Hugh Hefner was famously supportive of cartooning in the pages of Playbpy for decades, in part because he was a frustrated artist himself. Samples of his own attempts at single panel humor surface from time to time in biographies of the legendary publisher and the history of his landmark magazine. Less well-known is that in 1951 and prior to his meteoric Playboy fame he published a collection of his own comic work focused on the theme of his beloved Chicago., That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals. This was very much an insiders’ cartoon revue, as Hef broke the volume into Chi-town’s famous districts and infamous institutions like The Loop. Michigan Avenue, Bug House Square, North Clark Street, The El, and the activities for which they were famous: strip bars, b-girls, the city’s multiple newspapers, soapbox orators.

Clearly Hef was not half bad as a cartoonist. His overall blocky style feels a bit amateurish, but he had a knack for etching in small facial expressions that added to the comedy. His humor clearly previewed Playboy’s. Like Hef himself, the sexual jokes were at once bawdy but still a bit repressed in his signature mid-western style of a buttoned-down satyr. Hef was famous for his heavy editing of cartoonists, and you can see here how his tone timid licentiousness would in form the more talented cartoonists he would employ for Playboy.

Comic strip lovers will especially appreciate the panel below where he references the legendary conservatism of The chicago Tribune’s owner/publisher Colonel Robert McCormick.

A full copy of That Toddlin’ Town can be found at the Internet Archive. A print reprint was published a decade ago as well.