For the Disney Theme Parks ride, go here.
- Accidental Nightmare Fuel: The stuffed Pooh doll winking at the audience at the film's conclusion. It's more or less probably intended to come across as cute, but many people (especially young children) who first saw that scene instead thought of it as creepy and unnerving.
- Americans Hate Tingle: While largely tolerated by many; Gopher is quite unpopular with British fans. If only because he was never in the original books (hence the quips about him "not being in the book"), but was created by Disney to give the films more appeal to American audiences. As such, he is considered symbolic of the heavy Americanization the franchise underwent when adapted by Disney. Furthermore, as gophers are native only to North and Central America, his inclusion (and the fact that he's one of the few character who's explicitly not a stuffed animal) implies that the location of the Hundred Acre Wood is the US, whereas the original books are clearly set in the UK. As a result, Gopher was excluded from the 2011 animated film and the 2018 live-action film Christopher Robin, as both were specifically designed to be a lot more faithful to the original books and thus more appealing to British audiences.
- Animation Age Ghetto: Out of all of the films in the Disney Animated Canon, this one (and its sequel, Winnie the Pooh (2011)) tends to get this treatment the worst, as even massive Disney fans can be quick to dismiss this film as being little more than a "baby/kiddy movie" due to the film's Lighter and Softer tone compared to many of Disney's other animated films. It doesn't help that Disney tends to market the Winnie the Pooh franchise to a younger demographic compared to their other franchisesnote , which only taints the film's image further.
- Big-Lipped Alligator Moment: The notorious "Heffalumps and Woozles" Disney Acid Sequence. It has a reason for why it occurs (Tigger telling Pooh about these creatures that steal honey has driven him paranoid and he falls asleep while on patrol of his house, and naturally has a nightmare about the creatures), but after Pooh wakes up, both the nightmare and the very existence of Heffalumps and Woozles aren't mentioned, as the rain storm that's now flooding Pooh's house becomes the focus. It became retroactively subverted however when later Pooh works played off of it and made Heffalumps and Woozles real characters, turning the Big Lipped Alligator Moment into a Foreshadowing.
- Broken Base: A Day For Eeyore being packaged as part of the original film. While it's considered the standard heartwarming Pooh fare standalone, some don't think it suits as a companion piece to Many Adventures due to how much it sticks out like a sore thumb from the rest visual-wise.
- First Installment Wins: While the other films in the franchise certainly aren't without their fans, Many Adventures is still, by and large, the most popular and widely beloved of the Winnie the Pooh films from Disney. One advert
for the film's 25th anniversary DVD reissue even acknowledges this, promoting it as "Pooh's first and most beloved movie". - Harsher in Hindsight: Pooh sings "I'm short and fat and proud of that" while doing his exercises in The Honey Tree. Amusing while he sang it, but not so much when his weight causes him to get stuck in Rabbit's hole.
- Hilarious in Hindsight:
- Pooh is rather deflated when the narrator tells him the last story is about Tigger rather than him. Tigger would end up the Spotlight-Stealing Squad for a large quantity of the franchise from that point on.
- Post 2007 versions of Winnie the Pooh and a Day for Eeyore have many current voice actors credited for the roles such as Jim Cummings as Winnie the Pooh despite the film retaining the original audio track. In ''The Mini Adventures of Winnie the Pooh", a clip from A Day for Eeyore (When Pooh and the gang find Eeyore in the water while playing Pooh Sticks) was indeed redubbed by the current cast!
- Improved by the Re-Cut: While the original standalone featurettes are regarded as being enjoyable, it is universally agreed by fans and critics that the combined film, The Many Adventures of Winnie the Pooh, is far better than the three original featurettes individually, since it successfully ties them together into a tight and cohesive narrative while adding new content that expands upon the narrative and gives it more depth.
- Retroactive Recognition: Tigger Too features extensive animation from Don Bluth and his soon-to-be Production Posse, and as a result, his contributions are easy to spot (particularly in the sequence where Rabbit gets lost in the woods).
- They Changed It, Now It Sucks!: A Day For Eeyore sometimes elicits this reaction from fans of the first three shorts due to substantial differences in animation, voices, and music.
- Values Dissonance: Pooh wields a shotgun at one point in Blustery Day. Granted, it’s a toy pop gun and not a real firearm, but the idea of Winnie the Pooh of all characters wielding a firearm, toy or not, would most certainly not fly today, given that firearms in kids' cartoons have become more scrutinized since the featurette's release in 1968.
- Visual Effects of Awesome: Creepy and unnerving as it is, the winking Pooh doll at the end of the film and the featurettes it was made from admittedly doesn't look that bad. The winking eyelid is carefully painted and drawn to blend in with the doll, creating a seamless and still impressive effect.
- Woolseyism: During the scene where Gopher is about to eat his midnight snack, the first thing he eats is a summer squash. Since summer squash aren't common in Latin America, the Latin Spanish dub calls the summer squash a papaya, given their similar shape.
