Damn. Hard call. There's only been a few that have hit me because I don't really have a parasocial connection to anyone to any degree worth mentioning.

That being said, the three that made me actually cry were Vonnegut, Kris Kristofferson, and Chester Bennington.

Chester, I was listening to the one more light album when I found out, so it hit extra hard.

Vonnegut though, he more than any other writer made me think and want to create with words. He shaped how I view literature and think about writing. So his death hit harder than most.

Kristofferson, it's that I had known it was coming. He'd already been lost to a great degree, but I had been low key dreading the news because he's so damn iconic. He's the kind of poet I wish I could be. And his music was also damn good lol. Also, he's symbolic of an era of music that's disappeared, and as the last of the highwaymen have died, with only one left there's this hole in the world that isn't likely to be filled now that the entire music industry has fallen into disarray. It's much harder for that kind of poet bard to exist and have their music spread now. In any genre, btw; the same difficulties exist in folk, metal, rap, etc.

Anyway, those are the ones that made me cry as a grown-ass man. I suspect I'll shed another tear when Willie goes, and I know I'm gonna fall apart a little when Dolly does. Luckily, the next wave of writers and musicians that I'd likely cry over are a good twenty years younger (or more) than them, so I'll have a break after that. Likely be dead myself before most of the others would go.