Esquire Magazine published their legendary first issue in October 1933 featuring the likes of Ernest Hemingway, John Dos Passos, Ring Lardner Jr., Joseph Auslander and Douglas Fairbanks Jr. Despite it’s lofty list of famous contributors, Esquire’s introductory edition was still quite lacking in comparison to it’s subsequent issues, because it was missing one crucial component: Esky. You could say that it wasn’t until Esquire’s second publication in January of 1934 that they found their spirit, or at least their spirit animal for that matter. Right there on the second cover, was Esky, a bug eyed figure, with an up-turned mustache, and slicked back hair, climbing into a martini glass wearing a full tux and tails. From that issue onward, Esky was embodiment of the Esquire attitude, he was well-dressed, jocular, and just sophisticated enough to forgive his indiscretions.
Created by long-time Esquire cartoonist E. Simms Campbell (who was a legend in his own right as the first African-American cartoonist to have his work published in a national magazine) Esky has appeared on more than five-hundred copies of Esquire over the year, popping up in just about every scenario imaginable. Back when men still got dressed up for daily life, Esky turned mundane scenes of work and life into a stage, and for the early readers of Esquire this became a mantra to live by. He might’ve been a mere cartoon character, but Esky was as well dressed as anyone that’s graced the pages of Esquire, donning everything from herringbone overcoats, to double breasted suits, to gingham check jackets, to spread collar shirts, to military garb, and everything in between. He unfortunately doesn’t get the honor of appearing on their covers anymore, but from his debut to August 1945, Esky enjoyed an unbroken streak where he was the focal point of every single cover. At the time, Esquire’s slogan was, “The Magazine for Men,” and Esky was certainly that man.