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Are you referring to Michael K. Williams or Cindy Williams?

John Ritter.

Kurt Cobain and River Phoenix were both big shocks. They were close to my age. I knew Cobain had issues with mental health. He even did a song called "I Hate Myself and Want to Die". Suicide is a pretty drastic action, though. He had a lot of things going for him too, obviously.

I didn't know about Phoenix's drug problem so when he died outside a nightclub of an overdose I was blindsided. A great young actor suddenly gone.

tookie williams?

Phil Hartman was the all time worst and most shocking for me.

Yeah, Robin Williams' death was terribly sad, I had no idea the guy was depressed, he seemed like the life of the party, but maybe his manic comedic style was a mask to hide whatever he was dealing with..?

For me, Tom Petty.
I always figured he messed around with drugs, a lot of the music stars do but that chemical pill stuff is just awful trash for you.
What a waste of a great rock talent. He seemed really too 'Zen' and defiant to ingest that shit.

Whitney and Prince kicked me in the head a bit too, what music might they have been doing now, probably legendary stuff.

The '27 Club...'
It was before my time so it was no shock but what a supreme waste of amazing skills. I've read about Hendrix, Janice and Morrison... terrible waste of talent.

When David Bowie died in 2016 it affected me more than usual. The whole rest of the day didn't feel right.
When I found Michael Nesmith from the Monkees died it also shocked me as I was a huge fan when younger.
The suicide of designer Kate Spade still haunts me sometimes.
The death of Michael Jackson in 2009 didn't really shock me but that whole day is one of the most vivid memories I have. A major "where were you when you found out..." moment.

Brittany Murphy
Robin Williams
Prince