In many ways The Dark Knightarticulated and demonstrated the importance of Harvey Dent better than we ever could. Dent is, in so many ways, the biggest failure of Batman's career, and is a constant reminder of the price that can be paid in the battle against evil. Two-Face is a character that has been best served by time, evolving throughout the years from a relatively simple gimmick (similar to many of Batman's foes) to one of the most layered, tragic figures in superhero fiction.

Despite having a dark past, Dent rose through the ranks of Gotham to be a respected District Attorney, working with Jim Gordon and the Caped Crusader to wage a war on crime. Dent falls to a plot organized by the criminals he had been breaking down, and thus was born a new crime figure, one who can't distinguish between right and wrong without the help of his lucky coin.

Like many on this list, Two-Face isn't always a criminal. Several storylines have healed Dent's madness, and scarring, only to have him pulled back into the darkness. These struggles between "Dent" and "Two-Face" only serve to demonstrate the loss Gotham has suffered. The first major victory of organized crime may have been the only one it ever needed. Without Dent consistently on the side of light, Gotham might not stand a chance - Batman or not.