In 1993 I caught my sister convincing my parents to purchase Oregon Trail at the Fairbanks Fred Meyer. Requiring parity, X-Wing, a Star Wars space combat simulator, made it onto the conveyor belt. But that's not what this story is about.
Everyone in my household eventually dabbled with Oregon Trail. The over sized box was torn apart and the discs within were inserted successively into the old Gateway machine that replaced an aging Apple product. After my sister had her fun, I commenced with playing the shit out of it - and left a trail of bodies in my wake. As the game became too easy - repeated expeditions fine tuned to maximize survival - I intentionally ramped up the difficulty with my own cruel rules.
Only the strong survived. Disease and "food" was the Darwinian method for parsing out the weak and feeble. The Trail was the great judicator.
I think I quit playing when I completed my ultimate goal - survive to Oregon sans a family. So many times my parasitic wife or children would survive cholera and starvation, reaching the promised land a shell of who they once were, but alive. Those fruits of the west coast were to be mine alone.
However the best part - and main catalyst for remembering all of this - is that my mother would also play. The game stored information beyond high score. When your quest failed (as mine so often did, under such despicable conditions), the game left a headstone where you finally capitulated. Mommy stumbled upon the fabled Butthead Expedition, and Butthead's tombstone. She was at first appalled the developers had such crude tastes at world buiding, and then laughed after unearthing the true nature of my game play.
Edit: starvation.