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William Frawley. I'd been watching I Love Lucy since I was at least 2. Years later, I was told the Fred Mertz actor had died a long time ago. I found that traumatizing at 7 or 8 years old.

Then I received the bad news about Lucy and Rick's real divorce. Again, my world was shattered.

Within the last 10 years, probably Robin Williams, Lisa Marie Presley, & Kirstie Alley.

Biggest shock was John Lennon.

Princess Diana - definitely most shocking ever.
Ayrton Senna
John Lennon
Robin Williams

Glenn Frey's death really affected me because I was a huge Eagles' fan growing up and I tried to play all their songs on the guitar when I first started learning back in high school and also college. My family and I were actually on vacation in Florida when I heard the news. By a lot of accounts, he was a real jerk at times...but he sure was a talented jerk. He was a great singer, songwriter, and guitar player.

The biggest of my lifetime, though, has to be Elvis Presley. I can still remember the hometown newspaper headline on the front page: "ELVIS: DEAD AT 42." That was back in the day when entertainment rarely made the front page. His death was just such a huge news story.

Robin Williams genuinely made me sad.

Also, Chadwick Boseman. That one legit caught me off guard

Norm Macdonald.

Usually someone is depressed, on medication or a junkie and it's not totally unexpected but his was sad.

Princess Diana.

Santa Claus. and what was worse, found out at the same time that he'd never existed in the first place.

JFK
MLK
RFK