MTL - Pulling Together a Villain Reformation Strategy - Chapter 1 The beginning of dog blood

When Simon dies, it turns out there's more to combat than lightning reflexes with his controller, and the path to becoming a hero is more brutal than he can imagine as he descends into The Pit. Death after Death is a dark, time loop/Isesaki story with roguelike elements, that explores some of the common tropes in a different light.

He rose from abjection and achieved eternity in glory.
He embraced the prettiest beauties and killed the strongest opponents.
He was able to shift the clouds into rain and cover the sky with one hand.
He could overrun the entire world and go anywhere as he pleased.
He pacified wars and held the world in awe.
He was matchless in the world.
However, his hair turned white overnight for his beloved woman and he was on the verge of death.
He was surrounded by enemies who were trying to take his life.
He struggled his way to become mighty and fought for everything he cherished.
For this age, he was the only king of the Dark World.
His name was a byword for might.
As a man living in the world, his only ideal was to pursue brilliance.

- Description from Novelupdates

Ye Chu is a miserable supporting character from a novel (she transmigrated).

She’s the most famous socialite in Shanghai, but her existence was to emphasize the magnificence of the white lotus female lead.

In the previous life, Ye Chu died in an accident. After rebirth (still in the novel), she didn’t only want to get revenge, but also change her fate, allowing every side character to have the opportunity to shine. Ye Chu and Lu Huai are a fake couple in their previous lives but reunited in this life.

They probed each other at every turn and slowly got closer to each other. They two fell for each other and confronted their enemies together.

- Description from Novelupdates