The Sexy History of Hugh Hefner’s Playboy Mansion

There are many iconic properties around the world that have stood the test of time, but none is as unique or as enticing as the massive estate located at 10236 Charing Cross Road in Los Angeles, most commonly know as the Playboy Mansion.

A few decades ago, Hugh Hefner’s pleasure palace was widely known as one of the country’s most notorious party homes, with everyone from celebrities to lusting teenagers yearning for an invitation to party alongside Hef’s bunnies.

Now, its wild party days are long behind it, but the home continues its tradition of entertaining guests, and is now a sough-after setting for Hollywood events and fundraisers. 

Though the provocative appeal of the Playboy Mansion might have died down over the years, and especially after Hefner’s passing in 2017, it continues to fascinate. There’s no other place like it in the world. It’s become an iconic staple in Los Angeles, and the embodiment of the glamour and decadent lifestyle of the rich and famous. 

Despite its notoriety, the Playboy Mansion might still hold some untold secrets. We’re going to bring you up to speed with all the things that you should know about this iconic mansion. Beware, some of the things we’re about to tackle are not for the faint of heart.

The original Playboy Mansion 

Some of you might be surprised to learn that the massive estate in Los Angeles is not the first Playboy Mansion that Hugh Hefner has owned. In fact, Playboy Magazine used to be headquartered in Chicago in the 1950s and 1960s.

Hugh Hefner bought the 70-room, 30,000-square-foot mansion at 1340 North State Parkway in Chicago’s Gold Coast District in 1959. This property served as the original Playboy Mansion — and it also featured the original ‘grotto’ in the basement, which included a swimming pool and an attached bar, perfect for parties. 

The house also featured an ‘inviting’ message on the front door, which said ‘If you don’t swing, you don’t ring.’ That should give you an idea of what went on inside Hefner’s Chicago home.

There was also a bowling alley, a game room, bedrooms for Hefner’s Chicago Playboy Club Bunnies, and apartments occupied by close friends or employees. Fun fact: one of the doors from the original Playboy Mansion is now in Michael Jordan’s house (and it’s one of the basketball player’s most treasured collectibles).

Bobbie Arnstein, Hefner’s assistant and close friend, also lived at the mansion. She was later convicted on drug charges in 1974 and sentenced to 15 years in prison, but ended up committing suicide in 1975. The media frenzy that came with the trial forced Hefner to leave Chicago and move to Los Angeles, where he would live until his death 43 years later. 

The priciest home sale in Los Angeles history, at the time

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