The sexual revolution pretty much started in the basement ‘grotto’ of this 1899 mansion. Chicago magazine impresario Hugh Hefner bought it in 1959 and dubbed it the first Playboy Mansion, even hanging a brass plate over the door warning ‘If You Don’t Swing, Don’t Ring’. Alas, Chicago became too square for Hef by the mid ‘70s, so he split and built a new Playboy Mansion in LA.
And that's where he remains today, in his pajamas. After he left, he donated the State St building to the School of the Art Institute for a dorm (imagine the pick-up lines!). It was gutted in 1993 and turned into four very respectable, very expensive condos. Hef's company, Playboy Enterprises, stayed headquartered in Chicago until 2012, and then it too moved west. The last vestige is ‘Honorary Hugh M Hefner Way’, which is what the city renamed Walton St (at Michigan Ave) in an official tip of the hat to Hef.
