We recently did a piece on the most heartbreaking video game deaths, and looking back over that list we noticed something odd. Of the five deaths featured, two were out and out villains, one was at best neutral in a global good-vs.-evil struggle, one was a hero but part of the heartbreak was that she managed to use a villain's love for her to kill them both, and the last was more of an antihero whose actions included fratricide.
What the point? It's basically that the modern world of fiction demands more of its antagonists than one-dimensional malice. We demand a human face to identify with, even as we're rooting for that face to get punched. Mulling this over, we began to explore the world of Batman and his incredible rogue's gallery. Despite his having arguably the most psychotic group of adversaries in history, even that group of wackaloons managed to pull through and do the occasional good deed.
Deadshot isn't one of Batman's bigger threats, and in a world with assassins like Deathstroke he is often outclassed. However, he's managed to hold his own over the years due to his incredible disregard for human life, including his own. When your stated goal is to die in a grand firefight, but you're such an expert killer that no one has managed to do it yet, then that is indicative of a rare genetic condition in which a man is born entirely without fucks to give. Apparently Deadshot never bothered to sign up for the transplant list.
Example: Instructions to Deadshot are, quote, stop this guy from killing a senator. Deadshot's response? Kill the senator himself. He's like an evil genie that answers all your wishes with bullets. Including the wishes of his daughter.
Deadshot finds out that not only does he have a child, but she lives in a horribly crime-ridden part of Star City, which is Green Arrow's turf. Feeling that he should do some good for the girl, but being well aware that all his contributions to society involve exit wounds, he proceeds to start massacring criminals where she lives. With the streets safer, he fakes his own death, knowing that shooting people in the head may not be the best qualification for being a good father, and then asks Green Arrow to get off his ass and patrol the area she lives more.
It's hard to really get behind Jervis Tetch's Mad Hatter as a threat, though without a doubt his mind-control technology, pedophilic overtones and just in general creepiness keep him in regular rotation as a good villain in various comic series.
In the animated series, where he is played by honest to God Roddy McDowell, Tetch is a somewhat sadder figure obsessed with Lewis Carroll and his pretty secretary, who he is too shy to approach. Batman thwarts his plan, and the Hatter plots his revenge. His revenge is a plan of diabolic genius and morbid evil in which he...gives Batman the perfect life.
He manages to slip one of his mind-control discs onto Bats, and instead of using it to make him shoot himself in the head, or reveal himself to the public, or even something grandiose like making him commit crimes, he traps him in a dreamworld where his parents are alive, Gotham is free of criminals and he is dating Selena Kyle. For some reason, Batman fights out of this world and back to the real world, where he manages to confront Tetch. Breaking down completely, the Hatter simply says, "You ruined my life. I was willing to give you any life you wanted to stay out of mine." Honestly, it's probably the nicest thing anyone's done for Batman in years.
Harvey Dent has it rough. His superpower is being both hideous and crazy, but he's not as good at those things as, say, Joker. Nevertheless, he remains one of Batman's worst foes, sadly because he does try so often to reclaim his life as a crusader of good but fails to the power of his own madness.
By way of a for instance, one person does manage to get through to the Dent side of Two-Face, lesbian officer Renee Montoya (also the second Question). Dent responds to her kindness by falling in love with her, and knowing that not being female will probably nix any chance of his love being reciprocated, he frames her for murder, hoping that when she hits rock bottom she'll have no other option but to turn to him. That kind of logic is what keeps him a villain.
A lot of Two-Face's psychological problems stem from his father, who would use the two-headed coin that eventually became his son's trademark in a hellish nightly guessing game that always resulted in a beating. Despite this, it is revealed that through both his life as district attorney and as gang leader, Dent spent considerable money making sure that his father spent his twilight years in an expensive nursing home rather than on the street.
For our money, Joker is one of the best -- if not the best -- comic book characters ever created. The Clown Prince of Crime remains beyond all definition and dissection because he is insane the way Superman is strong. To quote Trickster, "When super-villains want to scare each other, they tell Joker stories."
And yet, back before Alan Moore pretty much solidified Joker's origin in the Killing Joke, it was tackled in Batman Confidential. In that book, Joker is Jack, a gangster who has grown bored with life and is feeling a lack of challenges. Luckily, he has a conversation with a waitress and medical student named Harleen Quinzel, who reassures him that Jack is good at his job and encourages him to set a goal in order to help him find something to live for.
Unfortunately, Jack makes his goal beating Batman, and that ends with disfigurement and feeling Jokerized. Still, even after falling out of the crazy tree and hitting every branch and squirrel nest on the way down, Joker never forgets the woman who helped him turn around his life. Anonymously, he pays off Quinzel's entire medical school tuition. This ends up badly in the long run, but give the clown some credit for trying.
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Croc is one of our favorite Batman villains, though his depiction varies widely depending on who's doing the book. He's run the gamut from thug with roid rage and bad skin to bestial, cannibalistic throwback more dinosaur than man. In all incarnations, he's a powerful, primal force that is more than a match for Batman.
In the rebooted universe, he's made just one appearance, but that appearance is amazingly new and different. In the third issue of Red Hood and the Outlaws, a guardian takes Roy Harper's most precious memory as collateral. When the guardian looks at that memory, he sees Harper attempting to kill himself by fighting Croc.
At this point, Harper is an alcoholic, has lost everything when his mentor Green Arrow kicked him out of the sidekick gig as well as taking away his place to live and all his money. Now, he just wants out, and figures that dying in battle with Croc will qualify him for a hero.
Croc picks up on this, having read about Harper losing his shares in Green Arrow's company in the newspaper, and proceeds to talk him down. He encourages Harper to pull his head out of his ass and learn to actually live. In later issues, it's revealed that Croc is actually Harper's AA sponsor, a role that we imagine is slightly easier when you're 8 feet tall and have the reputation of eating people who fuck with you.