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Long before he started Playboy—going well back into his childhood at Sayre Elementary, through high school, anatomy classes at the Art Institute, newspapers in the Army and at the University of Illinois—Hugh Hefner wanted to be a cartoonist. And, perhaps, if he’d been good at it, Playboy never would have existed.

But… he wasn’t. And a little book of his work survives as testimony. At the age of 25, two years before Playboy hit the stands, Hef published That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals. You can see the roots of Hefner’s magazine empire in his sketches—a self-aware sense of humor about the young men of means on North Clark Street and their adventures in the city’s nightlife, casual toplessness drawn in the urbane style of the New Yorker and mixed with hokey, middlebrow take-my-wife-please punchlines.

It’s not all bad. The best jokes in the short book are at the Tribune’s expense, satires of its obstinate isolationism and eccentric conservatism under the Colonel in competition with the Sun-Times’s vivid tabloid sensibility. A better editor than cartoonist, Hef understood the lay of the local media landscape. And much of it remains pretty timeless—even if the Viagra Triangle, the setting for many of his jokes, has since gone from seamy to slick under the cultural influence of his magazine.

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