Playboy, a men’s lifestyle and entertainment classic, in terms of prominent magazines and more, was a huge success in the industry. This was because Hugh Hefner had the money and a dream, he knew could be his reality. The success of his dream transformed him into a sexual liberation advocate and an activist, by which he became a public figure. This just mentioned, suggests that the magazine wasn’t the only notable thing about Hugh Hefner. His brand was an opportunity for many women, those known as Playboy Playmates, and a guarantee to them of a prosperous career. You could imagine how anxious people were to be featured in his publication.
After moving to Los Angeles, that which began in Chicago earlier on, now exhibited a more lavish glamor, as Hefner gave an explicit definition to the word “partying.” Sexual freedom had found herself at the epicenter of Hefner’s world, and it was always celebrity-filled. The Mansion’s party was a ballroom event, and you’d easily expect to share the atmosphere with the likes of Joe DiMaggio, Dean Martin, and Warren Beatty. Anyone would kill to have such an experience. But more to that, and still referencing Jay Gatsby, people longed to satisfy their starving curiosities and speculations about all that transpired behind her curtains and, better still, were ready to spill their discoveries to the public.
Disbelief shows on the faces of people when they’re told Hefner laid his foundations in Chicago. He purchased his mansion in the Windy City in 1959 for $400,000. The city became home to the Playboy Towers Hotel, the Playboy Theatre, and a 1000-acre resort with 300 rooms.
He allegedly became a public icon when he began his lavish parties at 1340 North State Parkway. With other notables discovering the existence of Hugh Marston Hefner, he was soon lured to where he belonged, Los Angeles, California. He bought the Mansion there and resumed his legacy in the prestigious city of LA.
The Feds conducted stings at the Playboy Mansion in Chicago that almost caused its downfall. The Mansion there got caught up in a scandal where, allegedly, illegal substances made their way with ease within the Mansion. Yet, the government couldn’t get enough to pin Hefner, so they attempted to get him by way of an associate, his assistant, Bobbie Arnstein, and a man she was involved with, Ron Scharf. In desperation, the FBI and DEA reportedly forced from her a testimony against her boss, pressuring her against her will.
Either she was threatened by her boss, or maybe she was sincere about her boss’s innocence. Either way, it was clear she had no intention of selling out her boss. This left her with only one line of action: she checked into a hotel room and took her own life. It brought a tragic end to the narcotics drama and halted the Federal pursuit against her boss. It might have in fact acted as a catalyst for the Chicago departure of Hefner and his brand.
A confusing, yet to-be-accepted fact about the Mansion was that when it was purchased, and though Hefner was the founder and most acquainted with the Mansion, the purchase wasn’t done in Hefner’s name, rather the company’s, a purchase in 1971 from Louis D. Statham.
The reason why it wasn’t bought in his name is quite unclear; he paid $100 annually as a residence fee to Playboy, the brand. His reason for this will never be known given his death.
Not everyone could afford the Mansion party, as it was one thing to first be invited to the party, following Hefner’s giving a go-ahead (as the coordinator of invitations), and it was another thing to buy the tickets. If you weren’t covered under his umbrella of good grace, hope offered no chance for your entry to the party.
Provided you were considered important enough to be invited as a guest, you had to have enough financial means to pay your way to get in. His lists of invitees were quite exclusive. Further, if you made it to this sacred yet lavishing event, you had now better be on your best behavior. If you were not, you earned a badge of banishment for as long as Hefner desired.
Basically, as an invitee to the Mansion, it meant you as a person were important and that however lavish the party was that was being thrown, a certain behavior was expected of you. Though the Mansion represented an enormous amount of freedom, Hugh’s strict foot never wavered.
On one occasion, Luke Wilson, attending as a guest, claimed to a staff member that he was accompanied by a person said to be his brother, Owen Wilson. But instead, he came with a friend. The lie found its way directly to Hefner’s ears leading to Wilson’s 18 months of banishment from the Playboy Mansion. This was a significant punishment, and it was a clear message to every guest. NFL star, Reggie Bush, also got blacklisted and banished for violations of conduct.
The Playboy Mansion, off-limits to the average person, hosted a bunch of notable celebrities and quite often. One of those was Elvis Presley, some years before his death. Presley at the peak of his career in the 1970s gained an invitation to the Mansion.
Whether or not he was banned after a claim of some sort of Mansion misconduct is known for sure, but about that night spent at the Mansion, rumors soared that he was cozying up to eight different women, during and after the party. In the room, which is named after him, the rumor says they got real down and dirty. Then it was nicknamed the “Elvis Suite” and locked off from prying eyes.
Following the numerous rumors that flooded about concerning the atmosphere of the Mansion and the lavish gist of her parties, people, even celebrities, were dying to have that experience. The average attendees hardly saw the grand entrances of noble celebrities who made it inside, but they did see them at the party. Rumors soon took off again that for the fear of being blacklisted as an infidel, or found with illegal substances, or to avoid the plentiful paparazzi, celebrities had for themselves a secret tunnel that gained them entrance without any buzz or notice.
There were even unverified rumors of tunnels that led to their individual homes which were located nearby. Celebrities like Jack Nicholson and Warren Beatty were victims of these claims which satisfied the public’s curiosity and speculation. However, Hefner revealed to the general public that such claims, the printed pictures that seemed to show accesses, and blueprints that circulated, were nothing but myths.
Men like Hefner suffered none when it came to attracting women. He had everything they needed. With the women not having money, Hefner had the ability to smelt rocks into shining stars. Over the years, the Playboy brand never ran out of Playmates. These women were not intimate with him, though. There existed a clear explicit distinction between those who modeled as Playmates for the brand and those who were intimate with him.
The second group of women were his girlfriends, and it is in fact known that he had in his roster as many as 12 girlfriends at a time. The number of people struggling for his attention, to gain success, might have been a distraction to the Playboy founder, but Hefner saw no difficulty. The Playboy brand is a living testimony to his agility.
People perceived to be living according to the norms of society usually connect with persons of the same age, and of course some prefer those a little younger or a bit older than them. Such was not the case with Hefner’s girls—all who dated him were decades younger than him.
It would be difficult to avoid stereotyping them as gold diggers, since the reality is that they did date him for the money and fame. Carla Howe, for instance, compares her relationship with Hugh to being with a granddad.
As one of the exclusive residences in Los Angeles, it was a natural instinct to figure that the gates, of massive size, were mounted at the entrance to keep strangers at bay. But your instincts come to nothing upon meeting Hefner’s main girlfriend.
Holly Madison, in her book, wrote that, on the contrary, the big gates were mounted to keep her and the others in. According to her say, she and some of the Mansion’s other residents were prisoners because they had grown weary of the place, but the gates served as an unmovable barrier and prevented their exit.
Hugh Hefner had a one-sided relationship with the women. His freedom and theirs were inversely proportionate. For instance, while he was allowed to engage and consort with as many ladies a possible, the women were strictly forbidden from similar relationships with any other men.
Karissa Shannon spoke more about this with Popeater, saying she had to leave the premises of the Mansion as she was forbidden from bringing men. Hefner, however, allowed them to entertain men he chose—presumably his guests—but nothing could happen between them. They were to stay faithful with him throughout.
It’s shocking how with the fame and fortune that they enjoyed; the ladies mostly had nothing but ill experiences during their stay at the Mansion. Some of them spoke of this ill experience Hefner put them through.
With the strict curfew of 9 pm, Carla Howe, speaking with The Mirror, claims that they suffered consequences if they arrived at the Mansion later than 9 pm. They had no choice but to do as he requested.
Of the many perks for these women, one was unique and also compulsory. To last a long time in the role of being Hefner’s girlfriend, you could only earn money from Playboy. Their only pay came from the company. They couldn’t model for anybody else at all. The gates were open to them in this respect; the earning potential was present. They felt the money and fame were worth it.
This exclusivity made them more indebted and dependent on him. And one of the schemes he used to get them to “do all it took to please him” was that he’d then make more public appearances with them.
This is a two-part ceremony if you must know. The first part was something a majority of the women found unnecessary. For instance, Izabella St. James in her book shared her pure detest for the ceremony. It included going to Hefner’s bedroom on Friday mornings for their $1000 allowance. He gave it to them in $100 bills, counting it in front of them. Moreover, if any of the girls broke any rules that week, she couldn’t receive her allowance for that week.
The second part, however, was his discussing his innermost dissatisfaction with the ladies. According to Izabella, he frequently complained about the tension between the women—women who just became of age, all trying to get the attention of a 78-year-old man, to paint a clearer picture of what was going on. He constantly charged them to be better than their previous behaviors.
With the countless number of rules and regulations choking the Mansion’s atmosphere, it’s inevitable that someone will do something wrong or misbehave in some way. Each time the girlfriends knew they had fallen out of line; it was because they had received an email that was intended to keep them on track.
As soon as they had in their inbox something from Hugh, things were probably about to be unpleasant. Even when it was unconscious, what they might have done, he kept them conscious and aware with their email inboxes. Little things like them not looking their best prompted another new message in their inbox. As a girlfriend of Hefner, you had no choice except for perfection.
A loose chain in the Mansion strictness that was so pervasive was the fact that the women were permitted to decorate their rooms according to their tastes. However, whatever they desired to do in this area was a product of their own time and money.
It’s a relief to know the women, in their years spent there, were allowed to make their room their own. One of the girls, however, was not so positive. Izabella recalls the “disgusting” state of the mattresses. Even if they had the freedom to choose their flavor, it’s disturbing to know they never had comfort when their eyes were closed for a night of rest.
The residence without the parties could sometimes be synonymous with the silence of a graveyard. According to Kendra Wilkinson, days went by without crossing paths with the gentleman. Hefner had his alone time, shocking right? It actually shouldn’t be, given the Mansion’s strict rules and the adherence to them by the girlfriends.
Kendra claims she only met him sometimes at his office, at an event, or when there were scheduled intimate dates. It appeared Hefner didn’t fancy one-on-one dates, to go elsewhere. So the residents had little to keep themselves occupied with during the general time.
Intimate moments were an anxiously awaited time for the women, as they all always looked forward to it. A pause for possible disappointment is necessary, before you’re let it on this one, however… Intimate moments came with their own set of rules too.
Whenever Hefner longed for fun, he lay on his bed after intoxicating himself with some substances. His girlfriends were given two minutes, with each making the most of her limited time. Those who weren’t involved in the intimacy cheered each other on, making things more entertaining for Hefner.
Illegal substances were known to be present at his LA residence. Over the years, rumors spread that narcotics were in use at the parties, and it affected the roles the girlfriends played at each party as well.
The founder of Playboy reportedly suggested this use was to “give [them] a nice buzz” during private nights they had together. According to Izabella, and other girlfriends, they were encouraged to take the narcotics to ensure their mood was in a right space for Hefner, and only Hefner. It’s quiet disturbing, if it’s indeed true.
If you’ve been reading along, rituals and rules shouldn’t shock you anymore. To summarize the endgame: it made Hefner the master, the one and only in control of his own created game. This sacred ritual involved the ladies taking a bath and putting on a specific pair of pink flannel pajamas.
Jill Ann Spaulding lets us in with more details in the book she wrote, showing the readiness of the ladies for what was ahead. Whether they enjoyed it all, they only know. To maintain their residence in the Playboy Mansion, they had to do all Hefner wanted.
Hugh Hefner had occupied himself with sets of unequal beings, and certainly one standout had to lead this pack of inequality. Holly Madison, during her time there, had the privilege to occupy this position, though without actually being above the house law. Still, she had the privileges the other women constantly envied. It made it difficult for Madison to have a genuine friendship with the others.
Given the number of women Hefner had in his harem, and his desire to be intimate with all, it was not easy. The absence of medical attention and Hefner’s old age made it difficult for his wishes to be fulfilled. To achieve a smoother fulfillment, he had to spread out schedules of time spent with each girlfriend. According to Jill Ann Spaulding, his main girlfriend—Holly Madison—was always the first to go upstairs with him.
Dating a man of 78 years at 18 couldn’t be seen as pedophilic as she was of age. Though a 60-year gap spaced their lives, the two managed to entangle intimately. It wasn’t quite the atmosphere for young Kendra, who was full of exuberance, and Hefner, who was intoxicated with his rules and regulations.
Young Kendra struggling to get along with the Playboy founder found some mutuality, as Hefner had his own struggle with her. He pitched to Kendra the idea of hitting a gym, as to his eyes she “looked a little bigger.” The comments messed with her self-esteem as a young woman and as someone who took it as a serious job to please him. She constantly compared herself with the other women because she believed she wasn’t slim enough. It’s a relief she’s out of this emotional jail.
Differences in opinions, character, and values coming all together in one single residence made fighting occurrences inevitable. With the ground rules set by Hefner, the women still would have found it hard to control their tempers, and indeed arguments ensued, as reported by guests at the Mansion.
Some reasons for the outburst were when Hefner promoted one ahead of the other as his main girlfriend (of the moment). But, also, catty fights burst open at the parties, between boxing ladies with no interest but entertainment.
One additional interesting fact you should know about Hefner was his fondness for animals and pets. He kept all sorts of animals at the Playboy Mansion, with inclusions of some exotic pets. Many of the dogs in the residence came from girlfriends, though.
Despite the unsafe atmosphere of the Mansion, some exotic animals managed to live out the rest of their lives in its environment.
The Mansion gave a new definition to partying, and every time there was one at the Playboy Mansion, there was no repetition of events. No two parties were ever the same. The out-of-control nature of the parties was probably the most famous trait of all.
Some parties went completely bananas. For instance, a llama passed away at one of the parties. The cause of death was unknown, but it prompted the authorities to remove a large percentage of the Mansion’s creatures. At another event, John Lennon left a burnt hole from a cigarette on an authentic Henri Matisse painting.
Stephen Baldwin and Robert Downey Jr. were each invited as a guest to the Mansion, and Baldwin recalled in his autobiography a piece of information when the two went to the basement.
Downey warned him to be careful with one of the steps as it housed an alarm from the times of prohibition that alerted within the house. There is need for more solid evidence, though, before believing it all.
A mansion isn’t a mansion without a pool. Playboy’s Mansion wasn’t an exception. Right by the water was the most packed place of all, with activities at every party over the many years.
In 2011, there were 200 guests who suffered from legionnaires from a bacteria lurking in a whirlpool hot spa on the premises. The LA County municipal department in charge investigated in a proper manner and then handled the cases of illness.
Towards the end of Hefner’s life, the excellent condition of the Mansion took a turn for the worse as the Mansion fell into a pit of despair. The remaining animals made it worse.
Asides from that decay, according to Izabella, the Mansion was “stuck in the ‘80s.” A multitude of people agreed with her and suggested the Mansion needed an urgent refurbishing.
Considering in detail the life of Hefner, there was nothing boring that found its way into his life’s history and overall legacy. During his time on earth, he employed someone whose job was to scrapbook everything about “Hefner” that could be assembled.
Starting from his childhood, through the founding of the Playboy brand, and down to his final days, everything about him, including his obituary, made it to the scrapbook. Nothing about him had an excuse to be forgotten.
Given the iconic imagery and impact of the Playboy Mansion on the city of Los Angeles, it was odd to imagine somebody else owning it. But Hefner wasn’t immortal, and he passed away in 2017. Society would expect him to give the large Playboy Mansion home to his heir, and at 90, he was still being contrary. He found a buyer in 2016.
He sold the Playboy Mansion to his next-door neighbor Daren Metropoulos for $100 million. Daren however couldn’t do anything in the building as the ruler laid down a rule of doing nothing till his death. So far, it could be said that Hefner spent his final years in a building that wasn’t the Playboy Mansion anymore.