Alternate Character Interpretation: Just how clueless was Owl when making the map? One of the places he marks as "Peaceful Forest" on the map seems to be false until the end where we see that it truly was peaceful. Also, the way to skull was over the gorge, not through the gorge as seen on the map so the gang can't say Owl was acting goofy, considering they never truly went there to begin with.
Ass Pull: The Skullasaurus' roars actually being Pooh's tummy roaring is a bit hard to swallow, even though the gang's entire journey was over the top thanks to their fears.
Critical Dissonance: The movie earned a lot of negative reviews upon release thanks to its rather dark and serious tone, especially for a movie about such a kid-friendly franchise as Pooh. Despite this, however, it's one of the most beloved and memorable Pooh movies among Pooh fans, partially because of said darker and serious tone.
This is somewhat downplayed, though, by the fact that only eight critics bothered to rate it.
As noted below, Owl's song "Adventure Is A Wonderful Thing" is a whimsical, wacky, nightmarishly fun song about his romantic views of adventure.
"Everything Is Right", for being the triumphant, euphoric return to the sanctuary of the Hundred Acre Wood after all the danger and drama of the gang's life-changing journey.
Carl Johnson's score can really pack a punch, as the most emotional scenes are carried well by his themes. Christopher Robin's theme is bittersweet but still so full of love; the final cue as the story ends has the appropriate gravitas and dramatic swell for such a heavy story; and the music of the more perilous parts of the film is pretty creepy indeed.
Ear Worm: "If it Says So", theeeen it is so! If it is so, so it iiiiiiiis!
Tigger waving goodbye at the end is pretty emotional these days since this was the last film in which Paul Winchell voiced Tigger (though not the last time he voiced the character overall, he would play him again in A Winnie The Pooh Thanksgiving and Winnie The Pooh: A Valentine For You, though both times, Jim Cummings had to do Tigger's singing. He would have voiced Tigger again in The Tigger Movie, but his voice had become a bit too scratchy by that point, and he was passed on in favor of Jim Cummings. The Disney Imagineers, who felt bad for him, gave him one last chance to voice Tigger in the "Many Adventures Of Winnie The Pooh" ride at Disneyworld).
The same goes for Christopher Robin. Apparently when Disney made this movie, they really did mean it as a semi-goodbye to the character because he's rarely had a prominent role since this film!
He Really Can Act: The entire cast gets to really show off their acting chops in this movie as their characters are taken to dramatic places they've never been before, especially Jim Cummings (Pooh) and Ken Sansom (Rabbit).
Memetic Mutation: Pooh's innocent dithering of Christopher Robin attempting to tell him some bad news is now cited in memes as the way most folks try to deal with things.
Nightmare Retardant: Zigzagged with The Reveal that the Skullasaurus was never real and that the places the gang had ventured were not scary at all. On one hand The Reveal doesn't lessen the dramatic experience the gang has endured and has grown from, on the other hand, a lot of the Nightmare Fuel for the film loses some water since most of it wasn't real. However, Tropes Are Not Bad considering that the final song in which the gang happily returns safely home is a Crowning Moment of Heartwarming since they've conquered their fears and completed their journey.
True Art Is Angsty: By far one of the darkest anything to come out of the franchise, and widely regarded as one of the best movies in the franchise, and one of the few good Direct-to-Video sequels Disney has done.