I remember what game you're talking about, but not the name. your character wore some goofy hat and sweatshirt with a really high collar and glasses... I think. Anyway, he was featured in a series of games, I can remember playing one wher you went around gathering these parts for a car and then racing it.
The one thing that sticks out for me about the game you mentioned was this little cave you had that you stored all the items you won in. Everytime you'd scale the mountian, you'd get to the top and they'd give you some stupid little item and you'd drop back down to the bottom to do it all over again. I can recall two of the games they had you play, one was with weights and a balance, and the other was where you went into this dark cave and these little glowy gems would appear and you'd have to count them within a time limit. Of course, too many would appear at once and you'd have to revert to multiplication.
If it helps (and if we're talking about the same game), I think I played it on the Mac. Not to say that it wasn't on the PC, but when I was in grade and middle school, they had nothing but Macs.