Osaka is a character from an anime called Azumanga Daioh, and her appearance here owes to this clip from a series called AMV Hell.
The premise of the photobook was to keep most of the original special's content, but make it seem new and interesting. The Dinah Shore "Twelve Days" was always in from day one, but who would perform it? It wasn't always Osaka--originally, it was Hello Kitty. The idea was that she was doing part of "Twelve Days" for the school Christmas show, but she was having trouble remembering under pressure. Her constant starting and stopping and restarting would have irritated Pee-Wee, prompting him to grab the decoy doll and duck out of the call. Problem: The idea of her finally twigging that he hasn't moved in a long time made Pee-Wee look mean-spirited, for Kitty is canonically five or so.
The change from Kitty to Osaka made the endeavor ten times funnier--she doesn't notice that Pee-Wee isn't moving, and she's obliviously carrying on regardless.
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