I have games and at least one system from every era from NES-PS2. I don't really know what the oldest game in my collection is, although if re-releases count it's probably either something from this Forgotten Realms PC game collection I got back when the $10 jewel cases at Walmart actually had decent games in them, or my TV Play Power Intellivision thing (It's an Intellivision controller that has some games programmed in, and connects to a tv).