* HeyItsThatVoice: Winnie the Pooh is voiced by Sterling Holloway, who is also known to fans for playing [[Disney/{{Dumbo}} Mr. Stork]], [[Disney/{{Bambi}} Flower]], [[Disney/AliceInWonderland Chesire Cat]], [[Disney/TheJungleBook Kaa]], [[Disney/TheAristocats Roquefort]], etc.
** Rabbit is also [[Disney/TheSwordInTheStone Archimedes]].
** Eeyore was once voiced by one of the lead scriptwriters of the compilation movie, but, once he died, he was [[TheOtherDarrin replaced by]] none other than the leader of the [[TransformersGenerationOne Autobots]], [[Creator/PeterCullen Optimus Prime]] himself.
** Christopher Robin is also [[Disney/TheJungleBook Mowgli, and the narrator is Bagheera]].
** Tigger is Creator/PaulWinchell. Kind of off-putting such a fun-loving innocent character is being voiced by [[WesternAnimation/WackyRaces Dick Dastardly]] and [[Franchise/TheSmurfs Gargamel]].
** Piglet may also be known to modern audiences as [[Disney/TheEmperorsNewGroove the old guy who threw off Kuzco's groove]].
** Gopher was also [[GarfieldAndFriends Wade Duck]].
*** In ''WesternAnimation/TheNewAdventuresOfWinnieThePooh'', he's [[TaleSpin Colonel Spigot]].
** Roo (in ''Honey Tree'' and ''Blustery Day'') was a young Clint Howard.
* WhatCouldHaveBeen: Creator/WaltDisney had tapped famous Disneyland performer Wally Boag to voice Tigger in ''Blustery Day'', and Boag contributed heavily early on in the short's development to help define Tigger's personality. After Disney's death, Boag was dropped from the project in favor of Creator/PaulWinchell.