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A History of Hugh Hefner in Chicago

By Elizabeth Tieri on January 18, 2013


Most locals remember that, like Hugh Hefner himself, the myth and image of Playboy was born here in Chicago. But standard trivia like that is never enough for us! So let’s take a moment to talk a little more about the story behind the man and his club. You can learn a bit more by joining our Historic Chicago Walking Bar Tour, of course.

Hugh Hefner: Most Famous Chicagoan?

First and foremost – yes! Hugh Hefner is originally from Chicago. In the 2010 documentary about him, he says, “My roots come from Chicago. My dreams came from Hollywood.” He was born and raised by conservative Midwestern Methodist parents in Montclare, a neighborhood on Chicago’s northwest border. After earning a psychology degree from the University of Illinois at Urbana Champaign in less than three years, probably with the help of his 152 IQ score, he came back to the city and lived and worked here for many years before moving to LA in the ’70s.

First Foray in PublishingHugh Hefner in Chicago That Toodln' Town

Hefner’s first dabble in–what we’ll call–adult publishing was released shortly after returning to Chicago from school.  That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals was released in 1951. Though the title says quite a lot, it does not say it all. This little book (that you can read online) is a compilation of comics that play off of Chicago scenes and people with some of the sophistication, sexiness, and silliness that we associate with Hefner’s other endeavors.

A few years later, during a sort of winter of his discontent, Hefner sold most of his belongings and started work on what would become the first issue of Playboy. From there, he launched a worldwide enterprise involving not just publications but also all kinds of entertainment and activism in censorship.

Chicago Sex History Playboy Hugh Hefner in Chicago

Playboy Conquers the World

Success and prosperity ensue. Hefner buys himself a mansion in the Gold Coast, where he can enjoy whatever he pleases. And if you doubt that for a even a second, just consider the famous plate above the doorbell that read, “Si Non Oscillas, Noli Tintinnare” in Latin. In English it means, “If you don’t swing, don’t ring.”

Then on leap day in 1960, Hefner opened the first of the Playboy Clubs at 116 E. Walton St.. Here “keyholders” could come to eat and to drink while enjoying big name entertainment and service from ladies dressed as Playboy Bunnies.

Hugh Hefner in Chicago Playboy sign Palmolive BuildingAfter a few years, they move to the Palmolive Building at 919 N. Michigan Avenue, where they topped the building with nine-foot-tall letters declaring their presence.

The Playboy Legacy in Chicago

Nowadays, Hugh Hefner is so often associated with his plethora of lovers and escapades that we tend to overlook the role he played in politics and philanthropy. This man was constantly defending his First Amendment Right to the freedom of speech. Hefner battled segregation by hiring African American women as Bunnies. He also advocated tolerance of sexual preferences, including homosexuality, with the stories he published in his magazine and his lifestyle. He considered this a part of his sexual revolution to challenge the more Puritanical media of the times. Hefner even has a subspecies of Marsh rabbit named after him for his support against their endangerment.

Though Hefner left Chicago for L.A. in the ’70s, he kept the Playboy offices here in Chicago until just last year. We know that Hefner was sad to see the move happen, and so were we.  Still not satisfied? Consider viewing Playboy artifacts at the Chicago History Museum. Or learn more on the Historic Chicago Walking Bar Tour.

— Elizabeth Tieri, Chicago Detours Tour Guide


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


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