As in, what living celebrity death will make you mourn the most?
For years, Roger Ebert would have been my answer, but this has now occurred and I have both mourned and moved on. I still think of Ebert when I see a great movie and on some level, even more when I see a terrible one. I miss his reviews, his tweets, and his blog entries.
Anyway, I think Werner Herzog will sadden me the most. Is there a better director in film history? But aside from that, is there a more interesting person working today? I’ve seen countless of his movies and have so much admiration for him as an artist, I will miss his presence on this Earth greatly.
When he dies, I will watch:
Grizzly Man
Fitzcarraldo
Bad Lieutenant
Aguirre
Rescue Dawn
Little Dieter
Wings of Hope - find it on Youtube!
And many others. I want him to live to 110 years old.
Who will you miss the most?
William Shatner will hit me hard. So will author Valerie Martin. Pat Conroy too. Jimmy Carter. Jesse Jackson.
David Bowie. How can there be a world without him in it 
Clint Eastwood and Bob Dylan will both be massive losses for me. So will Paul McCartney, although I fully expect him to live forever. 
All of the surviving TOS cast, but Shatner in particular.
Joni Mitchell, first and most. Bob Dylan and Leonard Cohen, too.
Mostly musicians. Dylan and Cohen as already mentioned, plus Bruce Springsteen, Neil Young, Willie Nelson, Phil Lesh… I’m sure there’s many more, but all of them are over 65 now and still making great music.
Terry Pratchett already did. Most celebrities are just people to me, but I had met Pterry on several occasions, and he was more than just an author to me.
I agree with Cinnamon Imp. I still remember the day, at age 7, being introduced to the music of David Bowie, then my jaw dropping in awe upon seeing a picture of Ziggy Stardust for the first time.
He’s been my biggest musical influence and many of his songs take me back to significant moments in my life.
I will mourn his death if he dies before me. I will also be exceptionally sad when all the Beatles have gone.
And Bryan Ferry too.
Two from the past:
Robin Williams. I liked him a lot as a comedian and actor and his out of the blue suicide struck me pretty hard and stayed with me for awhile. Later, we learned what he was facing and I could understand better his mindset, but it just didn’t make sense at the time
Whitney Houston. She was a year younger than me and one of my favorite singers for a long time. I remember when she first started on the national scene in 1985. I thought she was on the upswing with her comeback, but I could tell there was trouble, with the rumors of a relapse and her voice problems. Still, her death struck me hard
Davids Bowie and Attenborough.
Terry Pratchett used to pretty much be at the top of the list. Paul McCartney and Bob Dylan, too. Leonard Cohen might make me a bit sad. Beyond them, everyone else can pretty much just kick the bucket whenever they want.
Already happened–John Denver. I grew up listening to his music, going to his concerts and learning to play the guitar to his tunes. His death just wrecked me.
Bobby Darin. I knew he’d had a recording career, but the summer before he died, he had a rather successful summer replacement TV show. Really good, I loved it. Then, gone.
When Jim Stafford passes on, I will be extremely sad. A world without that sense of humor not floating around out there somewhere? No, thanks.
I’ve been working my way through a lot of 1960s era Doctor Who, and was simultaneously both a)surprised to learn that William Russell (Ian Chesterton) was still alive and b) struck by how devistated I’d be when he died. But really anyone in the Doctor Who universe dying would make me quite sad.
Thirded for Pratchett. I never understood before then why people could be so affected by the death of, to them, a near perfect stranger. Now, I have some idea. Unlike Silenus I’ve never been even in the same room as Sir Pratchett, nor sent so much as a fan letter. But every time I read one of his books I feel as if I’m having a conversation, albeit a very one sided one. Now the conversation is over.
C’est la vie, c’est la mort. Time to move on.
We did this last year and here is my response.
Sadly, I was correct about one of my choices.
Will affect you, folks. Will.
Terry Pratchett and Leonard Nimoy belong to the past, my friends. Tragic, same as Ebert. But who will affect you as much?
Robert Duvall for sure.
That one will really depress me.