The movie is also the first Winnie the Pooh film (and the first Disney direct-to-video film) ever to have its special edition.
The film's plot is primarily based on two A. A. Milne stories from The House at Pooh Corner: "In which Christopher Robin and Pooh come to an Enchanted Place and we leave them there", and "In which Rabbit has a busy day and we learn what Christopher Robin does in the mornings".
- Jim Cummings – Winnie the Pooh / Skullasaurus growls / Tigger (singing role)
- Ken Sansom – Rabbit
- John Fiedler – Piglet
- Paul Winchell – Tigger (final acting role)
- Peter Cullen – Eeyore
- Brady Bluhm – Christopher Robin
- Andre Stojka – Owl
- Frankie J. Galasso – Christopher Robin (singing voice)
- Narrated by David Warner
Once upon a last day of a golden summer, Christopher Robin does not have the heart to tell Winnie the Pooh of his departure to school the next day. Although the two have fun playing the whole day, Christopher Robin is unable to tell Pooh where he's going, and leaves him with the advice, "You're braver than you believe, stronger than you seem, and smarter than you think."
The next morning, Pooh discovers a honey pot with an attached note - however, he cannot read it himself. As he goes around to his friends Piglet, Tigger, Rabbit and Eeyore, it's clear that the group needs Christopher Robin's help and advice with their own obstacles, and none of them are able to read it. From deciphering the note, Owl claims that Christopher Robin has been taken to a distant, mysterious and dangerous land called Skull against his will. Owl equips the group with a map and sends them into the "Great Unknown" of the Hundred Acre Wood, warning them of the ferocious beast that lords over Skull, the "Skullasaurus".
Soon after their departure, growls are heard off into the distance, and the group assumes that they are being pursued by the Skullasaurus. This causes all out panic and, being a "bear of very little brain", Pooh quickly proves unfit for leading his friends on this mission, leading Rabbit to assume command of the five. During their travels the group slowly realizes just how helpless they are without Christopher Robin in the outside world: In a tranquil valley outside of a forest of thorns, poor Piglet is abducted by a swarm of butterflies, making him believe he is too afraid to do anything; at a ravine, a frightened Tigger doesn't have the strength to bounce out to safety, causing all his friends to plummet with him in their attempt to retrieve him; and finally, a confused Rabbit realizes he is helpless with the map ripped in two, leaving the group lost in the mist. The group comes to terms with the fact that they are lost and helpless without Christopher Robin, but take shelter in a nearby cave. While everyone is asleep, Pooh, heartbroken, laments getting no closer to finding his dear friend Christopher Robin.
In the morning, the five realize with horror and fear that they took refuge in Skull Cave itself, the perilous den of the Skullasaurus. Though very much afraid, the five all split up to search for Christopher Robin on their own; however, the Skullasaurus' roars and growls eventually bring Piglet, Tigger, Rabbit and Eeyore back together, who, mistaking Pooh's monstrously distorted reflection in a huge crystal to be the Skullasaurus, flee without Pooh. The bear becomes stuck in a narrow crevasse in the cave's crystals, and his muffled cries make the other four believe he has been killed and eaten by the Skullasaurus. Seeing the entrance to the "Eye of the Skull", where Christopher Robin supposedly is, the remaining four decide to push on for Pooh's memory, and are able to prove their potential: Rabbit proves his intelligence by devising a brilliant plan to reach the top, Tigger proves his strength by bouncing up there unassisted, and Piglet proves his bravery by getting Rabbit and Eeyore a way up to the ledge. Pooh has been watching this the whole time, and excitedly frees himself, only to hit a rock wall and descend into a deep pit, with no way out. While in despair at his permanent imprisonment, Pooh deduces that Christopher Robin is still with him in his heart, and it is enough to get the bear out of his sadness.
The others reach the Eye of the Skull, and indeed find Christopher Robin alive and well, but explain that Pooh was seemingly killed by the Skullasaurus. Upon hearing the creature's roars again, Christopher Robin explains that they are only the growls of Pooh's stomach (Pooh had never eaten any of his honey because he had intended on saving it for when he found Christopher Robin), and explains he had to go to school not Skull, and he would return in the afternoon. Rabbit, to his annoyance, realizes that Owl misinterpreted the message. Christopher Robin soon rescues Pooh from the deep pit, much to the bear's joy.
The six exit Skull Cave, only to discover that from the outside, it is far less frightening then when they first arrived. Christopher Robin explains that since they were alone and afraid, it only appeared to be huge and menacing, and this proves true for all the obstacles they'd faced on their journey as they happily march home. That evening, Christopher Robin says he will still have to return to school, but that they have no need to embark on another quest to find him, since he will always return. Pooh declares that he will always be waiting for him, and the two happily watch the sunset, knowing they will always have each other in the sanctuary of the Hundred Acre Wood.
- "Forever & Ever", Performed by Jim Cummings and Frankie J. Galasso
- "Adventure is a Wonderful Thing", Performed by Andre Stojka
- "If It Says So", Performed by Ken Sansom
- "Wherever You Are", Performed by Jim Cummings
- "Everything is Right", Performed by Jim Cummings, Steve Schatzberg, Dylan Watson, Ken Sansom and Frankie J. Galasso.
- "Wherever You Are" [Reprise] (End Title) Performed by Barry Coffing and Vonda Shepard
Pooh's Grand Adventure has garnered much less praise than its predecessors. It has received generally mixed to negative reviews from critics. A common criticism for the film was it its unwelcome introduction of maturity and dark imagery for a Pooh film. The review aggregator website Rotten Tomatoes reports that 38% of the critics gave the film a positive review based on 8 reviews, making it unique in that it became the first and only Pooh film to earn a "rotten" certification, and also the only direct-to-video Pooh film to have a score at all. George Blooston of Entertainment Weekly gave the film a C grade, calling it "treacly" and criticized its lack of "grown up-wit [and] child psychology of the four A.A. Milne stories Disney adapted so long ago." Reviewer Ellen Rosen felt that its story was "meaningless" and that "eighty percent of it's scenes are scary." David Nusair of Reel Film Reviews called the film "tedious", and Alex Sandell of Juicy Cerebellum felt that Disney "sucked with [it]."
Not all reviews were negative. Jane Louise Boursaw of Kaboose gave the film a mostly positive review, praising the songwriting and script. John J. Puccio of Movie Metropolis was also positive; while he admitted that it's more "adventurous" than Milne's stories, he felt that this was compensated by "unaffected charm" and visual appearance. Maria Llull of Common Sense Media did not think there was much violence, giving it three out of five stars and saying that it was okay for kids three and up, although this led to criticism from adult users on the site who criticized her for underrating the film's content.
- Kanga, Roo, and Gopher are absent in this film.
- Frank Welker was originally going to voice the Skullasaurus growls, but was later replaced by Jim Cummings, who also voiced Pooh and provided Tigger's singing voice.
- This is the first time Brady Bluhm voiced Christopher Robin and the first time Andre Stojka voiced Owl.
- This was the last Winnie the Pooh film in which Paul Winchell voiced Tigger. However, it wasn't the last time he voiced him. His last time was in Winnie The Pooh: A Valentine For You. He was originally supposed to voice Tigger again in The Tigger Movie in 2000, but his voice had become somewhat scratchy by the recording date, so he was replaced by Jim Cummings, the voice of Pooh and has remained his actor ever since.
- Parts of the plot of this movie (namely the presence of Skull, along with other aspects) were adapted for the 100 Acre Wood world in Kingdom Hearts II.
- This film has 2 remixes by Pogo in 2011.
- Even though the original 1997 videocassette of Pooh's Grand Adventure was not part of the Walt Disney Masterpiece Collection, the video does contain the collection's logo at the start of the film as a mistake.
- When the film was released on Blu-ray as a 20th Anniversary Edition, the box art had a cropped version of a poster from the 2011 Winnie the Pooh film.
- Christopher Robin's line "You are braver than you believe, stronger than your seem, and smarter than you think" is recited by Cyrus Goodman in the final episode of Andi Mack.
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