I have a Gravis Gamepad Pro gameport version and it is the cause of many problems for me under W2K (works fine in WinMe) - the only BSODs my W2K box has ever shown are from playing with this thing - ...
I remember Project64 used some weird system like combinations of keys to give different analog tilts, e.g. shift + left arrow might be 50% tilt. So that certainly didn't require an analog controller.