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In the beginning, we see Tigger, Pooh and Piglet escaping prison, jumping into Christopher Robin and his train. They then head for a dead end and the dream ends where Christopher Robin's toy train falls down the stairs. A babysitter watching Christopher Robin while his mother is out sends Christopher back to bed. However, Christopher is not sleepy, ands makes four messes and the babysitter, not to mention Christopher's mother, gets mad. Thinking that babysitting is the easiest job, Christopher Robin, Pooh, Piglet, and Tigger try to watch Roo while Kanga's out, and finds out babysitting is harder than it looks. Roo is eventually found after the gang loses him, and Christopher Robin listens to his babysitter the next time he is sent to bed, as do Pooh, Piglet and Tigger. When Christopher Robin's babysitter checks on him, she feels proud.
|Jim Cummings||Winnie the Pooh|
|Tim Hoskins||Christopher Robin|
|Patricia Parris||Kanga and Christopher Robin's Mom|
|Jackie Gonneau||The Babysitter|
- Like Christopher Robin's mom, the babysitter's face is never shown, and is usually only seen from the neck down.
- When Christopher Robin accidentally switches on the vacuum cleaner, if you look real closely, the vacuum's nozzle is slightly anthropomorphized when it sucks up Pooh, when Tigger accidentally throws it in reverse, and when Christopher finally unplugs it before it reverts to its inanimate state.