For a Winnie the Pooh TV series, this show actually got very dark at times.
- The Nightmare Dreams had by Piglet, Rabbit and Pooh in "There's No Camp Like Home", "Rabbit Marks the Spot" and "Balloonatics", respectively.
- "Cleanliness is Next to Impossible"
- All of Christopher Robin's toys, clothes and shoes disappearing under his bed. The bed then keeps spitting out his other shoe, several times. Cue the ominous voice saying, "No more shoes, please. We already have one." When Piglet and Pooh Bear bend down to investigate, they vanish under the bed.
- The Evil Laugh when Christopher Robin and Tigger go under the bed to find Piglet and Pooh.
- The one-shot villain Crud (pictured above), a huge blob of slime who lives under Christopher Robin's bed. Jim Cummings uses the exact same voice he would later use for Robotnik in Sonic the Hedgehog (SatAM).
- Crud using Christopher Robin's toys as slaves to create an un-vacuum cleaner, which will make everything "not clean". Christopher Robin tries to save them, but the crayon soldiers stop him.
- The crayon soldiers do Crud's guard work and take anyone away who disagrees with him, including Christopher Robin.
- Christopher Robin gets locked in a tiny cage under the bed after he refuses to help Crud. There's barely enough room for him to move, so that he's forced to sit in a Troubled Fetal Position.
- The voices calling "Piiiigg-leeeeett" and Eeyore's screaming in Things That Go Piglet in the Night. Piglet is scared one night when he hears a mysterious groaning on the wind, and ends up getting caught in a pillowcase when he runs out of his house to find Pooh. Unfortunately, this leads to Pooh mistaking him for a ghost, and the whole cast (sans Tigger and Eeyeore) going on a ghost hunt. We're treated to our believed cartoon friends scared half to death in a spooky forest at night. Thankfully, it eventually turns out there is no ghost, the groaning was Eeyore trying to teach himself to use a swing.
- "The Great Honey Pot Robbery" opens with Wooster saying, "Honey" in his deep voice.
- The first glimpse we get of Wooster is also quite frightening. You only see his legs, and they make him look like a Tyrannosaurus Rex.
- The entirety of "Sorry, Wrong Slusher" is one of the most uncomfortably bizarre and darkest in terms of both theme and atmosphere.
- The story begins with Christopher Robin and the gang staying up to watch a "slusher" film. We don't see what the film involves, but everything from Tigger's description and the gang's nervous reactions indicates they're watching a slasher film in the vein of Friday the 13th! Granted, Tigger complains the villain is only using a butter knife, but it's still unnerving to imagine characters as innocent as Pooh and Piglet being exposed to something like that.
- The episode then deals with the gang thinking the Slusher is now coming to get them, due to Tigger accidentally prank-calling a neighbour. Like all adults he is entirely faceless, but we do see him as a menacing silhouette in the window. He's probably the angriest character we've ever see in the whole canon. And not helping is the barking of a "huge, horrible hungry dog" that's also apparently out to get them.
- Overall, the episode has a very surreal and dark mood to it, almost like something out of a typical bad dream one might have as a kid. Tigger and the other characters are more oblivious or mean-spirited in some ways than usual, including Christopher Robin, which gives an underlying sense of wrongness about everything.
- At some point Piglet, who is being used as bait, is so frightened he almost goes catatonic, simply frozen and staring ahead in space and stammering broken syllables in terror. And there is no point where he shakes himself out of it and grows brave for his friends. Instead he is nudged by Eeyore, which startles him so badly he just screams his poor head off and runs crying for Pooh into the darkness.
- Anytime Eeyore yells in fear in this episode, it comes across as quite frightening. In every adaption of Winnie the Pooh, we've really never heard or seen Eeyore experience any emotion other than depression, indifference, or occasionally gratitude, so hearing him yell "SLUSHER!" with genuine fright in his voice is very unexpected and scary.
- Finally, we get a nice jump scare shot with the dog's snarling reveal, the whole gang gets arrested, and even after it's all revealed a dream (Or was it?), we get struck with a Gainax Ending.
- The vacuum cleaner/dragon from "Babysitter Blues", along with Kanga's fear of child abduction.
- The recurring crows that pester Rabbit are usually portrayed as goofy tricksters who just want to steal food and have some occasional Pet the Dog moments. Not so much for the crows in "A Very, Very Large Animal". They're bigger and a lot meaner, essentially being violent bullies who have no qualms about shoving other animals off of food they want, and their actions are framed a lot more seriously and with a considerable air of menace. Even Rabbit, who normally has no qualms about chasing pests off his crops, is shown to be visibly frightened of these birds.
- Most notable is when Piglet, thinking he's now a large animal, confronts them for stealing corn from Rabbit's garden, demanding that they pick on someone their own size. The crows take him up on that offer and dogpile him ripping his height-boosting gear to pieces! The evil chuckle and eyes inexplicably turning red before their attack doesn't help, either.
- In one scene, an ant has its leg caught in a spider's web. We don't get full view of the spider itself, only huge creepy shadow looming towards the ant before Piglet rescues it.
- The climax of "Gone With the Wind." Pooh is blown around by the wind and gets stuck in a tree overlooking a cliff. The only thing keeping him from falling to his death is his scarf, which is wrapped around a branch but is starting to tear apart. All the while, he's screaming for someone to save him.
- Towards the ending of "Monkey See, Monkey Do Better", Bruno the wind-up gorilla has just overheard Christopher Robin saying he's not going to keep Bruno; leading him to depressedly wander off into a deeper part of the wood on his own, saying "he needs to unwind". He pulls his own key out of his back and throws it into the nearby undergrowth just before he shuts down; words audibly grinding away to a lower and lower pitch as he slumps over mid-sentence. This is creepy enough to a kid who sees this, but it gets worse for someone who's adult enough to realise what he's just done. In other words, we just saw a toy commit suicide on-screen by the equivalent of yanking their own heart out, remaining alive just long enough to be aware of what's happening as they die.
- In the very first episode, "Pooh Oughta Be in Pictures", there's the scene at the climax where Tigger's torn up giant carrot costume is carried off by the winds on a dark night. Pooh happens to be out walking around, and the wind causes the costume to sweep towards him, highlit on the screen like some horrific, shapeless wraith before it ensnares him. It's a genuinely scary sequence.
- The very first scene of the episode opens with Christopher Robin, Pooh, Piglet, and Tigger running for their lives in some sort of dark laboratory from some creature chasing them while growling the whole time. Yes, that's the very first thing kids tuning into the show for the first time were greeted with: seeing the main characters scared out of their minds and fleeing from some unseen danger. While it turns out to just be an Imagine Spot Christopher is having (he was actually just trying to get out of eating his carrots), it perfectly sets the tone for the show that it's going to be a bit darker than previous Pooh works by Disney.
- Although Pooh wasn’t in any real danger when the carrot costume “attacks” him, hearing him screaming for help is extremely unnerving.
- "Find Her, Keep Her"
- The episode starts with Rabbit hearing Kessie call for help from her nest, which the winter wind is blowing about. Kessie at this age can't fly, and has never left her nest. He barely manages to save her by using Pooh's honeypot as an improvised net, but not before everyone gets caught in the huge gust.
- Tigger and Kessie wind up trapped on a very tall tree, which then topples off the side of a cliff, leaving them dangling hundreds of feet off the ground with neither of them able to fly (Kessie may be a bird, but she's too young). Kessie's screams reach Rabbit and bring him running and he crawls out onto the tree despite his outright phobia of heights, Tigger swings Kessie to him- and then she falls anyway because they can't hang on to each other. Sure Owl shows up for a timely rescue, but this scene was surprisingly Mundanger-ish for such a cute show.
- "The Masked Offender" has a pretty terrifying climax where the heroes get stuck to the fake monster they created to humiliate Tigger/The Masked Offender. It rolls down the hill to a rickety bridge, only for the bridge to capsize and turn the monster upside down as the heroes begin to slowly fall into a gorge with no means of escape. Rabbit's desperate screams sum it up.
- Rabbit: Help, somebody! HELP!!!
- "Paw and Order"
- The desert is so dry, the cacti dry up as Pooh and his friends approach the town. Rabbit starts waxing lyrical about how they're going to dry up in the desert, before he's tossed into a water trough and has to ask for a towel.
- The Mass "Oh, Crap!" and Screw This, I'm Outta Here from the townspeople indicates how bad Nasty Jack and his horse thieves are.
- The former prairie dog sheriff sticking his badge onto Piglet so that Piglet has to face Nasty Jack. Piglet tries to take the badge off when Pooh Bear suggests that it wouldn't make him sheriff, but it stays stuck on for most of the episode.
- The fact that Nasty Jack wants to "trounce" little Piglet, whom he can pick up like a small child, merely because Piglet has the sheriff badge. Piglet at first only wants to leave with his friends, and he's visibly scared when Jack demonstrates the difference between "bounce" and "trounce". Later on, he makes it clear he knows that it would be a Curb-Stomp Battle, and snarks about the sheriff's "moves".
- Nasty Jack then beats up Rabbit when forcing the latter to make banana splits as a bartender, and Rabbit puts carrots on the sundaes instead of cherries.
- When the Masked Bear saves Sheriff Piglet, Jack gets wise and kidnaps the Masked Bear and his Faithful steed, tying them up and leaving them in an abandoned mine shaft. He then sends a rhyming note to Sheriff Piglet explaining that no one's coming to save him, and they're having a sunset showdown.
- At two different moments, Nasty Jack's eyes change from their usual white with black pupils to yellow with red pupils to represent his more dangerous side. The change is... unsettling to say the least.
- "Luck Amok": One of the scariest moments in the series came when Piglet is sealed in a "safety shelter" for 7 years so his bad luck won't hurt him or anyone else. That's already scary enough if you think about it, but the real fright comes when lightning strikes the shelter almost immediately (thanks to a lightning rod Tigger foolishly placed on the top) and destroys the entire shelter, leaving only Piglet left, who is so traumatized by the whole experience, he is left catatonic and whimpering with a terrified look on his face until the others assure him there's no problem. The fact that the lightning strike is accompanied by a terrifying Scare Chord only makes it more terrifying.
- In "No Rabbit's a Fortress," Rabbit tries to make a giant tower to protect his garden, but accidentally seals himself inside it with no way out. The second Rabbit realizes his mistake, he immediately begins freaking out, even crying out "I'll starve!"
