He was born in the early 20's, served in the U.S. Navy during the Korean War. Has been middle class in the Northwest his entire life. What do I ask to get a glimpse at the eras he got to see? What questions could give me an insight into the economic, social and political changes he has witnessed?
I am in my early 20's, my grandpa died when I was young. Didn't get the chance to learn much from his history. I don't want to let this opportunity go, but I am not well-versed in 20th century history.
Essentially, what can I ask that would be personable and historically enlightening? I want to capture how his perspective as a young 20 yearold must have been radically different (yet similar in perhaps some ways) to how I live today.
Think about all of your major moments in life so far first. What was school like, college, dating, marriage, etc. Major events like the Great Depression, WWII, Kennedy assassination, and all of the different wars. When did his family get a car, a tv, a microwave? My favorite thing to learn about was their opinions about their older relatives. What was his relationship with his Grandparents? Family stories often get forgotten because we only ask about their life rather than what stories they were told.
If you would like to see or hear a number of really good oral histories, visit studsterkel.org to find examples. Studs Terkel is considered one of the greatest American oral historians and his interview subjects come from a diverse background. There are also many books written on the subject, but most are found in university libraries as opposed to local county or city libraries.
Not a historian here, someone who had a similar situation that didn't quite end as well as might be hoped.
My grandfather was born in 1928 (EDIT: numbers might not add up now that I think about it, maybe a bit earlier? I thought it was '28 though). Sometimes he would tell stories about his career, including his work at the White Sands missile range (or maybe it was "a missile range like White Sands", I can't really remember) - around the time of the Roswell incident, etc. He would say things about how irresponsible they were, just firing things everywhere, strapping on animals with little or no ethical oversight, things sometimes going a little off track into Mexico, etc. I have no idea how much he embellished the stories, but he was a pretty serious guy, and I'll bet a lot of what he said would've been of historical interest if we had only recorded it.
We kept saying that we would, but we never did. Then one day he died, and that was that.
OP, please, do more than just ask things, keep a detailed record! Could be a camera, an audio recording, a journal, anything. You never know what might come up.
Ask him about firsts.
The first car, the first television, the first airplane flight.
His own or his friends or the family down the block, doesn't matter.
My grandmother was born in 1906; on the day the first car came to town, the schoolmistress dismissed all the kids to run and see.
When her father bought one, she became the first person in the family to learn to drive at 15. He said she was the child of the new century, not, him, he'd stick to horses.
There's a really good resource on oral history interviews here.
I'd make sure to ask about family anecdotes. We have plenty of first hand accounts of personal lives from the 20th century. What we probably don't have are first hand accounts of your family history. Make sure you get that taken cared of first and knowledge of the particular time will flow from there.
/r/Genealogy will likely have good ideas and resources for what kinds of questions to ask and how to get the ball rolling for family related questions.