Who fits in this category?

I'm glad I'm not the only one who enjoys those characters for that reason. Watching them crack and piece themselves back together is awesome

Be careful... there are monsters here.

...doki doki literature club, oh god

*cough* Shallan Davar *cough*

I like that too.

Me too.

Stiles From teen wolf

Ray Palmer. Like, twice.

Barney Stinson?

But be careful not to piss those kind of people off, they can turn into absolute demons when pushed too far. I should know I'm one of them.

Watching their souls crumble inside their eyes is always fun!

Don't really want to be that guy but.... Sans?
Anyone agree?

LANCE MCCLAIN

Hodor ;;

I know it's a necropost but I'm on a random binge.
For anyone still following this there exists a named trope of this. Breaking the Cutie
https://tvtropes.org/pmwiki/pmwiki.php/Main/BreakTheCutie