Tear Jerker / Pooh's Grand Adventure

Pooh's Grand Adventure is not only the darkest installment ever released in the Winnie the Pooh franchise, but perhaps also the saddest.

As a Moments subpage, all spoilers are unmarked as per policy. You Have Been Warned.

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• 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.
  • "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. At first, Rabbit tries to comfort Pooh by apologizing for getting them lost, before realizing Pooh is by himself.
  Pooh: I've tried to find you, Christopher Robin.
  Rabbit: I know, Pooh. I'm sorry. You'd have found him by now if I hadn't— (notices Pooh's gone) Pooh Bear?
  (Rabbit spots Pooh outside the cave, very depressed and wandering all 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.
  • 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.
    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.
  • 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.
    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...
    "I don't know what else to do... except to try to dream of you. I wonder... if you're dreaming too... wherever you are."
  • Then after the song where a very sad Pooh falls asleep, Rabbit approaches and gives the Map to him as a blanket. Even though he shudders from the cold night, he looks up at the stars, not saying a word, but is clearly doing his best to also wish to find Christopher Robin if just for Pooh's sake.
• 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.
  • The scene starts with Rabbit frantically trying to decipher the tattered, useless map, pretending to know what he’s doing. But as his friends ask him what to do, Rabbit’s bluster fails him, and he finally breaks down from stress and self doubt, venting about how he thinks he’s not smart enough to lead the group. It can really hit home for people who succumb to stress, responsibility, and lack of self-worth. Rabbit has at times failed to take responsibility for his failures, but this time, when he protests that it’s not his fault, you know good and well that he truly is heartbroken that he can’t be of anymore help.
  Rabbit: Now if Christopher Robin were here, what would he say? Well, he'd say… (breaks and tosses the map pieces away) THAT RABBIT CAN'T FUNCTION IN THIS HUMIDITY! That it's not his fault! This fog isn't even on the map - and that... (sobs) that Rabbit is just not smart enough to know where to go, or what to do...
  • The group is appropriately distressed to witness Rabbit's mental breakdown and Pooh fails to remember Christopher Robin’s advice, leading to the official crossing of the Despair Event Horizon.
  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.
  • Speaking of crying, one book adaptation literally has the group in tears◊ when this happens. (On a particular note, this marks the only form of Disney media we've ever seen Eeyore himself actually crying.) Thankfully, in this version, they quickly end up reuniting with Pooh before Christopher Robin is found.
  Tigger: I'm gonna miss that bear. (sniffles as he pulls Rabbit off the cliff.)
  Piglet: Oh, Pooh.
• When the group ponders which way to go inside of Skull, they turn to Rabbit. However, Rabbit simply shrugs and insists they don’t look to him for advice, clearly still thinking he’s unfit to lead after his earlier breakdown.
• 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. Pooh has no idea of the awful shock he’s in store for the next day and just playfully leads Christopher Robin along like any other day, who he thinks the absolute world of. Since Pooh will never grow up, the way things are is all he’s ever and will ever know. And Christopher Robin feels the knife being twisted the entire duration of the song, not knowing how to possibly break the news to Pooh and ruin things, as happy as he is.
• The ending of the film has Christopher Robin tell Pooh that while he was away at school, he himself was just as overwhelmed and stressed in his new environment as his friends were during their journey in the Great Unknown. Any parent can tell you how difficult it can be for a young child to handle a dramatic change, especially entering a new world like going to school for the first time. Christopher Robin reveals he similarly felt like he wasn’t brave, strong, or smart enough to go on at times, which is a lot for a child to go through in just the first day of school. Thankfully, Christopher Robin explains he remembered his own advice and was able to carry on.
• At the very end, Christopher Robin asks Pooh to always be in the Hundred Acre Wood, waiting for him all the way until they’re 100 and 99, respectively. It’s bittersweet at best, but at least the love between Christopher Robin and Pooh will last the rest of their lives.
  • If one accepts this movie as The Movie of the final chapter of the original book, then this scene is the official goodbye between Pooh and Christopher Robin. All their adventures together, their lessons learned, their playtimes they’ve enjoyed, all of that is over now. And it’s all built to this single moment of bittersweet goodbyes as Pooh promises to always be here for him. David Warner’s narration also lightly implies this, noting that it’s here we leave them, and here we’ll always find them, like the ending of a book we can always pull up and reread. This is the end for Christopher Robin and Winnie the Pooh - but they’ll always be there for each other in their hearts, "forever and ever" indeed.
• The image on the back of the VHS, showing a lonely Pooh standing on the edge of a cliff while holding the honey pot in his arms, sadly looking at the night sky as a ray of light shines down on him, is downright heartbreaking.

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