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The Riddler is typically portrayed as a smooth-talking yet quirky character, deemed insane by the courts of intense obsessive compulsion and neurosis. This was first introduced in the 1966 issue of Batman (titled, “The Riddle-less Robberies of the Riddler”) in which he tries to refrain from leaving a riddle, but fails. This compulsion has been a recurring theme, as shown in a 1999 issue of Gotham Adventures, in which he tried to commit a crime without leaving a riddle, but fails: “You don’t understand… I really didn’t want to leave you any clues. I really planned never to go back to Arkham Asylum. But I left you a clue anyway. So I… I have to go back there. Because I might need help. I… I might actually be crazy.” It is a theme further explored in the 2003 Batman Adventures story “Free Man,” where Riddler, officially ruled a free man, sells communication technology he developed to an electronics firm only to be pursued by shadow assassins; he turns to Batman for help, only to break down when their trap succeeds and Riddler is seized by an overpowering sense of survivor guilt.
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