From that picture? The answer is: none of them, really. A few that have died that really bummed me out were Adam "MCA" Yauch, Ronnie James Dio, and, especially, Robert Heaton of New Model Army. That one still makes me sad some ten years after his death.
elliott smith, although it wasn't a surprise. nick drake and sandy denny as well... both deaths were quite sad.
Sinatra. Usually celebrity deaths don't affect me... But when that news spread, I just went into a room, played some Sinatra, and soon tears came out.
Roy Orbison. I was just discovering the depth of his music and had hoped to see him live the next time he toured.
Terry Kath (1946-1978) - Chicago's original guitarist and vocalist His virtuosic guitar playing has put Chicago in the rock map. Terry Kath on lead guitar and background vocal, Peter Cetera on lead vocals and bass.
At this moment that would be Johnny Winter. His first Columbia album "Johnny Winter" has been an immeasurable inspiration for me. The other artists I miss the most: Frank Zappa Sandy Denny Don Van Vliet Judee Sill
Loosing Miles in '91 hit me pretty hard, and I remember tearing up when I finally saw the footage of the Miles and Quincy Jones concert where Miles revisited the Gil Evans charts. George Harrison and Rick Wright were a couple others that hit me harder than I'd expeceted. Joe Henderson, Andrew Hill, and Sam Rivers too - we're also big losses, though perhaps not as unexpected at the time.
In that picture? George Harrison for sure. It came on the radio as my alarm was going off that morning in 2001. I went to an Umphrey's McGee concert that night and they did a bunch of musical tributes to him in their set. Biggest though was definitely Jerry Garcia. There are times when it can still bring a tear to me eye. I went home "sick" from work as soon as I heard the news.
I'd have to say Karen Carpenter. It was such a shock. It didn't seem to be a massive press story either. Very much a two day wonder.
I resented and lamented the breakup of my favourite band, in September 2011, and I believe a disbandment is similar to a death because a living entity ceases to exist, even if individual members start new projects it's never the same.
Based on my wild guess of what great music might have been created if the artist had not died at such an early age: Buddy Holly
I lost three heroes in the 90's (Miles, Zappa, Garcia) but Lennon is still the one that makes me feel most angry and sad.