I was bummed when Lou Reed died for about 4 days. Kurt Cobain was a hard one for me as well. I heard the news that a dead body was discovered at his property on my car radio on a lunch break and I knew it was him.
Most celebrities I can't find any reason to feel any connection with that would make their death extremely sad to me personally.
I don't understand the spectacles of public grief that surrounded the deaths of Elvis, Kurt Cobain, and John Lennon, and Princess Diana.
Or JFK. His death has been depicted over and over in history and movies as a national trauma.
Most people I know that remember that that were around I doubt were breaking down crying about it. Probably just shocked and glued to their TV's like I was when Reagan got shot.