First Appearance
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Answer
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Detective Comics #36 (Feb 1940)
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Doctor of Psychology
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Dr. Hugo Strange
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Batman #1 (April 1940)
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Expert Burglar and Gymnast
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Catwoman
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Batman #1 (April 1940)
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Certifiably Insane; Prop-Based Weaponry
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The Joker
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Detective Comics #40 (June 1940)
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Malleable Skin; Shapeshifting
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Clayface
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World's Finest Comics #3 (Sept 1941)
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Creates Fear-Induced Hallucinations
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Scarecrow
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Detective Comics #58 (Dec 1941)
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Avian-Inclined Criminal Mastermind
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The Penguin
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Detective Comics #66 (Aug 1942)
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Bipolar Disgraced District Attorney
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Two-Face
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All-American Comics #61 (Oct 1944)
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Unnatural Strength/Stamina; Immortality
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Solomon Grundy
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Batman #49 (Oct 1948)
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Utilizes Mind-Control and Manipulation
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Mad Hatter
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Detective Comics #140 (Oct 1948)
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Genius-Level Intellect; On the Spectrum
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The Riddler
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Batman #59 (June 1950)
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Deadly Assassin; Skilled Marksman
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Deadshot
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Batman #63 (Feb 1951)
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Winged Flight Suit; Web-Like Secretion
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Killer Moth
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Detective Comics #184 (June 1952)
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Jet Pack; Flamethrower
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Firefly
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Detective Comics #259 (Sept 1958)
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Obsessed with Chronology
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Calendar Man
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Batman #121 (Feb 1959)
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Refrigerated Exo-Suit; Cryogenic Gun
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Mr. Freeze
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Batman #181 (June 1966)
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Toxin and Pheromone Secretion
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Poison Ivy
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Detective Comics #400 (June 1970)
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Chipoteran Transformation
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Man-Bat
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Batman #232 (June 1971)
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Immortality; Leader of Ninja Guild
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Ra's al Ghul
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Batman #357 (Mar 1983)
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Reptilian Teeth, Claws, and Skin
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Killer Croc
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Batman #386 (Aug 1985)
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Crime Lord; Hypnotic Suggestion
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Black Mask
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Detective Comics #583 (Feb 1988)
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Crime Lord; Dissociative Identity Disorder
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Ventriloquist
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Batman: Shadow... #1 (June 1992)
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Psychotic Killer; Master Knife-Wielder
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Victor Zsasz
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Batman: Vengeance... #1 (Jan 1993)
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Chemically-Induced Strength and Agility
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Bane
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The Batman Adventures #12 (Sept 1993)
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Skilled Gymnast; Prop-Based Weaponry
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Harley Quinn
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Batman #609 (Jan 2003)
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Master of Disguise; Skilled Marksman
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Hush
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