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The only educational game that I know with two hosts, one of which is a jack-in-the-box, is Alphabet Blocks. https://www.youtube.com/watch?v=fCOQJGCLYbY
Sadly that's not it, it was aimed at an older audience. I think more 7-8ish. It's also not 'Ready, Set, Read with Bananas and Jack', which is by the same developer and /is/ aimed at an older audience, but still isn't what I'm looking for.
If it helps, the screenshots I found of 'Ready, Set, Read' helped me remember something else about the game though. The hosts stand at the top of a staircase, on on the left and one on the right.
Edited by flamyangelwings I'd tell you about myself but then I'd have to, well, not kill you, but you'd end up on an island, exactly 140/260 Latitude 10/260 Longitude
Okay, so super vague here, possibly CD, possibly floppy disk. Game my older sister used to play in the late 90s. I swear it was Educational. One of the hosts was definitely a Jack-in-the-box, and I think the other was a teddy bear.
This is all I remember.