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The Big Party

FROM JULY 2009: After launching the Playboy empire here in the 1950s, Hugh Hefner turned Chicago into a frontline of the sexual revolution, acting out his sybaritic fantasy life behind the walls of his mansion on North State Parkway. But as the freewheeling sixties gave way to the decadent seventies, things changed drastically for Hefner and the Gold Coast mansion he called home

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Hugh Hefner, in Paris in 1970, with his then-girlfriend Barbi Benton and the movie director Roman Polanski
Hefner, in Paris in 1970, with his then-girlfriend Barbi Benton and the movie director Roman Polanski Photo Gallery »

Hefner has always enjoyed a deeply romantic streak, and when he first saw the grand manor at 1340 North State in the winter of 1959, he fell hard. “He loved it,” recalls his friend and colleague Victor Lownes. “It met his needs perfectly.”

At the time, Hefner had achieved a measure of fame, both on the strength of his racy, daring new magazine and his up-by-the-bootstraps story—a Chicago boy hocks his furniture to start a magazine that makes him wildly rich and puts him at the forefront of one of the most powerful cultural movements of the century: the sexual revolution. All of this in a rust-belt city under the sway of its newly crowned potentate—da’ mayor—Richard J. Daley, a national political player, but a buttoned-up old-school square who banished underlings who fell short of his deeply Catholic, almost fusty sense of propriety. But it wasn’t until the publisher started throwing his parties at 1340 North State that Hefner became an icon.

Built in 1899 for a prominent Chicago doctor named George Isham, the 72-room mansion had been one of the famed residences of its day, having entertained such guests as Theodore Roosevelt. Guarded by imposing wrought iron fences, the brick and stone structure offered spectacular possibilities for a newly crowned King of Pleasure, starting with a 60-foot-long, 30-foot-wide ballroom large enough to accommodate hundreds of guests, a giant marble fireplace, inlaid teak floors, oak-paneled walls, a grand staircase, and bronze chandeliers. The basement offered the perfect location for the indoor pool Hefner had dreamed of having, with an adjoining garage where he could store his custom-built Mercedes convertible.

Hefner snapped up the mansion for $400,000, then quickly sank hundreds of thousands more into renovations. Within months, he had constructed a sybaritic paradise that was part salon, part Roman bath, part fortress, and part show-palace, all two blocks from Lake Michigan and a bunny hop from the teeming bars of Division Street. In addition to the kidney-shaped tropical pool, which featured a “woo grotto” reached by plunging through a cascading waterfall, the house included a game room, an underwater bar reached via fireman’s pole, a bowling alley, a steam room, a tanning room, and a descending movie screen installed in the ballroom on which guests could take in first-run flicks. Two suits of armor guarded the entrance and a museum’s worth of original artwork adorned the walls, including a huge Picasso over the fireplace.

Hefner scans photos shot for Playboy in 1961
Hefner scans photos shot for Playboy in 1961 Photo Gallery »

Upstairs were lavish guest suites nicknamed the Blue Room and the Red Room—sleeping accommodations for honored guests—and double rooms reserved as dorm space for 25 to 30 Bunnies at the soon-to-be-opened Playboy Club. A fleet of butlers and a fully staffed kitchen catered to the whims of Hefner and his guests, who could order off of an extensive room service menu around the clock. And then there was Hefner’s bedroom, which featured plush white carpet, a Jacuzzi large enough for 12, and, most famously, an enormous rotating round bed fitted out with buttons with which Hefner could control the television, stereo, and lights.

The finishing touch was a gift from Hefner’s associate publisher, A. C. Spectorsky, a brass plaque bearing the Latin phrase Si Non Oscillas, Noli Tintinnare. Attached to the front door, its English translation provided a cheeky warning, as well as a credo for both house and master: “If You Don’t Swing, Don’t Ring.”

Previously, you might have found Hefner prowling the Rush Street triangle in the wee hours—nightclubs like Cloister on Rush, or the Black Orchid, or The Chez Paree. In those pre-mansion days, he would make the rounds with an after-hours band of brothers: Shel Silverstein, the bald, bearded Chicago cartoonist; Don Adams, the comedian who would gain renown as the star of the television comedy Get Smart; and Victor Lownes, the suave, womanizing impresario of the Playboy Clubs—number two man at Playboy, and one of Hefner’s closest friends. Once ensconced at 1340, however, Hefner found few reasons to venture out.

Before Chicago could catch its breath, Hefner had bought a second building, a five-story living embodiment of the Playboy lifestyle that would create an equal stir and generate an even greater amount of publicity. The Playboy Club at 116 East Walton Street was patterned after an elegant members-only Chicago establishment called the Gaslight Club, where patrons were served by beautiful showgirl waitresses dressed in abbreviated costumes. Playboy magazine had run a small feature on the Gaslight and the response was astounding. “When I saw that reaction, we felt we had something much larger,” says Lownes, who was made director of promotions for the Chicago club, and who would eventually become lord of a vast network of Playboy clubs across the United States and abroad.


Photography: (top) Michael Lipchitz/Associated Press, (bottom) George Brich/Associated Press


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