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Gotham District Attorney Harvey Dent was a true guardian of law and order. Well-regarded as a fearless law enforcer, he had a reputation for producing results. However, the man had a hidden dark side. Dent suffered from a severe mental illness, multiple personality disorder, that developed since childhood when he mistakenly believed he seriously wounded a bully in fit of anger, when in fact he was hospitalized for an unrelated case of appendicitis. As a result, a guilty Dent repressed his violent emotions. His rage, however, never truly subsided, and the pent up anger formed an opposing personality to that of the mild-mannered Dent. The malevolent alternative personality, named "Big Bad Harv", often seized control in stressful situations. Dent had no recollection of any occurrences while Big Bad Harv was in present; the dark side dominated completely.
At some point in his life, he met and dated Pamela Isley, alias Poison Ivy, who tried to kill him by poisoning in revenge for the near-extinction of the Wild Thorny Rose for the construction of Stonegate Penitentiary but was saved by Batman, who got the antidote to him in time.
Though Dent controlled himself for many years, the re-election campaign proved so stressful that the violent episodes became frequent, to the point where his psychiatrist recommended committal to a psychiatric ward in order to prevent a traumatic psychotic break. However, such an action would have been political suicide and Dent instead compromised, agreeing to a reduced campaign effort and increased medical treatments.
Mob boss Rupert Thorne learned of this situation, and acquired Dent's medical files. As Thorne was the target of Dent's current campaign, he used the files to blackmail the District Attorney into backing off. The high stress situation caused Dent to surrender his mind to Big Bad Harv, and he attacked Thorne. During the fight, a freak explosion deformed the left side of Dent's body. The trauma was powerful enough to force his alternate personality to dominate, and left Dent in a state where right and wrong no longer held any meaning. Instead, random chance reigned supreme.
Dent became "Two-Face" and turned to a life of crime. Using the element of chance, Two-Face attacked various Thorne operations, including night clubs and gambling rings. However, the victims were always left to a coin flip from Two-Face's dreaded double-headed coin. Over the course of six months Thorne lost substantial amounts of money and the mobster put a two million dollar bounty on the former attorney's head, one million for each face.
Two-Face, done with humiliating Thorne, decided to return the favor the mobster gave him, and stole Thorne's criminal files. With that information in hand, he planned to blackmail Thorne into leaving Gotham altogether. However, Thorne's accomplice Candace acted as a detective of the Gotham Police Department and contacted Dent's ex-fiancé Grace Lamont, tricking her into contacting Thorne if she heard from Two-Face. As predicted, Two-Face arranged a meeting with her, and Grace contacted Thorne. Thorne attempted to end Two-Face altogether, but Batman intervened, and in the end, Thorne was left at Two-Face's mercy. When Two-Face made his coin flip to decide Thorne's fate, Batman tossed a box of coins into the air, preventing Two-Face from finding his coin. He went mad, unable to make a decision without testing chance. He was arrested, and sent to Arkham Asylum.
Two-Face remained quiet on the crime scene for some time. Though he made a few attempts to kill Batman (one of which he described at a poker game), he never succeeded and either escaped or returned to Arkham. However, he began a new gang, and had his man Gil Mason infiltrate the Gotham justice system. Mason became the new Deputy Police Commissioner, and provided quick results courtesy of Two-Face's information. Rupert Thorne was arrested, and with Thorne out of the way, Two-Face had control of Gotham's seedy underbelly. However, underworld control does little good if there is still a law presence existing to bring one down, and the ever calculative Two-Face knew this. Planting evidence and staging assassination attempts, Two-Face brought Commissioner Gordon down by linking him to Rupert Thorne, and used Mason to arrest him.
However, Batgirl knew the allegations were untrue and began her own investigation, soon discovering Gil Mason was a corrupt official. His trail lead her to Two-Face, as well as Batman and Robin. Two-Face and Mason planned to kill Gordon at Bayshore Wharf. However, Batman, Robin, and Batgirl prevented the attempt, and Two-Face and Mason were arrested.
When the Arkham inmates banded together to devise a plan to eliminate Batman, Two-Face simply wanted to kill him and end the ordeal. However, he lost the coin flip and instead served as the prosecution for the Trial of Batman.
Bruce Wayne never gave up hope that Two-Face could once again return to normal society as his friend Harvey Dent. He continuously paid for counseling to subdue the Two-Face persona. After some time, doctors agreed his therapy had been effective enough to stabilize Two-Face's mind, which then allowed the opportunity for surgery upon Harvey's damaged side. Just when the surgery was about to begin, masked mobsters broke into the operating room. Stating only that their "boss" wanted to handle Dent personally, two cars split from the scene. One took Two-Face to Stonegate, the current whereabouts of the Penguin, while the other vehicle was registered to Rupert Thorne. Both criminals had had histories of conflict with both Two-Face and Dent, but neither claimed involvement to Batman and Robin.
In truth, Two-Face kidnapped himself to prevent Harvey from eliminating his other persona completely. Staging the break in, he arranged for his thugs to break him out of the operation and staged a two-pronged getaway, both to allude suspicion and to leave a trademark hint. Though Batman discovered the true kidnapper, he was unprepared for the ambush Two-Face had devised. Capturing Batman, Two-Face placed his life in the flip of the coin. During their earlier struggle, Batman switched the real coin with a trick one, designed to always land on its side. Two-Face, however, couldn't handle the indecision, and chased his coin on to a support beam overhanging Gotham. The coin fell off and in a desperate gamble, he managed to grab it but fell off in the process and was unable to pull himself back up. Batman caught hold of Two-Face at the last second, but needed Two-Face to pull himself up. The coin, however, couldn't decide for him; the choice was up to Two-Face alone. The Harvey Dent persona resurged for a moment, and he dropped the coin, but Two-Face took control once more and sabotaged the effort. He plummeted, but Batman and Robin managed to save him and themselves in time. Two-Face was once again sent to Arkham for more psychiatric treatment. Still, Harvey Dent emerged once more to thank his friend Bruce Wayne for not giving up on him.
After Two-Face escaped, small time crook "Shifty" Drake stole chemicals from him. Drake skipped town, but left his son Tim Drake behind with a key to a locker at Gotham Airport. Two-Face took the key and planned to kill Tim, but Batman intervened. Meanwhile, Two-Face reacquired the chemicals, and held the entire city hostage, threatening to create a toxic gas unless he received twenty-two million dollars. However, the city refused to pay and after a two-minute warning, Two-Face activated the chemicals. Batman and Batgirl arrived to stop them, and shortly thereafter Robin. The trio stopped the machine and apprehended Two-Face once more.
Eventually, Harvey Dent developed a third superego personality known as The Judge, a ruthless vigilante. The Judge brutally attacked Gotham's criminals, including Two-Face himself, placing their lives at risk. Batman eventually deduced the Judge's true identity and captured him. Two-Face was last seen in Arkham, hearing the Judge's voice condemning him, bowing his head and repeating, "Guilty... guilty... guilty...".
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