- Jon "Don Jon" Martello, Jr. as Christopher Robin
- Barbara Sugarman as Darby
- Esther as Kanga
- Bobby as Winnie the Pooh
- Angela Martello as Kessie
- Monica Martello as Porcupine
- Jon Martello, Sr. as Roo
- Danny as Tigger
- Priest as Piglet
- Emily Blunt as Mama Heffalump (cameo)
- Anne Hathaway as Holly (cameo)
- Cuba Gooding, Jr. as Rabbit (cameo)
- and more
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