10 Anime Fates Worse Than Death
1. Being Consumed By A Parasitic Tree - Yu Yu Hakusho
As the leader of the Apparition Gang and one of the show's longest-running antagonists, Elder Toguro was a major thorn in the side of the leads. Therefore, it was inevitable his eventual demise would need to be epic, and that it certainly was.
The older Toguro brother was one nasty piece of work, as this former human turned demon had an unhealthy relationship with cruelty and violence. He would kill mercilessly and even joke at the expense of those he defeated, which led to plenty of conflict for him, even with his own brother. This was all made worse as his regeneration powers could essentially bring him back from the brink of death.
After managing to take over the body of physic Gourmet with his shapeshifting/regeneration powers, Toguro engaged in a fight with Kumara. However, during their encounter, Kurama planted the seed of The Sinning Tree in him, which ensnared the awful demon in a perpetual state of torture as he hallucinated a losing fight against him forever.
Typically, the tree would work until its host died, but as Toguro could regenerate, he became locked in an eternal hell. Kurama hit the nail on the head when he said, "rogues like you deserve to be damned", and this is as close as you can get.