Action Comics #51 (DC, 1942)

Armed only with a squirt gun and a "foolproof plot," the Prankster made his leering debut on this smashing cover. While not exactly one of Superman's most powerful foes, he would have enough staying power to be a recurring character through the 1940s-50s. The Prankster was the second major Superman supervillain to grab the limelight on an Action Comics cover. Comics historian Les Daniels wrote about the Mirthful Miscreant's appeal: "A key ingredient in the success of Superman during what is now called the Golden Age of comic books was a sense of humor. 'There was a spirit of fun in the thing' said Jerry Siegel. 'And as a matter of fact, Joe and I, when we first started going into comics, had intended to do a comedy strip. So we were very comedy oriented, and that's why Superman did have this comic flair to it.' Superman couldn't be defeated, but he could be deflated, and many of the most memorable enemies of his early years were clowns. The earliest opponent to really play for laughs was the Prankster. A corny practical joker who considered himself 'the funniest man in the world,' the Prankster had a bulbous body, a scrawny neck, and a goofy gap-toothed grin -- think Mr. Mxyzptlk meets Alfred E. Neuman! Time and again, the Prankster's needling hurt Superman more than a dozen death rays." Fred Ray's portrayal of Superman bursting through a brick wall, drawn using dynamic foreshortening, is magnificent.