Pooh's Grand Adventure: The Search for Christopher Robin (also known as Winnie the Pooh's Most Grand Adventure in some countries) is a 1997 animated direct-to-video film directed by Karl Geurs. The film follows Pooh and his friends on a journey to find and rescue their friend Christopher Robin from the "Skull". Along the way, the group confront their own insecurities throughout the search, facing and conquering them in a series of events where they're forced to act beyond their own known limits, thus discovering their true potential. Unlike the film's predecessors, this film is an entirely original story, not based on any of A. A. Milne's Pooh stories (although some elements derive from In Which Rabbit Has a Busy Day and We Learn What Christopher Robin Does in the Mornings from The House at Pooh Corner).
The film was the first Winnie the Pooh feature film to be released direct-to-video. It received mixed reviews from critics due to its dark themes and imagery. However, it is also the first Winnie the Pooh film ever to have its own special edition.
The film's plot is based primarily on all two A. A. Milne stories from The House at Pooh Corner: "In which Rabbit Has a Busy Day and We Learn What Christopher Robin Does in the Mornings, and "In which Christopher Robin and Pooh Come to an Enchanted Place and We Leave Them There".
The story begins on the last day of summer. Christopher Robin is unable to tell his friend Winnie-the-Pooh that he must begin going to school, and leaves him with the advice, "You're braver than you believe, and 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. He goes around to his friends Piglet, Tigger, Rabbit and Eeyore, and none of them are able to read it, so they ask Owl for help. From misinterpreting the note, Owl deduces that Christopher Robin has been taken to a distant, mysterious and dangerous land called the "Skull" against his will, by a ferocious beast who dwells in it, the "Skullasaurus". Owl equips the group with a map and sends them into the "Great Unknown" of the Hundred Acre Wood, warning them of the Skullasaurus.
During their travels the group slowly realizes just how helpless they are without Christopher Robin in the outside world. Piglet, Tigger, and Rabbit come to believe they don't have the courage, strength, or intelligence respectively to go on; Piglet is abducted by a swarm of butterflies in a tranquil field, leaving him feeling weak and helpless; Tigger plummets into a large ravine and becomes saddened when he is unable to bounce out to safety, causing his friends to fall with him, and Rabbit manages to get the group lost in the fog, admitting that "he hadn't known for hours" where they were going. Pooh tries to comfort them each with the advice Christopher Robin had given him, but fails due to his inability to remember exactly what he said. The group comes to terms with the fact that they are lost and helpless without Christopher Robin, and take shelter in a nearby cave. While everyone is asleep, Pooh laments getting no closer to finding Christopher Robin.
In the morning, the five realize they'd spent the night in the "Skull Cave", where Christopher Robin is supposedly trapped. The five split up to search for Christopher Robin on their own. Pooh gets stuck in a small gap in the cave's crystals, and the four others tumble about before finding the "Eye of the Skull" where Christopher Robin is. They demonstrate their courage, strength, and intelligence to reach the eye (Rabbit thinks up a plan to reach the "eye", Tigger bounces Piglet up to a ledge, and Piglet faces his fear of heights to toss a rope down to the others). Upon seeing his friends' bravery, Pooh excitedly frees himself from the crevasse, only to hit a rock wall and slide down into a deep pit, with no way out. While there, he realizes that Christopher Robin is still in his heart, even when they are not together, just as Christopher had promised. After Piglet, Rabbit, Tigger and Eeyore make their way up to the eye, they find Christopher Robin alive and well. He explains he was at school, and that the Skullasaurus is actually Pooh's growling stomach.
Christopher Robin then rescues Pooh from the deep pit with a large honey pot. The six exit the Skull Cave, only to discover that from the outside, it and all the other locations on the map weren't nearly as big, nor as scary as they seemed. They return home, and that evening, Christopher Robin says he will return to school the next day. 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 and 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, Dylan Watson, Ken Sansom, Steve Schatzberg, Andre Stojka, and Frankie J. Galasso.
- "Wherever You Are" [Reprise] (End Title) Performed by Barry Coffing and Vonda Shepard
- Jim Cummings - Winnie-the-Pooh/Skull
- John Fiedler - Piglet
- Steve Schatzberg - Piglet (singing voice)
- Ken Sansom - Rabbit
- Paul Winchell - Tigger
- Peter Cullen - Eeyore
- Brady Bluhm - Christopher Robin
- Frankie J. Galasso - Christopher Robin (singing voice)
- Andre Stojka - Owl
- David Warner - Narrator