For Laughing Out Loud #32

Dell's long-running humor digest serves up a perfectly absurd gag on this 1964 cover, where a cheerful blonde in a bikini floats on a raft clutching her "First Prize – Fancy Hat Competition" ribbon — her towering, wildly colorful bird-topped headpiece explaining exactly how she earned it, while a swamped boat and bewildered onlookers bob in the background. Richter's loose, expressive linework sells every bit of the joke with a cartoonist's confident timing. Self-proclaimed "Number One with the Jest Set," For Laughing Out Loud was clearly earning that title one groan-worthy punchline at a time.