Sundog: Frozen Legacy (en.m.wikipedia.org/wiki/SunDog:_Frozen_Legacy) originally for Apple II but brought to PC. My friend and I spent countless hours roleplaying as Han Solo, trading contraband and pulling bounties. If you want an incredible space trading/combat sim experience, forget Star Citizen, this game is for you!
What is an obscure piece of media or videogame that you think nobody else here has heard of? (kbin.social)
It could even be a youtube video or movie that you don't think anyone reading this has heard of besides you.