I think this might be an interesting topic to see if any gems come out of the woodwork.
If I may I will start it off.
My wife, Dorothy and I were both born and went to school in Sunderland, UK. My nomination is Dave Stewart of the Eurythmics and a number of other bands. As it turns all three of us are about the same age, Dave Stewart although not born in Sunderland, went to school there, as he moved from Glasgow when he was quite young.
Before I met her, my wife used to go to watch him play at the local folk clubs in the late 60’s early 70’s when he was around 18, she says he was very good and destined for greater things, the rest they say is history. My link to him is that Kai Olsson (yes his brother was Nigel Olsson, Elton John’s drummer) was in my class at school. He and his friend who sat behind me spent all their time writing lyrics. Kai joined Dave in I think their first band Longdancer and they had some success. Kai went on to have a career as a guitar player, releasing albums but not reaching the heights as Dave Stewart.
When I was in college, Tracy Chapman was roommates with a friend of mine. I met her, and we would see her play at the college pub for a dollar. I never hung out or became friends with her, though. She was great to see play at that stage.
Also in college, my freshman year, I lived upstairs from Neil Diamond’s daughter. We did get to show Niel Diamond what “Hacky Sack” was. He was already famous of course. I like to joke that my claim to fame was that I taught Niel Diamond how to play Hacky Sack, but it really wasn’t more than him asking what we were doing when his daughter came by and introduced him to us briefly.