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.