Caliborn - tries to kill his own sister, destroys entire universes, attempts to kill protagonists, makes some horrible objectifying remarks about women, brainwashes and enslaves people to do his dirty work.
Dirk - oh boy, where do I even START. He was originally a protagonist in the first Homestuck comics, but then it turned out that he went ... omniscience-mad? It's kind of difficult to explain but basically, he was aware of everything his alternate universe selves were aware of and that is TOO MUCH POWER FOR ANY ONE MAN, EVEN ONE AS SMART AS HIM, so he started pulling the strings of all his friends, set off a racist dictatorship, made another friend poop his pants on stage, convinced a third friend to semi-kill-herself to become a robot and is now apparently trying for grand ruler of the multiverse? Unless that's also part of his terrible scheme-within-a-scheme, I honestly don't know, I have given up on trying to make sense of all of this, but Dirk is DEFINITELY into villainous territory now and it's kind of sad BUT it gives me a reason to nom him for this, so yeah.
Homestuck villains
Dirk - oh boy, where do I even START. He was originally a protagonist in the first Homestuck comics, but then it turned out that he went ... omniscience-mad? It's kind of difficult to explain but basically, he was aware of everything his alternate universe selves were aware of and that is TOO MUCH POWER FOR ANY ONE MAN, EVEN ONE AS SMART AS HIM, so he started pulling the strings of all his friends, set off a racist dictatorship, made another friend poop his pants on stage, convinced a third friend to semi-kill-herself to become a robot and is now apparently trying for grand ruler of the multiverse? Unless that's also part of his terrible scheme-within-a-scheme, I honestly don't know, I have given up on trying to make sense of all of this, but Dirk is DEFINITELY into villainous territory now and it's kind of sad BUT it gives me a reason to nom him for this, so yeah.