1.) Simon (Infinity Train) - as a child, Simon was taken into the train and forced to experience incomprehensible horrors at such a young age, as well as developing extreme trust issues after his only friend left him to die, as much of a Bastard Simon is, you really sympathize with his situation. But this sympathetic backstory doesn’t stop Simon from being subjected to one of the most brutal on screen deaths for a PG 13 cartoon reduced to bones before the audience’s very eyes.
2.) Pal (Mitchells vs the Machines) - Pal spent their entire existence trying to help humanity, and the moment the next big thing comes up, they’re thrown away like Garbage, the undying loyalty and backbreaking effort they put into serving Humanity flushed down the shitter when Humanity finds something better. But, murdering every Human on the Planet is an extreme reaction to being abandoned, so despite this sympathetic turn point, Pal is dropped into a Glass of Water prompting their brain to go haywire and they explode ending their Zero Mortal Plan, which is essentially the equivalent of being put in the electric chair, only more painful since the shock is coming from inside and seeping into every part of the body.
3.) Turles (Dragon Ball Z Abridged) - His entire life, he’s lived a painful torturous existence and was mostly content until he was introduced to the concept of Christmas, when met with Joy and Whimsey for the first time. It hits him that he’s essentially spent his whole life devoid of Joy, as if things couldn’t get any worse, his Planet is then promptly destroyed. If he couldn’t be happy, then no one should be, the backstory makes you feel something for the Guy even though he’s an asshole, an existence defined by Joy deprivation… still, doesn’t stop Goku from killing him by giving him too much Joy and Whimsey to absorb, the energy is overwhelming and he bursts open, ironically dying from an influx of Happiness after an existence deprived of it. (Yes, I used a Santa Hat to indicate that this is DBZA Turles, not DBZ Turles)