away from the Hundred Acre Wood?

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We're not talking about a dense patch of woods here; we're talking a full-grown jungle complete with wildlife and a tribe of Piglets who tend the Land of Milk and Honey. We've got so many questions about this, it boggles our mind. We want answers, Disney!

4 Wooster the Giant Woozle

Okay, the tribe of Pygmy Piglets was acceptable after a certain point, but how in the name of the Hundred Acre Wood do you explain this guy? In the series, Stan and Heff are the show's on-and-off antagonists, and members of the woods' Heffalump and Woozle community. When one of their honey-snatching schemes falls through, they enlist the help of an absolutely ginormous Woozle named Wooster.

The dude is a titan among Woozles, toppling over trees and obstacles in his wake. How does something this huge and monstrous inhabit the same world as Winnie the Pooh? Thankfully, Pooh's able to win him over with the power of friendship. We'd hate to have that guy as an enemy.

3 Crud

You could make the argument that the following is a product of Christopher Robin's overactive imagination, but we'd be skeptical to think that the same imagination that created Pooh and his friends created the nightmare fuel that is Crud. Pooh's normal adventures see him and his friends frolicking in the woods, not doing battle against evil monsters.

Crud is the manifestation of all the dirt and filth that lives under Christopher Robin's bed, who enslaves lost toys to build a mess-making anti vacuum cleaner to take over the world. Does this sound anything like a Pooh-focused escapade? Not in our books.

2 Everything is Honey

Not nearly as drastic as Crud, but one we had to put on our list. How many Winnie the Pooh outings feature Pooh having a honey-hunger-induced hallucination complete with a fully choreographed musical number? Pooh has always had a very vivid imagination, but when it bleeds over onto the pages of the book...we take notice.

Not only does Pooh imagine a honey-made world for him to gorge on, but a set of honey doppelgangers to dance with, one of which he eats. It's all honey and bees until the fantasy ends with Pooh eating a mouthful of mud. Definitely a pink elephant-level scene in our book.

1 Their Live-Action Counterparts

Winnie the Pooh in Christopher Robin

The Christopher Robin film is a strange but enjoyable live-action Disney adventure. It's essentially a "live-action-remake" of the Winnie the Pooh flicks, showing an adult Christopher Robin reuniting with his childhood friends. This is all well and good, but Disney takes a big misstep by making the animal characters too realistic.

We would've been fine with a version of the original stuffed animals or a design inspired by the animated versions. Unfortunately, Disney tried to do both. The result is a hodgepodge of weird. Pooh has dead eyes that never blink, Tigger looks like a sock puppet version of the cartoon, and it's weird to hear the familiar voices come out of these CGI creatures.

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