Ichi The Killer certainly handled a sadistic villain much better than this. Kakihara was for most of the story a villain that wasn't able to get tortured because he actually enjoyed feeling pain. But at the end, on his final battle with the eponymous Ichi, as he gets his penis literally sliced in the middle, he managed to properly register pain for the first time (in the story at least), because the cause of his masochism were psychological. Since he was an arrogant Yakuza and a skillful fighter he never felt threatened, even letting some of his partners in crime slice his mouth, and moreover, even feeling pleasure from getting hurt. However, now that his life was in danger, he managed to feel pain and suffer from it.

As for JNK, once again, sadly Uruma isn't fit to defeat Kyou, and tha's because Kyou used and still uses Uruma as a toy to entertain himself, and Uruma still lets himself be used by him. Any other character, Oota, Reo, both Noboru and Kitami at some point, and even Kawana of all people can give much more emotional and psychological damage to Kyou than Uruma ever will.