The New Adventures of Winnie the Pooh is a Disney animated series that features Pooh, Piglet, and all the rest of the Hundred Acre crew in adventures and outings that just couldn’t be contained in the pages of his storybook. It’s a piece of the ’90s that puts Pooh and company into a more modern era, but also some incredibly strange situations.
Though most episodes feature the friends doing their usual schtick in and having fun in the forest, they’re no strangers to some very out-there adventures into the realms of fantasy and the absurd. If you want to see some peculiar Pooh episodes, have a look at the 10 featured on our list.
Pooh Oughta Be in Pictures
What sort of adventure would make for a great first episode of a Pooh series? How about we see what would happen if the lovable creatures took a trip to see a horror movie? That sounds like fun, doesn’t it?
Christopher Robin takes Pooh and the gang to the theatre to see their version of a Godzilla flick where after they completely wreck the projector booth, they proceed to make their own monster movie in the Hundred Acre Woods. Seeing the animated stuffed-animals in a real-world setting is odd enough, but Pooh and monster movies is a whole new level of weird.
The Masked Offender
We’re not saying we wouldn’t want to see Tigger become a superhero, he’d pull it off with the greatest of ease. But that’s not what he does in this episode. Instead of performing acts of heroism, Tigger dons a mask and goes on a misguided adventure of mass destruction.
It’s not that we don’t enjoy watching Tigger go full fanboy, but it’s a bit odd to see him go so far overboard in his quest to “save” his friends from peril. What’s even weirder is the elaborate trap Rabbit and company set to stop him in his antics. At least Piglet got to be a sidekick.
Me and My Shadow
Seeing Piglet make friends with his shadow is cute at first, but when the shadow starts showing signs of sentience, it gets a little creepy. Not only does Piglet’s shadow run away, but the others try to cheer him up by lending him their shadows in its absence. And it doesn’t end there, folks.
Piglet eventually has to venture out into a spooky forest on his own and rescue his shadow from a pair of monstrous shadow creatures cast by some evil-looking trees. He’s successful, but the show ends with the shadow crawling over him in bed to blow out a candle. We can’t be the only ones getting Lovecraft vibes here, can we?
Babysitter Blues
The next few episodes deal with the power of an overactive imagination and nowhere is this more clear than the first half of this episode. Though it’s all in Christopher Robin’s imagination, we see some pretty strange scenarios featuring Pooh, Tigger, and Piglet.
Before the halfway mark, we see the friends in an escape from prison, a pirate ship battle, and fighting against a draconic vacuum-cleaner whilst avoiding the bane that is Christopher Robin’s babysitter. We always knew Christopher Robin had a creative mind, but this is going above and beyond the call of duty.
Sorry, Wrong Slusher
We’re willing to give this one a little wiggle room seeing that it’s all a nightmare, but it’s one of those scenarios that not only gets a bit weird but reaches rigamarole status after a certain point. After a night of TV binging, a “slusher film” gives the gang a nightmare and they resort to cartoonish antics to defend against a fictitious home invader.
If that wasn’t weird enough, the dream sequence ends with the Pooh, Tigger, Piglet, and Eeyore getting arrested by the police, interrogated, and taken to court where the judge literally throws a book at them. Christopher Robin definitely needs to avoid binge-watching for a while.
A Knight to Remember
Now we take you to a Pooh episode that’s almost entirely a literal fantasy as Piglet is whisked away to a chess-board inspired kingdom where his friends assume the roles of medieval characters, including Rabbit as a befuddled wizard, Eeyore as a dragon, and Piglet as the titular Knight to Remember.
The episode is weird to say the least, but we’d be lying if it wasn’t entertaining. Seeing Piglet trade in his makeshift armor of pots and pans for a breastplate and helmet is definitely smile-worthy, and we do see him cast his timidity aside. Now we’re wondering what would happen if they played D&D.
All’s Well That Ends Wishing Well
Ok, the last three were definitely fantasies, but this one gives us no reason to suspect that it doesn’t happen in reality. When the friends give Tigger a birthday party and Pooh can’t figure out what to give him, he tries to literally give Tigger the moon when he sees it reflected in the water of their wishing well, but ends up falling into a magical realm instead.
The friends end up in Wish Land where all of Tigger’s birthday wishes come true and Tigger goes mad with power, wishing for exaggerated versions of his birthday gifts, nearly drowning Pooh in honey and only escaping by wishing them all home. Talk about a wild birthday party…
Pooh Skies
At this point, we’re starting to question whether the Hundred Acre Wood is just a junction for other fantasy realms. When Tigger mistakenly convinces Pooh he broke the sky while trying to knock down a beehive, Pooh and Gopher must venture into the clouds to stop the sky from falling.
While the rest of the friends prepare for armageddon, Pooh and Gopher try to fix a leaking cloud machine before it floods the sky with the storm of the century. It’s a zany and surreal adventure that we’re not going to forget anytime soon. It definitely makes us question Hundred Acre physics.
The Monster Frankenpooh
Yet another case of enormous imagination, we have to include a 50ft Pooh Bear laying waste to a village in Tigger’s fireside tale. Though it’s all purely fantasy, the idea of pairing Frankenstein with the cast of Winnie the Pooh has to be pretty high on the weird-o-meter.
When Tigger barges into Piglet’s story, he turns it into a full production, starting by having Piglet’s pleasant-and-cheerful scientist character create the monster Frankenpooh. Pooh assumes the role of the creature and grows to kaiju scale once Tigger takes control. Sure, it’s a great little Halloween episode, but it’s not something we’d expect from the Hundred Acre crew.
Cleanliness is Next to Impossible
We have one question about this episode. What were the animators on? This new adventure of Winnie the Pooh is about as far from the standard as you can possibly get. When Pooh and Piglet are kidnapped by a monster under Christopher Robin’s bed, it’s up to Tigger and Christopher Robin to stop the forces of Crud.
Crud is the living personification of dust and grime who lives in a nightmare world of discarded toys and dust bunnies underneath the bed. The episode is dark and even a little creepy for a Pooh plot. Seeing the friends face off against a villainous monster is definitely not something we’d expect from this warm and fuzzy series.
