Heff Heffalump and Stan Woozle
Heffalump and Woozle in the flesh. Bumbling gangster types who are constantly after the Hundred Acre Wood's honey supply. Appeared as recurring antagonists in New Adventures.
- Alliterative Name: Heff Heffalump, to the point that his first name seems just an abbreviation of his last name.
- Big Eater: They swipe the entire wood's supply of honey in one night.
- Cruel Elephant: Heff is an antagonistic toy elephant.
- Dumb Muscle: Heff is bigger and stronger than Stan, but pretty dimwitted.
- Harmless Villain: They sneak into your house at night and rob you dry...of all your honey!!!
- Ineffectual Sympathetic Villain: Being up against Pooh of all people almost makes them look competent, but ultimately they're still petty buffoons who suffer slapstick failure.
- Minion with an F in Evil: Heff is noticeably dumber and less conniving than Stan, though not to the extent of Dumb Is Good, as he's still an unrepentant honey-thief.
- Obviously Evil: Stan clearly looks sinister and malicious, even for being a stuffed weasel.
- Real After All: Heffalumps and Woozles were suggested to be mere imaginary threats thought up by Pooh and the others in the original books and Disney material preceding this.
- Schemer: Stan is the brains of the operation and makes all the decisions and ideas.
- Species Surname: They are, indeed, a Heffalump and a Woozle.
- Those Two Bad Guys: They're always seen together and are the villainous characters who show up the most.
- Why Did It Have to Be Snakes?: Being a toy elephant in a Disney show, Heff is absolutely terrified of mice, and in the best Disney tradition, this makes him helpless when faced with Roo or Kanga, who he mistakes for giant mice.
- Wicked Weasel: Stan is an antagonistic toy weasel.
- With Catlike Tread: Though, fortunately, the denizens of the Hundred Acre Wood are silly enough that the two manage to be surprisingly good at stealth even with their propensity to give themselves away while hiding.
- Yellow Eyes of Sneakiness: Stan has these.
Hulking, thuggish Woozle who only appeared in the New Adventures episode "The Great Honey Pot Robbery".
- Attack of the 50-Foot Whatever: He's enormous, big enough to push over trees or squash any of the heroes like a bug.
- The Brute: Stan and Heff initially recruit him to be the muscle in order to defeat Pooh and friends so they can steal all their honey.
- The Dreaded: Heff is absolutely terrified at the prospect of calling Wooster out to help, and once they see him, almost everyone is equally scared... except Winnie the Pooh.
- Face of a Thug: He has a very round, squashed-in, ugly, brutish sort of face that emphasizes his ogre-like status amongst the Woozles.
- Gentle Giant: After his HeelFace Turn, he shows he can actually be a very gentle and friendly individual.
- HeelFace Turn: After Pooh offers to be his friend, Wooster decides to politely ask for honey rather than steal it.
- Hulk Speak: Wooster has a noticeably simplified manner of speech that roughly fits this trope.
- Knight of Cerebus: He's pretty frightening by the show's standards, at least until his HeelFace Turn.
- Never Learned to Read: Pointed out by Stan when Wooster ignores a sign pointing towards an Obvious Trap set up by Rabbit.
- Top-Heavy Guy: A truly exaggerated and frightening example; Wooster's body seems to be all barrel chest and muscular arms, tottering along on comparatively tiny little legs.
- Tiny-Headed Behemoth: His head actually isn't too small, but on his massive shoulders, it looks ridiculously undersized.
BrunoA clockwork gorilla who appears in the New Adventures episode/segment, "Monkey See, Monkey Do Better". Initially appearing in a birthday box on Christopher Robin's bed, when the others unwrap him, he proceeds to proclaim himself "the best toy a kid could get" and proceeds to show them up by outdoing each and every one of them. Distraught, the others prepare to leave, only to find out that they misunderstood Christopher's words; he wasn't a present for Christopher, he was a present Christopher was going to give someone else. Realizing his mistake, Bruno allows himself to be rewrapped in order to be sent on to his real home.
- Catchphrase: "The best toy" and "the best present a kid could get"; he repeats variants of these constantly throughout the episode.
- Driven to Suicide: Yes, in a Pooh cartoon! Towards the episode's climax, Bruno hears Christopher telling the other toys that he's not keeping Bruno. The gorilla is so shocked and aghast at this that he proceeds to wander off into the Hundred Acre Wood and pulls out his key, slumping over on a log as he basically dies. He is found and rewound a few minutes later, but still, it's quite creepy.
- Everything's Better with Monkeys: His array of awesome tricks and abilities is intended to invoke this. To be fair to the guy, he would actually be a pretty damn great toy; it's his attitude that makes him a problem.
- Extreme Omnivore: When outdoing Pooh at gathering honey, Bruno eats the entire hive, waxy shell and all, then blows the bemused bees out of his ears.
- Gary Stu: This is how he's seen In-Universe; no matter what Pooh and his friends try to do in order to prove they're special, Bruno outdoes them.
- Hero Antagonist: Bruno isn't really a villainous character, though he is kind of an arrogant jerk, but he drives the whole plot of the episode by scaring the other toys into believing Christopher Robin will get rid of them if they're not as special as Bruno is.
- Inferiority Superiority Complex: He's so assured he's the perfect toy that when he believes he's been rejected by Christopher Robin, he tries to deactivate himself in disillusionment.
- Jerkass: Not only is he full of himself, he belittles the other toys and gets them into challenges to prove his superiority to them.
- Killer Gorilla: Not literally, but he still fits the spirit of the trope by being a gorilla who's a trouble-making antagonistic character.
- Meaningful Name: Not Bruno himself, but his episode; "monkey see, monkey do" is a now rather old-fashioned saying about mimicking someone else's talents or achievements. This monkey sees something done, and then goes out of his way to do it better.
- Small Name, Big Ego: His huge ego is his most defining trait; he manages to outdo Tigger at being full of himself. His sheer arrogance drives the whole plot of his episode, and when he hears that Christopher Robin apparently doesn't want him, he has a full-fledged breakdown that leaves him... well, see Driven to Suicide.
The Pack RatsA trio of rodents in New Adventures who compulsively steal anything that isn't nailed down, replacing them with walnuts as "payment". The gray one is the leader, the orange one is an overweight dimwit and the brown one has a slight attitude problem.
- Calling Card: They leave walnuts in place of whatever they take.
- Color-Coded for Your Convenience: Each specific memeber of the group is colored a specific hue so you can easily tell them apart.
- Goldfish Poop Gang: They're even less intimidating than Stan and Heff!
- Harmless Villains: Even by the standards of this show, they're pretty pathetic. They're not even realy out to be bad, they just can't help but steal stuff.
- HeelFace Revolving Door: They can be quite helpful at times, but can't fight the urge to continue stealing.
- Punny Name: A pack rat is an American rodent that obsessively gathers various oddments in its nest. So, we have the "Pack Rats", who're actual rats who obsessively steal anything and everything that catches their eyes.
- Rule of Three: They're always shown in a group of three, and they fit the standard "three characters" archetypes.
- Terrible Trio: They're three villains who're never seen apart from each other.
- Villain Decay: Mild example, but the Packrats are slightly more threatening in their first appearance, "Nothing but the Tooth", than in the other two episodes featuring them.
- You Dirty Rat!: They're rats who're compulsive thieves and villains, if minor ones.
An army of green, caterpillar-like insects who are forever attempting to devour Rabbit's garden in the New Adventures series. Their unnamed leader wears a bicorn hat and epaulettes, evoking Napoleon Bonaparte, and affects the mannerisms of a general.
- Voiced by: Jim Cummings
Horrifying One Shot villain from the The New Adventures of Winnie the Pooh episode "Cleanliness is Next to Impossible".
- Eldritch Abomination: By Winnie the Pooh standards, at least.
- Evil Is Hammy: Courtesy of Jim Cummings.
- Laughably Evil: Even with his slightly horrific concept, he has a rather petty comical demeanor. His motives are solely to create trash, after all.
- Killed Off for Real: Both he and his minion Smudge get sucked into Christopher Robin's vacuum, making them the only characters in the entire Winnie the Pooh franchise to die permanently.
- Knight of Cerebus: Goofy a villain as he seems to be, he's still a lot darker and edgier than you'd ever expect to see in a Winnie the Pooh story.
- Trash of the Titans: Taken to villainous extremes, creating a monster that wants to spread mess all over the world.
- Vile Villain, Saccharine Show: Well, sort of. By normal media standards, he is merely a Laughably Evil cartoon blob who wants to make the world messy, but by the usual standards of the Winnie The Pooh universe (that usually doesn't even have actual villains) he's actually kinda unsettling.
- Voiced by: Jim Cummings
The leader of the Horse Thieves. One Shot villain from "Paw and Order"
- HeelFace Turn: He ceases all hostilities against the gang when Piglet makes him the sheriff.
- Laughably Evil: Given the show, he attacks the gang with things like ice cream.
- Names to Run Away from Really Fast: Lampshaded by Piglet.
- No Celebrities Were Harmed: Vocally, Jack behaves like Jack Nicholson when he is an outlaw. He then switches to John Wayne when Piglet makes him sheriff.
- Not-So-Harmless Villain: Introducing himself as a Visual Pun, he's not the most sinister antagonist the Pooh cast's came along, but he is one of the most crafty, keeping one step ahead of them up until Piglet coerces him into a HeelFace Turn. They even complain he's too savvy to follow the script.
- Top-Heavy Guy: He's all chest, with big arms but tiny legs. That might make sense for Funny Animals of some species, but a horse?
- Visual Pun: He's not a horse thief, he's a Horse Thief (the name of his gang).
- Worthy Opponent: Sees the Masked Bear as this, deciding to get serious when he poises a threat to his control over the town.
- Voiced by: Huell Howser
A creature that Owl imagines when being asked to read a note from Christopher Robin, ending up mistaking the words "back soon" for "Backson." First mentioned in The House at Pooh Corner, but made its animated debut (with more detailed characterization) in the 2011 Winnie the Pooh film.
- Adaptation Expansion: The only thing we learn about the Backson in the novel is that it's busy with something, and that it may or may not be Spotted or Herbaceous. In the movie, we get a lot more (mis)information about the creature and even see it in person.
- Adaptational Villainy: Of sorts. In the original novel, Owl and Rabbit just imagine him as a mysterious friend of Christopher Robin's, but in the Disney version Owl instead thinks he's an evil monster who's captured Christopher Robin. Subverted when it turns out the real Backson is actually a Nice Guy.
- Blinding Bangs: His eyes are covered by his hair.
- Bread, Eggs, Milk, Squick: Everything that Owl claims the Backson does is worthy only of Poke the Poodle, except for "Stealing your youth", which is pretty dangerous, and "Chipping your tooth", which obviously, would be pretty painful.
- Dark Is Not Evil: He initially appears pretty fearsome, but it turns out he's a rather pleasant guy.
- Disney Acid Sequence: The Backson Song, in classic Disney tradition, involves lots of weird, out-there events and backdrops.
- Felony Misdemeanor: Everything the characters blame the Backson to be committing during its musical sequence are rather unfantastical and mundane, such as "scribbling in all your books", getting you to sleep in, spilling your tea, interrupting your train of thought, and never saying "pardon" when it bumps into you. It's also averted, as they also claim that it chips your tooth and steals your youth!
- Real After All: The Backson makes an appearance in the post-credits stinger of the movie, but he seems to be a rather cheerful fellow.
- The Stinger: The Backson stomps along through the woods, looking menacing, and then comes across the objects trail that Pooh and friends left, and cheerfully proclaims about how you can find so many interesting things in the woods. He sees the picture of himself, thinks everything must belong to the guy in the picture, and proceeds to pick up the items, leading right into the pit and falling into it.
- "The Villain Sucks" Song: The Backson Song, which is all about what a monstrous, evil fellow he is.