I honestly did not get into pc gaming till about 2001 or 2002. First PC games I ever played were Sim City 2000, Nox (awesome game that I still play), Unreal Tournament, and Blood II: The Chosen (yet another game I still play from time to time.
Oh boy, I remember playing SimCity 2K after school. It's rough by today's standard, but it did make you feel like you were making your own city. I think it was the great terrain generator. It made every city look different and also added some limitations on how you could build your city.