I think my parents generation, born just before and during WWII have had a pretty good run. They have lived during a period of generally increasing wealth, left school when you really could decide what you wanted to be, saw great cultural changes through the late 50’s and 60,s and are witnessing the huge changes brought about by IT developments, retired with final salary pension schemes and are growing old when medicine and medical care have made great advances since their birth, and before the NHS completely collapses under the weight of self inflicted illness.
I recently listened to a man describe how he had watched the moon landings with his grandmother who as a small child had survived an attack by native American Indians which had killed many of her family. That would have been an interesting life history.
For me it probably has to be ancient Rome, which I attribute to the wonderful writing of Robert Graves.