Adventure Comics #180

From the September 1952 issue of Adventure Comics, this cover by Win Mortimer drops Superboy right into the middle of a criminal awards ceremony — a tuxedoed emcee announces the "Blackjack Award" to "Bleak" Mahoney for making a chump out of Superboy, while the Boy of Steel himself stands in the crowd, hands in handcuffs, boldly calling out "I claim the Superboy Award!" The sheer absurdity of a gangland banquet honoring humiliation of a superhero gives this one an irresistible, only-in-the-Silver-Age charm. Interior art by John Sikela brings the story "The Grand Prize of the Underworld!" to life behind that wonderfully offbeat cover.