Mad #59

Mad's Special Halloween Issue from December 1960 leans into spooky-season fun with a cover by Kelly Freas that reimagines the Headless Horseman with a delightful twist: Alfred E. Neuman's gap-toothed face glows like a jack-o'-lantern where the rider's head should be, while a menacing pumpkin-headed figure looms behind him atop a ghoulish green phantom horse thundering across a midnight landscape beneath a blazing orange moon. The atmospheric painting — all swirling roots, wild mane, and wild-eyed steed — captures genuine Halloween dread before the joke fully lands. Al Feldstein helms the interior as writer, artist, inker, and letterer, making this a remarkably hands-on issue from one of comics' most versatile talents.