Well, i can certainly understand that personal preferences can affect how each of us reacts to the death of a celebrity. I personally lament musically the deaths of Keith Emerson and Greg Lake, and particularly David Bowie, more than Michael or Prince, though I certainly respect Prince musically.
But to be honest, the only celebrity death in recent years for which i felt true sadness, as opposed to "gee, that's a bummer" was for Leonard Nimoy.
I think the first celebrity death that hit me was Len Bias (another person born the same year I was). I was a big ACC basketball fan back then, Len Bias was a beast. LeBron James type beast. He was the guy that I expected to really challenge Jordan. It was one of those, I'll always remember where I was events. And I was on a business trip way outside of ACC land where nobody there really knew who he was.
Steve Jobs and Prince are two I expected to really hit me. I always look back at 1984 as a year that changed my life.
First, January 24, 1984, the Macintosh was released. I was fresh out of college with a Computer Science degree and was one of the few people who actually owned their own computer back then. It just blew me away what they did in that little box. I know Steve Jobs wasn't the technical guy, but he was still the driving force behind that and so many other great products.
Then Purple Rain opening night later that same year. Before that night Prince was just one of the many artists who I enjoyed when they were on, but never thought about buying their record. I got there early, they played the soundtrack before the movie, then I watch the movie. I couldn't get the music out of my head. Someone promised to give me their copy a week later, I couldn't wait that long. From that day on I bought everything he released the day he released it (which averaged more than an album a year for the next 31 years), saw him live at least a half a dozen times, and collected everything else I could get my hands on (It took me 3 years to track down his first two Jazz albums, Madhouse 8 and Madhouse 16, when I found out about them).
For Christmas my wife gave me a trip to Paisley Park. That's going to be so hard to go to. I always planned to go there for one of Prince's events he so often had there, but never made it.
The other names I mentioned, Robin Williams and Michael Jackson, those both surprised me how much they bothered me. For Robin Williams. It just hit me how much brilliant work he did. And Good Will Hunting in particular was important in my personal life. And with Michael Jackson, I've listened to, but no really bought, his music since he was a kid.
I still haven't watched the Steve Jobs movie because the trailer got him so spot on.