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Golden Age
Two-Face's debut and Golden Age origin story, 1942's "The Crimes of Two-Face" (Detective Comics #66), introduced him as Harvey Kent, a handsome law-abiding Gotham City district attorney prosecuting mob boss Sal Maroni. During the trial, after Kent presents Maroni's lucky two-headed coin as evidence, Maroni throws acid at Kent's face and disfigures it in half. Kent, driven insane by society's repulsion and his wife's nonacceptance of his new appearance, scars one side of Maroni's two-headed coin to symbolize his duality, then flips the coin to decide whether to become a criminal or wait for the only plastic surgeon able to fix Kent's face, who was caught in a concentration camp in Germany, to arrive. With the scarred side of the coin being the result of Kent's coin flip, Kent decides to become a criminal with the alias Two-Face who depends on flipping his coin to determine whether to be evil or good; afterwards, with the coin landing on the scarred side, Two-Face robs a bank, then, with the coin landing on the unscarred side, gives his loot to charity, causing confusion between the police and populace, whose opinions are divided about Two-Face's morality. The rest of the issue features Two-Face committing a series of crimes centered on the number 2, one of which is stopped by Batman, who pursues and corners Two-Face after he escapes. Batman makes Two-Face a proposition to give himself up and start over, by which Two-Face replies that the coin makes all his decisions for him, then flips the coin. The issue ends with the coin landing on its edge, making Two-Face leave his life to fate, with the story being resolved in "The Man Who Led a Double Life!" (Detective Comics #68). Harvey Kent is cured through plastic surgery in 1943's "The End of Two-Face" (Detective Comics #80), and is shown reformed in 1952's "The Double Crimes of Two-Face!" (Detective Comics #187). The last appearance of the Golden Age version of Harvey Dent was in Superman Family #211 (October 1981), depicting him as a guest at the marriage of Bruce Wayne and Selina Kyle.

Bronze Age
In Two-Face's Bronze Age reintroduction, "Half a Life" (Batman #234), Two-Face concocts an elaborate scheme to steal doubloons from a historical schooner, which Batman realizes and attempts to stop. As Batman approaches the ship, Two-Face finds and incapacitates him, then ties him up, eventually leaving the ship after he lets it sink. Before Two-Face leaves, Batman tries to convince Two-Face to flip his coin to save an old man unwittingly caught in the trap by reminding him that he is both good and evil; Two-Face first disagrees until after his departure from the ship in which he is unable to resist flipping his coin. With the coin landing on the unscarred side, Two-Face returns to the ship to rescue the old man, then sees Batman had escaped his restraints. Batman offers Two-Face to surrender, to which Two-Face disagrees and attempts to attack Batman, with Two-Face being knocked out unconscious by Batman afterwards. "Half a Life" also includes a recap of his Golden Age stories as his origin: from his transformation to Two-Face and his subsequent reformation to his criminal relapse, as depicted in the 1954 story "Two-Face Strikes Again!" (Batman #81), in which Dent's plastic surgery is disfigured after he attempts to chase down robbers, causing his return as Two-Face.

In "Threat of the Two-Headed Coin!" (Batman #258), Two-Face is broken out of Arkham Hospital by a retired United States Army general who hires Two-Face to blackmail the United States government with an atomic bomb. After Two-Face betrays the general and takes over his plan, the general reveals the scheme to Batman, then dies by suicide out of remorse. Later, in the United States Capitol, Two-Face interrupts a Congress meeting to carry out the extortion scheme: in exchange for not exploding the Capitol with an atomic bomb, Two-Face demands the United States government to give him two billion dollars and gemstones, with Two-Face intending to use the money to bribe people to ignore his hideous appearance and end his misery; Batman eventually foils Two-Face's plan.

Two-Face then appears in a number of non-Batman comics, such as The Joker, Justice League of America, and Teen Titans. The Joker's first issue, "The Joker's Double Jeopardy", features Two-Face and fellow Batman adversary Joker battling each other to prove who is the superior criminal, while in Justice League of America's 125-26th issues, Two-Face assists the Justice League. In Teen Titans, Two-Face meets Teen Titans member Duela Dent who claims to be his daughter.

In the 313-314th issues of Batman, Two-Face steals a top secret missile activation binary code owned by the United States government and goes to New Orleans, with Batman and a United States federal agent reluctantly working together to trail him and obtain the code. At a float in New Orleans' Mardi Gras parade, Two-Face tricks and steals $44,000,000 from an American and a Russian representative who each negotiated earlier for the code for $22,000,000; Two-Face then escapes from the float to a blimp, with Batman and the agent in pursuit. Afterwards, while Batman hangs from the blimp's hatch, Two-Face flips the coin to decide whether to kill him, with the agent eventually shooting the coin outwards the hatch. Two-Face, declaring that his life is meaningless without the coin, leaps for it and falls out of the blimp.

Two-Face changes his face and identity in Batman's 328-329th issues to Carl Ternion, and reunites with his wife to make her happy after her former husband, Dave Stevens, died. Two-Face then avenges Stevens' death by killing Sal Maroni, who had also changed his face and identity to Anton Karoselle and killed Gilda Dent's former husband; Karoselle's death and Two-Face and Maroni's changed identities are significant aspects of the mystery Batman solves in the story: a video tape sent to him by Two-Face as Carl Ternion, in which Ternion admits he had murdered Karoselle and had been acquitted for it. Later, Two-Face runs away from Gilda Dent after his plastic surgery becomes undone, then afterwards, Batman tells Gilda Dent the truth about Ternion's actual identity and convinces her of a plan to lure and take down Two-Face: Batman disguises himself as Maroni attacking Gilda Dent as bait, and, with Two-Face chasing him, leads Two-Face to the Gotham City courthouse. Batman and Gilda Dent eventually convince Two-Face to rehabilitate himself in Arkham.

In the two-issue arc "Half a Hero... Is Better Than None!" from Batman #346 to Detective Comics #513, Two-Face escapes Arkham Asylum and puts Batman in an elaborate deathtrap set in a converted halfway house, eventually capturing Batman and imprisoning him for a week. Batman then escapes by creating and putting on a Two-Face mask, causing Two-Face to release him.