10 Most Tragic Batman Villains

Batman's mission has cost him a lot of friends. From lovers, to sidekicks, to confidants. But to this day, few of them still sting like the loss of his best friend, Harvey Dent, now known as Two-Face.

When Batman first started out, Harvey Dent was one of the few allies he actually had. Gordon was only vaguely aware of Batman, and what he did know didn't exactly endear him to the caped crusader. But Harvey leapt at every chance to help out his buddy Bruce and this mysterious vigilante who was finally putting down the mob bosses that ran the city like kings.

But then tragedy struck when one of those mob goons threw a cup of acid into Harvey's face, forever scarring the entire right side of his face and his right hand, and breaking his mind in two. Harvey had always been obsessed with duality, and in some interpretations even had a separate personality he kept locked away. But with his face scarred and his hope in humanity gone for good, the other side of him took over and became Two-Face.

Two-Face's tragedy is two-fold. He represents both the tragic fall of a great man who became one of Gotham's most infamous criminals, as well as being a friend that Bruce couldn't save.