- Winnie the Pooh fills in as Captain Willard, with a voiceover from Martin Sheen, the original actor. He is sent on a military mission to kill Kurtz/Eeyore, taken from his abode where he withers away.
- Eeyore is presented as the voiceover for Kurtz, visually portrayed as Marlon Brando, a rogue soldier whom Pooh is sent to kill.
- Gopher is featured as Lt. Kilgore, with a voiceover from Robert Duvall, the original actor. He is a soldier Pooh and his company encounter on the hunt for Kurtz/Eeyore.
- Rabbit, Christopher Robin, Roo and Owl are presented as Chef, Lance, Mr. Clean and Chief respectively. They are the crew sent to escort Pooh on his mission.
- Piglet is presented as an American photojournalist, with voiceover from Dennis Hopper, the original actor. He worships Kurtz/Eeyore.
- Tigger is presented as a tiger in the Cambodian jungle. Pooh and Rabbit encounter him at one point.
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