Oregon Trail For sure... My brother and I always used to role play. For some reason I always died... jerk...
Sim town- Sim city sorta, but a lot easier and a lot more fun
Then there was this mother goose one where you had to go around and put all the nursery stories back in order (since everything was all mixed up)
Peg Leg For Kids- it was a never ending rocket ship game where all you had to do was shoot different objects in space. AWESOME!!!! can't find it anywhere though.
The fisher price games on the computer, Western, Castle, Pirate adventures.
Backyard Football. the one with john elway as a kid. Always used him as my quarter back.
Those are the ones from my youth that I really remember well. All the other ones I played were good, but those I spent so much time on! I never beat the mother goose one... very sad.... and now I can't find it