DEATH BATTLE: DIO VS Esdeath

JoJo's Bizarre Adventure vs Akame ga Kill!

Connections:

Both of them begin as powerless humans, getting by using their wit and their cunning on the outskirts of society (Dio living in backwater the slums of London, using his intelligence to hustle people in chess and make something of a living while poisoning his father, whereas Esdeath living in a cunning hunter tribe in the northern lands beyond the imperial capital hunting Danger Beasts) After their parents died though, a death they did not mourn although for different reasons (Dio being his father's killer, and Esdeath believing due to her ideology that her father was weak and didn't deserve pity) they left the outskirts and went to the "big city," rising to a new and important position (Dio becoming a member of the Joestar Family Esdeath becoming a general in the Imperial Capital)

During their time in these positions, they gained a new power related to the consumption of blood based on a powerful artifact which empowered their bodies and gave it new abilities, including ice manipulation (Stone Mask and Demon's Extract respectively) leading to them becoming somehow even more diabolical and evil than they already where, or at least allowing them to exercise their cruelty to a greater extent

Both of them in these positions also meet a kind-hearted, sword wielding boy (Jonathan Joestarand Tatsumi respectively) who have the powers and abilities of a dead person (Will A. Zeppeli and Bulat respectively) although their views on them are different (Dio despising Jonathan for merely existing whereas Esdeath loved Tatsumi for meeting all of her requirements for a mate)

Both also assemble an army or group to conquer them, their allies/descendants and what they stand for (the Agents of Dio and Jaegers respectively)

Both of them create a new move with their powers which is the ability to stop time (The World and Mahapadma respectively)

Both of them are eventually killed by the protagonists of their series (Jotaro Kujo and Akame respectively) who wields similar abilities to them (Jotaro's Stand Star Platinum and Akame's Teigu Muramase), who in many ways was similar to them (Jotaro is similar to Dio in the fact that Dio now has the body of a Joestar, and since Star Platinum is technically a descendant of The World kinda, they are the same stand and therefore Jotaro also has Dio's Time Stop. Akame being similar to Esdeath in the sense that they're both, or Akame used to be, killing machines created to serve the interests of the Imperial Capital, although Akame was able to break free of that)

Both have a god complex of some kind (Dio believing he can reach a place "Over Heaven," being worshipped as a god by Pucci, given "Dio" is Italian for god. Esdeath she believes that might-makes-right within the world, something of an animalistic hierarchy where the strong get to rule and dominate over the weak, and she believes herself to be the strongest)

Both also use bladed weapons (knives and a rapier respectively)