John F. Kennedy, Jr. I am only a few years older than he was (just about the same age as Caroline), old enough to remember him saluting his father at his funeral. His so pointless death hit me way harder than I expected it to.
In my time it seems like it’s always been guitar players. In the following order, notably: Randy Rhoads, Stevie Ray Vaughan, Jerry Garcia. There are a few more that should be on the horizon, but I’m not going to jinx them, life is short.
Celebrity death: Kirsty MacColl - so young, so full of life; it was so unexpected and meaningless and unfair. I still find it hard to take in.
Living celebrity: it will be some similar circumstance to the above, something full of shock
As for which affects me most - I’ll know when it happens.
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- Sir Terry Pratchett, before his time, and to dementia. He had so many more stories to tell. Another sad one was Jim Henson, who died because he didn’t want to bother anyone and let an infection go so long it was incurable.
- I’ve gotten so used to losing the greats that I don’t get too worked up anymore. Maybe someone like Greta Thunberg.
- Sir Terry
That was a weird one for me. I never thought much of him and rolled my eyes at the attention he got for his looks and because of the accomplishments of his family, but he was the speaker at my then girlfriend’s college graduation right before he died. I had a front row seat.
- Christopher Reeve
- William Shatner
- Christopher Reeve
Shatner has been part of my life longer than Reeve, as I was introduced to Star Trek sometime during or before the second grade, and Reeve’s Superman didn’t come out until I was in the fifth grade, but the circumstances of his accident and the nobility with which he lived the remainder of his life have placed Reeve into the category of people I admire most. If I were the kind of person who could unironically claim to have heroes, he would be one of them.
Right Freddie Prinze was a big one at the time.
- Robin Williams was the saddest. He was a big part of my youth (Mrs Doubtfire, Dead Poets Society) and the fact that he was lost to mental illness was just terrible.
Amy Winehouse was a big loss too, given her age. - I don’t want to jinx anyone, but losing someone young like Adele would be very sad.
- Hard to say
**John Belushi. **I was a huge fan, and at 18 it was the first time someone of whom I was a fan died before his time. I remember being sad to an extent, but mostly angry that I’d never get to see him in anything new ever again. That sounds selfish, but it’s how I felt at the time. I only learned later how addicted to drugs he really was, and I still sometimes think about what he could have done with his talent if he’d been able to clean up.
There’s no telling what current celebrity’s death will affect me. It would have to be somebody young who has much more to give to the world to hit me as hard as Belushi did.
Big plot point of the movie Fame in fact.
Stevie Ray. He was getting better every day. And I figured I’d always have a chance later to see him play.
If Dave Grohl bought the farm, I’d be sad. He’s a cool guy, with a mess of kids, and I haven’t seen him play yet, either.
If Prince were still alive, he’d be my #2, but not my #3.
The deaths that affected me the most were :
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John Lennon
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Stan Lee
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Charles Shulz (creator of "Peanuts)
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Teresa Graves (the star of the TV show “Get Christie Love”, from 1974-1975 ; I had a huge crush on her!)
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Fred Rogers
Living celebrities whose deaths will affect me :
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Paul McCartney
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Ringo Starr
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Barry Gibb
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Kate Jackson
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Lynda Carter
Oh, wow, I forgot these two, too. 
Afterthought: I’m gonna lose my sh!t if/when Garry Trudeau isn’t Doonesbury-ing any longer, whether that’s retirement or something more final.
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Jerry Garcia. I was completely useless for about 4-5 days after he died. Hit me like a ton of bricks.
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It’s really hard to say. If someone I really enjoy dies unexpectedly at a way too young age, it would probably be a bigger blow than someone who’s been around a while. For instance, if a car crash or some such thing killed off Stephen Colbert, it would rock me pretty hard, but when Willie Nelson’s time comes I’ll be deeply saddened by his loss but not devastated like that.
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I really don’t think another celebrity death will ever hit me like Garcia’s.
Terry Pratchett.
Not just for the loss of such a brilliant man.
But for the loss of an entire universe, with characters that I knew and deeply loved, which I could never visit again.
REALLY hit hard.
Janis Joplin
Cass Elliot
Leon Russell
Anthony Bourdain
Robert A Heinlein
I too was deeply affected when Terry Pratchett died. I cried for several days and if I think too long about it, I burst into tears still. And the weird thing about how much it affected me is that I haven’t been a fan for decades. Only about 6-7 years.
George Michael’s passing (which, coincidentally, I found out about while watching Hogfather to unwind from Christmas drama) also still bothers me a lot. I know he wasn’t as popular when he died as he was in the 80s and 90s, but I still listen to his music all the time.
I don’t want to think about the few celebrities’ deaths that would destroy me further. Or they might just bother me so much I shut down. Maybe George and Pterry hit that sweet spot between “oh that’s too bad” and “oh no I can’t process this. Let’s pretend it didn’t happen.”
Karen Carpenter. Amazing talent.
James Gandofini aka Tony Soprano