I can’t really contribute any new extremes to this thread, as I’m more than a generation younger than some of the posters. Heck, KlondikeGeoff is 78 years old and a doper? Go KlondikeGeoff!
But I do have a few “living memory” type stories. My paternal grandmother was the youngest of 11 or so children, and some of her older siblings survived until I was at least old enough to talk to and understand them. My (great-)aunt Mary, in particular, told the story of their emigration from Russia (Galitsia, near Kiev, I think). They were smuggled out of the village in a hay wagon, then walked a distance basically equivalent to the entire breadth of the continental US, got on a boat in Austria, got to Ellis Island, had one daughter temporarily removed because she needed to be deloused, and almost couldn’t find her when they came back because her hair had been shaved off.
On the other side, (and this is more for the interesting situations than the far-back-in-time-aspect), my maternal grandfather was a rocket scientist, and was involved in many aspects of the space race. In particular, he told me how he was present at the meeting where the IBM engineers told them about the first transistor computer (or maybe the first IC computer), which was 2/3 as powerful as the huge-ass-mainframe, but about the size of a breadbox. (The astronauts wanted a computer on the apollo flights to help navigate) (I think). Oh, and there’s a great photo of my maternal grandmother (still alive, although weakening at 91) playing in a string quartet with Einstein.