Hugh Hefner’s Chicago

In 1951, Hugh Hefner was a fresh college dropout living with his parents in suburban Galewood. By day he worked in Chicago as a copywriter for Esquire and started his publishing career with “That Toddlin’ Town.” It’s a collection of cartoons not unlike the ones in The New Yorker (which is satirized on one page).

You can find the whole book at that wonderful treasure trove The Internet Archive, but here are some highlights:


“We’re listening to the music. What d’ya think we’re doing?”
(if I’m being nitpicky, the angle shown of the Petrillo Bandshell wouldn’t have the city behind it)


“The Colonel’s in a helluva mood! Little Orphan Annie got off a comment in this morning’s edition that could easily be construed as pro-Democrat!”

Col. Robert McCormick, who published the Chicago Tribune looked like a cartoon in real life (see his appearance on the cover of Time). His views got even more out of date as he got older. One of his opponents called him “the greatest mind of the fourteenth century,” all the more fitting for a man who spent his days in a gothic tower.

All the more fitting that four days after McCormick’s death, Richard J. Daley would be elected Mayor of Chicago for the first of six times.



“Do you think demanding a clean-up is a very good idea when it’s me who’s running for re-election?”
What’s worse is that people who run for office calling for things to be cleaned up usually lose.



“She’s outa step with the music.”

She’s doing the Rita Hayworth “Put the Blame on Mame” glove pulling tease. Rita did it with a dress on and nobody complained.


“I ain’t advocatin’ nothin’, lady. I’m just a little guy that’s tired of lookin’ up at people all the time.”

The Bug House Square debates still happen once a year, courtesy of the Newberry Library, where anybody can get up on a soap box and sound off about whatever they want. In the old days people were a lot more lively in responding to speakers, and while they encourage liveliness at the debates today, everybody’s real nice (unless you talk about Israel).


“How do you expect to attract any business serving a lousy drink like this?!”

The man in this one looks a lot like A. J. Liebling, the writer for the New Yorker who stayed in town for a year, then wrote The Second City, which has this passage:

A thing about Chicago that impressed me from the hour I got there was the saloons. New York bars operate on the principle that you want a drink or you wouldn’t be there. If you’re civil and don’t mind waiting, they will sell you one when they get around to it. Chicago bars assume that nobody likes liquor, and that to induce the customers to purchase even a minute quantity, they have to provide a show.

Liebling obviously didn’t take well to the beers in Chicago (even though most of them were made in Wisconsin).

Hefner got fired from Esquire in 1952 after they wouldn’t give him a raise. He raised $8,000 in capital, including a $1,000 loan from his mother, and the first issue of Playboy went to press in December 1953.

Recent Posts