SO! In the book, Supervillains and Philosophy (2009), legendary Batman author Denny O'Neil wrote an essay/fic about Harvey Dent! Neato keen!

Wow, O'Neil, a philosophically-driven writer with tons of Batman experience, writing about Two-Face? Oh, oh, do tell, what's it about?! WELL, apparently, Harvey Dent was a... um... fervent Christian and Calvinist, huh, okay, who got into law for the sole purpose of punishing criminals as a... er... holy crusade against sinners... wait... and he also rejected the philosophies of existentialists and Nietzsche as "blasphemy," no, that's not... that is, until he got hit by acid, at which point he... he...
... Okay, y'know what? Let... let's just stop right there.
*presses temples, takes a deep breath*
Look. Here's the thing. I've gotten really frustrated trying to find ANYTHING related to Harvey (or, for that matter, any of the other Batman villains other than the Joker) in essay collections such as Batman and Philosophy: Dark Knight of the Soul, Batman Unmasked: Analyzing a Cultural Icon, or the O'Neil-edited Batman Unauthorized: Vigilantes, Jokers, and Heroes in Gotham City. The closest anyone's come to anything is an essay about Batman and "The Elusiveness of a Complete Friendship" in Superheroes and Philosophy: Truth, Justice, and the Socratic Way where Harvey was briefly examined in terms of his friendship with Batman. Even then, he's discussed only as an adjunct to Batman's own issues, not for his own philosophical value.
I just don't get it. I know I'm biased and all, but seriously, if you're going to talk about comics characters and philosophy, isn't Two-Face one of the most obviously rich sources of discussion material? He hits so many classic themes, from good and evil, the duality of man, fate versus chance, punishment versus rehabilitation, the responsibility (or lack thereof) of one's own actions, justice and balance... and those are just the ones that come to mind! Why is the Joker considered such a fount of philosophical debate, when Two-Face lends himself so perfectly as a humanized symbol of age-old questions?

Hmmm... good and evil in one character, you say? Nope, I just don't see it.
So finally, when someone actually DOES tackle Harvey head-on, they do it by using the character as a strawman for a look at "religious fanaticism versus existentialism." These are themes which don't fit Harvey Dent. Like, at all. So to accomplish this, O'Neil crafts a whole new backstory and origin for the character, to the point that he barely resembles Harvey Dent at all. I'd expect this from a pompous philosopher who only has a passing knowledge of the characters from the films and a couple big-name comics, but this is Denny O'-fucking-Neil, a guy with over thirty years' experience as both writer and group editor of Batman comics! This is a guy who KNOWS the stories, who could have easily had something to say about them and the character as he's been presented, but instead chose to bend the character over backwards for his own ends.
I'd love to post the whole thing, just so those better versed in theology and/or philosophy could tear this apart more thoughtfully than I'm able, but the best I can do is post available snippets from the pages of Supervillains and Philosophy up at Google Books and do my best to describe the rest.
( Two Fates for Two-Face behind the cut! )
Thing is, O'Neil has repeatedly displayed a fascination for Eastern philosophy in comics like The Question, and considering how many times creators have tried slapping a yin-yang symbol on Two-Face, it makes me wonder why he hell O'Neil didn't try being the first to tackle Taoist themes in the character. It just seems like such an obvious fit in retrospect. Man, now I'm imagining a whole story with the Question (Charlie/Vic) raising all manner of philosophical themes to Harvey, as well as challenge the preconceived notions of Two-Face to other characters such as Batman, Gordon, Dick, and Renee. The Faceless Man exploring the philosophies surrounding the man with Two Faces: why the hell hasn't O'Neil written this, like, yesterday?
A good question, I suppose. And one of many that will go unasked until somebody finally explores the vast thematic, literary, and philosophical potential that Harvey Dent potentially represents. Well... somebody other than me, at any rate.
*ETA: Regardless of what some fans or Batman: Face the Face would have you believe, it's never been canon that Harvey Dent was in any way a vain person before or after the acid attack. That's a whole other rant I need to explore in the near future.

Wow, O'Neil, a philosophically-driven writer with tons of Batman experience, writing about Two-Face? Oh, oh, do tell, what's it about?! WELL, apparently, Harvey Dent was a... um... fervent Christian and Calvinist, huh, okay, who got into law for the sole purpose of punishing criminals as a... er... holy crusade against sinners... wait... and he also rejected the philosophies of existentialists and Nietzsche as "blasphemy," no, that's not... that is, until he got hit by acid, at which point he... he...
... Okay, y'know what? Let... let's just stop right there.
*presses temples, takes a deep breath*
Look. Here's the thing. I've gotten really frustrated trying to find ANYTHING related to Harvey (or, for that matter, any of the other Batman villains other than the Joker) in essay collections such as Batman and Philosophy: Dark Knight of the Soul, Batman Unmasked: Analyzing a Cultural Icon, or the O'Neil-edited Batman Unauthorized: Vigilantes, Jokers, and Heroes in Gotham City. The closest anyone's come to anything is an essay about Batman and "The Elusiveness of a Complete Friendship" in Superheroes and Philosophy: Truth, Justice, and the Socratic Way where Harvey was briefly examined in terms of his friendship with Batman. Even then, he's discussed only as an adjunct to Batman's own issues, not for his own philosophical value.
I just don't get it. I know I'm biased and all, but seriously, if you're going to talk about comics characters and philosophy, isn't Two-Face one of the most obviously rich sources of discussion material? He hits so many classic themes, from good and evil, the duality of man, fate versus chance, punishment versus rehabilitation, the responsibility (or lack thereof) of one's own actions, justice and balance... and those are just the ones that come to mind! Why is the Joker considered such a fount of philosophical debate, when Two-Face lends himself so perfectly as a humanized symbol of age-old questions?

Hmmm... good and evil in one character, you say? Nope, I just don't see it.
So finally, when someone actually DOES tackle Harvey head-on, they do it by using the character as a strawman for a look at "religious fanaticism versus existentialism." These are themes which don't fit Harvey Dent. Like, at all. So to accomplish this, O'Neil crafts a whole new backstory and origin for the character, to the point that he barely resembles Harvey Dent at all. I'd expect this from a pompous philosopher who only has a passing knowledge of the characters from the films and a couple big-name comics, but this is Denny O'-fucking-Neil, a guy with over thirty years' experience as both writer and group editor of Batman comics! This is a guy who KNOWS the stories, who could have easily had something to say about them and the character as he's been presented, but instead chose to bend the character over backwards for his own ends.
I'd love to post the whole thing, just so those better versed in theology and/or philosophy could tear this apart more thoughtfully than I'm able, but the best I can do is post available snippets from the pages of Supervillains and Philosophy up at Google Books and do my best to describe the rest.
( Two Fates for Two-Face behind the cut! )
Thing is, O'Neil has repeatedly displayed a fascination for Eastern philosophy in comics like The Question, and considering how many times creators have tried slapping a yin-yang symbol on Two-Face, it makes me wonder why he hell O'Neil didn't try being the first to tackle Taoist themes in the character. It just seems like such an obvious fit in retrospect. Man, now I'm imagining a whole story with the Question (Charlie/Vic) raising all manner of philosophical themes to Harvey, as well as challenge the preconceived notions of Two-Face to other characters such as Batman, Gordon, Dick, and Renee. The Faceless Man exploring the philosophies surrounding the man with Two Faces: why the hell hasn't O'Neil written this, like, yesterday?
A good question, I suppose. And one of many that will go unasked until somebody finally explores the vast thematic, literary, and philosophical potential that Harvey Dent potentially represents. Well... somebody other than me, at any rate.
*ETA: Regardless of what some fans or Batman: Face the Face would have you believe, it's never been canon that Harvey Dent was in any way a vain person before or after the acid attack. That's a whole other rant I need to explore in the near future.