6. Finally Killing Uncle Paulie - The Darkness
Woof. This one hit hard.
Now let's make no bones about it: Jackie Estacado is not a man who wears a white hat. He's in the mob after all so it's clear his conscience isn't entirely clean. However, thanks to Uncle Paulie being the embodiment of a dirty scrotum, Jackie looks like an angel by comparison.
Uncle Paulie, in a bid for control of the district, attempts to murder Jackie, then goes on to use his corrupt cop pal Eddie to kidnap his girlfriend Jenny and proceeds to execute her right in front of him.
From here, using his demonic powers and an arsenal that seems never-ending, Jackie tears up the city leading to you finally plugging that fat lump Paulie at the top of a lighthouse. Even with The Darkness telling you that it will own your soul by killing him, Jackie still chooses to pull the trigger. It's a depressing end, but one that metes out vengeance in brutal form.