Before dying at the age of 91 back in 2017, Hugh Hefner made a name for himself as the founder and editor-in-chief of Playboy magazine before expanding his empire into a multi-million dollar industry.
He infamously hosted weekly depraved sex parties, became the subject of a number of sexual assault allegations and, amidst throughout the course of his many scandals, Hugh also mapped out a seriously grim, yet extremely strict, set of rules for any of the housemates living in the notorious Playboy mansion.
So, without further ado, let's get into all the ins and outs of what really went down behind the gilded doors at Hugh's sprawling residence, which his former girlfriends lived at for free.
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However, that's not to say they didn't pay a price...
Strict curfew
According to Izabella St. James, one of Hugh's former girlfriends, Hugh called for all housemates to be back at the mansion by no latter than the watershed.
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"We had to be home by 9pm," she told Fox News Digital, "Hef didn't want girls to go out and party without him. I suppose he didn't want us to have the opportunity to be unfaithful."
One-way monogamy
Despite Hugh having multiple girlfriends at any given time, it's clear his partners weren't afforded the same privilege, so much so that one of the late pensioner's strictest rules was that his housemates had to remain completely faithful to him, even while he was sleeping with several people.
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"I’m not going to pretend or lie - it was very weird to be part of a group of seven girlfriends dating the same guy," St. James revealed. "He created his own world, his own fantasy where he set his own rules. And I wanted to learn more."
She added: "I thought his whole world was just fascinating."
In her 2015 memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Hugh's 'main' girlfriend, Holly Madison, confirmed: "While Hef could date an entire sorority house full of girls, we were to remain totally loyal."
Mandatory orgies
Speaking to BuzzFeed News a decade back in 2015, Madison shared that the prolific sex parties always took place on the same two days of the week.
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"It was always Wednesdays and Fridays after the club. It was always exactly the same because that's just how he likes to live his life," she said.
According to Madison, all of Hugh's girlfriends were required to take part as she explained: "They knew it was kind of a quote-unquote requirement for living there, and expected.
"And it had kind of a chore vibe, I felt."
And as for what went down before the orgies took place?
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Well, St. James said during an episode of A&E's Secrets of Playboy: "Girls all shower or take a bath. And people sit on his bed. Then he would smoke a joint, and girls would pop champagne bottles and order food."
Playboy model, Zoe Gregory, also claimed that Hugh would take Viagra before having sex with all seven of the girlfriends he had at the time, spending roughly one minute with each of them.
"But when you're doing that, a minute feels like five," she recounted.
No fraternising with the staff
The Playboy models were also reportedly forbidden from fraternising with the staff who worked at the 29-room mansion with St. James telling Fox News Digital: "There was no mingling with the staff.
"You weren't supposed to be hanging out with the butlers."
Madison confirmed the rule as she wrote in her memoir: "The girls were not allowed to 'fraternise' with the staff unless absolutely necessary.
"This rule was not to be taken lightly. Hef would totally lose it if he caught one of us talking with anybody on the service team."
No brunettes allowed
It becomes immediately apparent that Hugh had a type when it came to choosing his girlfriends.
Namely, long locks of platinum blonde hair.
And the housemates' similar 'dos were far from a coincidence as, during an appearance on the Power: Hugh Hefner podcast in 2021, Madison confirmed: "You were expected to look a certain way obviously, you had to have the blonde hair."
In her memoir, Madison recounted just how brutal Hugh could be if he didn't like one of the housemates' haircuts too as she found herself on the receiving end of his wrath after debuting a cute bob cut one day.
"I came back with short hair, and he flipped out on me. And said it made me look old, hard, and cheap," she shared, noting that his remarks went on to haunt her for years.
No red lippy
The control went beyond hair too as Hugh also had rules on what make-up his girlfriends could or couldn't wear.
"Among the many unspoken rules at the mansion, the red lipstick rule was one of the more notorious," Madison wrote in her memoir. "I'm not over-exaggerating here.
"Hef absolutely despised red lipstick and wouldn't allow his girlfriends to wear the colour."
She found this out the hard way after rocking a red lip only to be ordered: "Don't ever wear red lipstick again."
Detailing the rule, Madison also said on the Ahead of the Curve with Coco Mocoe podcast: "I think he didn't love it because when he invented the concept of a playmate in the '50s, he wanted the women to look very young and fresh-faced."
She continued: "He felt like the look in the ‘50s at the time was very - he described it as somebody's older sister, explaining what he didn't like.
"He wanted skimpy and fresh-faced and very young looking."
She went on to explain that to Hugh, red lipstick was a choice made by 'older mature women', which put him off as it wasn't 'the barely legal thing anymore'.
Pay day
As we know, Hugh's girlfriends were allowed to live in the Playboy Mansion rent-free.
Additionally, they were given a weekly allowance but it seems that collecting the dough was far from a glamorous affair.
In her 2006 memoir Bunny Tales: Behind Closed Doors at the Playboy Mansion, St. James explained: "We had to go to Hef's room, wait while he picked up all the dog poo off the carpet - and then ask for our allowance.
"We all hated this process."
As if the extremely demeaning, and frankly beyond grim, process wasn't bad enough - it also came with a side of Hugh's criticism towards the women, sort of like a performance review.
"Hef would always use the occasion to bring up anything he wasn't happy about in the relationship," she wrote. "Most of the complaints were about the lack of harmony among the girlfriends - or your lack of sexual participation in the 'parties' he held in his bedroom."
St. James also claimed: "If we'd been out of town for any reason and missed one of the official 'going out' nights he wouldn't want to give us the allowance. He used it as a weapon."
It's clear Hugh couldn't stand any criticism of his lack of sexual prowess as Crystal Hefner, the widow of the late Playboy founder, said in her 2024 Only Say Good Things: Surviving Playboy and Finding Myself memoir: "[Hugh] seemed less sex-savvy than some of the teenage boys I’d been with years ago.
"It was clear to me Hef had never taken a moment in his entire life to figure out how to please someone else."
No other home
Hugh's girlfriends were also reportedly expected to give up their previous homes when moving into the mansion.
Speaking on the Power: Hugh Hefner podcast in 2021, Madison explained: "You weren't allowed to have an apartment of your own, which while I lived there, there were some women who did, they just kept that a secret from him."
No drug policy (kind of)
The Playboy housemates were also reportedly banned from taking drugs - although, it appears as if this rule was bent on quite a few occasions.
"The climate inside the mansion was toxic. I didn't participate in the cocaine benders, the side boyfriends, or all their harebrained money making schemes that were all in direct violation of Hef's house rules," Madison wrote in her memoir.
With that said, however, in A&E's Secrets of Playboy, another one of Hugh's former girlfriends suggested that he actually did partake in hard drugs from time to time, saying: "Hef pretended he wasn't involved in any hard drug use at the mansion, but that was just a lie.
"It was such a seduction, and the men knew this - that they could get girls to do just about anything they wanted if they gave them a quaalude."
Christmas
Christmas spent away from Hugh was apparently off-limits for his girlfriends as he reportedly insisted that all his partners spent the occasion with him rather than family members.
"Girlfriends were given 'off' days before or after the holiday to visit family and friends, but there were no exceptions for the actual day itself," Madison revealed in her memoir.
She added: "That was the one house rule that no one seemed to mind, because Christmas was when Hef was most generous with his girlfriends."
NDA galore
Following Hugh's death in 2017, a number of his ex-girlfriends have started coming forward to share their experiences of what went down at the Playboy Mansion with some discussion on the use of non-disclosure agreements (NDAs).
However, Crystal revealed that she never signed one during her relationship with Hugh.
Topics: Celebrity, Hugh Hefner, Playboy, Explained, US News, Sex and Relationships
Rhiannon Ingle