Top Ten Winnie the Pooh VillainsThe Winnie the Pooh franchise isn't really well known for it's villains, so when any character that shows up bearing any sort of resentment or malice towards Pooh and his friends makes an appearance, they prove to be an interesting bunch in a mostly lighthearted and (villain-less) Disney franchise...
A cunning honey thief/kidnapper who makes his debut in The New Adventures of Winnie the Pooh along with his partner in crime Heff. The only officially named Woozle character to appear in the series. Voiced by Ken Sansom who also was the iconic voice of Rabbit.
Stan's slow-witted, honey thieving heffalump in crime. Voiced by Chuck McCann.
The main antagonist of The New Adventures of Winnie the Pooh episode Cleanliness Is Next to Impossible. A giant slime monster plotting the take over the world by making it dirty from his lair underneath Christopher Robin's bed. A surprisingly creepy and terrifying villain by Winnie the Pooh standards, and by far the most evil real character to ever appear in the entire franchise. Voiced by Jim Cummings.
The main antagonist of The New Adventures of Winnie the Pooh episode Paw and Order. A literal Horse-Thief who antagonizes Pooh and his friends in the western play they're putting on. Voiced by Jim Cummings.
The secondary recurring antagonist of the 2003 video game Piglet's Big Game. A frightening evil door who repeatedly comes face to face with Piglet to try and scare him away. Voiced by an unknown voice actor, (but it was probably Jim Cummings...)
The main antagonist of the 2011 Winnie the Pooh movie. Despite his heavily exaggerated very features, he turns out to be very real, albeit much less evil than theorized by Pooh and his friends. Voiced by the late Huell Howser who sadly passed away a few years after the film was released.
A trio of gangster style Pooh, Piglet, and Tigger lookalike toys who appear in the The New Adventures of Winnie the Pooh episode How Much Is That Rabbit in the Window? They aim to steal a "special" tag from Rabbit to try and get bought by Chrtistoper Robin. Voiced by Jim Cummings, Ken Sansom, and Chuck McCann respectively.
A trio of thieving pesky rats who appear in The New Adventures of Winnie the Pooh. They have a habit of always replacing their stolen goods with walnuts. All voiced by Frank Welker.
Neither the Skullasaurus nor the Jagulars are real. I didn't add them for a reason...
The main antagonist of the 2003 video game Piglet's Big Game. A truly frightening shadowy beast indeed. Appears in the final level A Blustery Day as the the true final boss of the game.
The main antagonist of the episode Tigger Gets Bounced in the 2007 Winnie the Pooh series My Friends Tigger & Pooh. A bouncing robot created by Rabbit that goes on a violent rampage after getting wet. Considering My Friends Tigger & Pooh is an incredibly kid-friendly series, even by Winnie the Pooh standards, having any real actually threatening antagonist make any sort of appearance in it is quite a surprise...