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Dana Dodrill
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"Dana was a hill-billy crooner... and rather good, too" says the intro to "The Singing Slayer" story of comic book Crime Does Not Pay #37 (January 1945). He's from Webster County, West Virginia and the year is 1943. He's down on his luck and outta money when he overhears a local has a lot of cash on hand. He offers the guy a ride, drives him out to the country, strangles him for the money, and sings afterwards.
Emboldened, he robs a couple and decks the wife as he sings. He's caught, sings in jail, declared sane by the doctors, sentenced to death, and then has his sentence commuted to life by the governor, who thinks he's not "of normal intelligence."
