Pruneface
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Pruneface was a villainous character in the long-running comic strip Dick Tracy, drawn by cartoonist Chester Gould.
Pruneface, whose real name was apparently "Boche" (French for "German," so it might have been a code name), was a brilliant industrial engineer who had a horribly deformed face, which had led to social rejection which apparently so poisoned his mind that he sold out to the Nazis and was involved in espionage against the US, as well as the development of nerve gas. Although Pruneface apparently died at the end of his original storyline, freezing to death in a blizzard, he was revived in the 1980s by Gould's successor, Max Allan Collins. By the time he came back, his wife Mrs. Pruneface had already died trying to avenge him.
The character was also a featured villain in the animated version which aired intermittently in the U.S. as a children's program, primarily in the 1960s. In that version, the character (voiced by Mel Blanc)'s voice was modeled after Boris Karloff.
He also made a brief appearance in the Dick Tracy movie starring Warren Beatty. Though he was a Nazi spy in the strip, in the movie he was an American mobster, operating in Tracy's city, who accepted Big Boy as his superior. He was eventually gunned down by the mysterious villain, The Blank.