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Winnie the Pooh: Sing a Song with Pooh Bear is a Winnie the Pooh-themed sing-along video, later rereleased as a Disney Sing-Along Songs entry. It generally revolves around Pooh trying to find his own song and visits each of his friends and listens to theirs for inspiration.

Was later re-released in 2003 as Sing a Song with Pooh Bear & Piglet Too!, with some extra songs from Piglet's Big Movie added on.

Featured songs:

  1. "Winnie the Pooh" (The Many Adventures of Winnie the Pooh) note 
  2. "Rumbly in My Tumbly" (Winnie the Pooh and the Honey Tree)
  3. "The Wonderful Thing About Tiggers" (Winnie the Pooh and Tigger Too)
  4. "Kanga Roo Hop"
  5. "Try a Little Something New"/"High and Low" (Welcome to Pooh Corner)
  6. "With a Few Good Friends" (Piglet's Big Movie) note 
  7. "You're the One and Only One" (Welcome to Pooh Corner)
  8. "The Floating Song" (The New Adventures of Winnie the Pooh)
  9. "Harvest What You Grow"
  10. "Heffalumps and Woozles" (Winnie the Pooh and the Blustery Day)
  11. "Nothing's Too Good for a Friend (The New Adventures of Winnie the Pooh)
  12. "Sing-Ho (For the Life of a Bear)" (Piglet's Big Movie) note 
  13. "My Song"

This video series contains examples of:

  • Animation Bump: "Kanga Roo Hop" and "My Song" have newly animated music videos compared to the Stock Footage making up the rest of the film. The former was likely a necessity as Kanga and Roo hadn't appeared enough to paste together a music video by this point.
  • Flashback with the Other Darrin: Averted. All the recycled tunes with Tigger still use Paul Winchell's original vocals, despite Jim Cummings voicing him for the rest of the feature.
  • It Was with You All Along: In the end, Pooh discovers he has had his own song with him the whole time, and didn't even realize it.
  • Mythology Gag: It features tunes not just from The Many Adventures of Winnie the Pooh, but also The New Adventures of Winnie the Pooh and even Welcome to Pooh Corner.
  • Stock Footage: The large majority of the film is recycled footage from Many Adventures, New Adventures, and the movie, Pooh's Grand Adventure with the "Winnie the Pooh" song in the original VHS release being reused from Disney's Sing Along Songs: The Bare Necessities.

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