Dick Tracy was one of the first superheroes of his kind. That kind being he didn’t use superpowers to thwart his enemies. Yet creator Chester Gould still managed to give Tracy some of the most bizarre, insane, and even loveably interesting adversaries in all of comics.

Take Big Boy Caprice, whom Gould modeled right after legendary gangster, Al Capone. Surprisingly though, Big Boy never interested readers the way many of his minions did. They were the guys doing the “dirty work.” Afterall, Big Boy was just the brains behind the operations. There was no need for him to tarnish his own hands, when he could afford to sully someone else’s. But it was the physically deformed villains that readers really wanted. 

People wanted a henchman who called himself The Blank, a gangster whose face was destroyed by a gunshot; The Claw, an evil character who replaced his hand with that of a cold, metal hook; Flattop, an assassin with a misshapen head; Half-and-Half, much like Batman’s Two-Face, he has one good side and one horribly distorted; Little Face, who had an extremely tiny face on a huge head; Mumbles, a ferocious killer who had untranslatable speech patterns; and perhaps the most memorable – Pruneface, a Nazi agent and spy with a sun-damaged face. When put up against other villains in other comic strips, Tracy’s enemies could certainly hold their own.