Pooh's Grand Adventure is not only the darkest installment ever released in the Winnie the Pooh franchise. It's also perhaps the saddest.
- The song "Wherever You Are". Especially the end credits version, which sounds insanely sadder than you would expect from this kind of film. While the lyrics may only just fly over the heads of their young listeners, paying attention to them reveals that the song is all about Pooh's trauma at being seemingly lost and abandoned.
Pooh: I've tried to find you, Christopher Robin.Rabbit: I-I know, Pooh. I'm sorry. You'd have found him by now if I hadn't I— [notices Pooh's gone] Pooh? Pooh Bear?(Rabbit steps at the end of the cave seeing a very depressed Pooh out alone in the mist)Pooh: I've looked all the places you weren't. I just can't find the places... you are. I only know that you are where I'm not. And...Where am I? I wish you were here to tell me. Perhaps...If I were to wish very, very...hard.
- "I used to believe in forever, but forever is too good to be true..."
- Right before the song when Rabbit notices Pooh sadly alone outside the cave.
Pooh: I can only dream of you wherever you are... I'll hear you laugh, I'll see you smile. I'll be with you... just for a while. But when the morning comes, and the sun begins to rise... I will lose you. Because it's just a dream, and when I open up my eyes I will lose you.
- Pooh climbs to the top of a nearby tree and looks into the night sky, singing to the absent Christopher Robin. At one point, some clouds take the shape of Christopher, and Pooh happily chases them to the end of the tallest tree branch... but just as he nearly touches the imaginary Christopher's hand, it fades away and leaves him behind. The lyrics as this happens do not help one bit.
I'm out here in the dark, all alone and wide awake, come and find me...I'm empty and I'm cold, and my heart's about to break; come and find me...
- Also pay attention to the tree in question. It resembles the one Pooh and Christopher Robin were climbing at the beginning and the end of the movie, only this tree is a lot more dead and empty looking. Almost like it's symbolizing the times when Christopher Robin and Pooh were together.
- Right from the opening lines, this song is brutal.
- Then after the song where a very sad Pooh falls asleep, Rabbit approaches and gives the Map to him as a blanket.
- At the second act, where Pooh and friends are crossing the Despair Event Horizon. It's probably the saddest moment in all of the Pooh movies.Rabbit: I don't know where we are, and where we aren't. And I haven't known for hours. (sighs) I've failed us all.Pooh: (pats Rabbit's shoulder) I believe I have as well.Tigger: Let's face it. Without Christopher Robin, we don't have a chance of finding Christopher Robin.(Eeyore bows his head out of genuine sadness instead of his trademark gloominess, Piglet clings onto Eeyore's tail, and the others simply slump or fall to their knees)
- The absolutely harrowing obstacles Pooh and friends are forced to endure. They're just children's toys, for crying out loud, and they even accept Pooh's apparent death.
- Piglet sadly having to wander off on his own in Skull when the gang splits up.
- Eeyore screaming for his life as he plummets from a ledge and then runs in terror when he's spooked by Piglet.
- Any time Pooh laments having lost Christopher Robin.Pooh: Piglet! Come back!, I can't lose you too!Pooh: Christopher Robin? Are you here? ... Are you there? Are you... Anywhere?
- After Pooh saves him from the butterflies, Piglet is heartbroken that he was so afraid Pooh had to endanger himself to save him.
- Tigger giving up in the gorge, and eventually accepting help when he sees his friends having gone to such lengths to save him and each other.
- Christopher Robin leaving Pooh with his Arc Words. It's clear it's killing him to even try to work up the courage to say goodbye, and ends up not being able to do so. And poor Pooh just falls asleep thinking he'll play with his best friend again the next day. And it's made clear that he won't see him everyday anymore from here on out, since Christopher is indeed growing up.
- Pooh hopelessly trapped in a deep slippery ravine with no way to climb out.Pooh: Oh, bother. I believe if there's no way out, then I shall have to stay in. With no more friends. No more Christopher Robin. No more...we.
- Forever and Ever, an incredibly painful song full of Pooh Tempting Fate.
- A meta-example: This was Paul Winchell's final film performance as Tigger.