Hugh Hefner had a plethora of bizarre rules his girlfriends were under strict instructions to follow - including what colour their hair had to be, what time they should be inside the Playboy Mansion by, and prohibiting the women from speaking to his employees.
American publisher Hefner, who died in September 2017, founded men’s lifestyle and entertainment magazine Playboy in December 1953.
The Illinois native, who was worth an estimated $43million when he died, fuelled media interest by sharing a luxury mansion and embarking on relationships with multiple women, one of which was 45-year-old Holly Madison - a woman who was once described as his ‘number one girlfriend’.
The star, who previously lived at the Californian property with the star,, has recently opened up about what was expected of herself and other models at the mansion.
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Speaking about sleeping with Hef, Madison told the In Your Dreams podcast host Owen Thiele that he expected his girlfriends to perform ‘disgusting’ sex acts.
"Well, it's a very different story between when we were just by ourselves than with everybody else in the room," she told the 28-year-old Theatre Camp actor.
“Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it.
“If it was just me and him, it was a lot more normal than you would think.”
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Interestingly, staging group sex sessions wasn’t the only rule that Hefner would impose on his girlfriends.
The golden rule was monogamy… at least for Hefner’s girlfriends
It’s widely understood that Hefner would often have multiple girlfriends on the go at once.
However, while the pensioner was allowed to embark on various relationships, he allegedly expected his lovers to remain exclusively faithful to him and him alone.
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In her 2015 memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Madison wrote: "While Hef could date an entire sorority house full of girls, we were to remain totally loyal.”
Another of the editor’s former girlfriends, Izabelle St. James, 49, previously explained how ‘weird’ it was to be part of a group dating the same guy.
“He created his own world, his own fantasy where he set his own rules. And I wanted to learn more,” she revealed.
One colour lipstick was banned from the mansion
Henfer was reportedly extremely strict and often controlled what his girlfriends could and could not wear, including banning a particular colour of lipstick from the mansion.
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“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.”
The Oregon-native explained that the business mogul believed wearing red lipstick was a choice made by ‘older mature woman’ and that he wanted his playmates to remain ‘very young and fresh-faced’.
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Platinum blonde hair was paramount
It wasn’t just lipstick shades that Hefner allegedly took issue with; it was hair color too.
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Madison claimed during an interview on the 2021 Power: Hugh Hefner podcast that if you were cast as one of the father-of-four’s girlfriends, then you were required to have blonde hair.
“You were expected to look a certain way,” she confirmed.
Some of the most famous blonde playmates include Bridget Marquardt, Hefner’s third wife Crystal, and even Blondie’s Debbie Harry.
Speaking about dying her hair, Crystal told People last year that she’d routinely have ‘blisters’ on her scalp from the practice.
Abide by the curfew
According to St. James, Hefner had a strict 9pm curfew in place for all of his girlfriends due to fears of them cheating on him if they were out late.
"We had to be home by 9pm," she once 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.”
Former Playboy model Jenna Bentley once told the Daily Mail that if you missed the strict curfew, you’d be made to sleep on the lawn.
Sign on the dotted line
Bentley once told the Daily Mail that she’d signed an ‘iron-clad’ NDA so she wouldn’t be able to reveal what she saw going on behind closed doors at the Playboy mansion.
However, Crystal has previously claimed that she was not subjected to signing any legislation during her relationship and subsequent marriage with Hugh.
Christmas was to be spent in the mansion
Girlfriends residing at the California mansion were allegedly unable to return home for Christmas, according to Madison’s memoir.
“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," she wrote
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."
Residents must relinquish their former homes
Not only were Playboy models banned from spending Christmas outside of the mansion walls, but they were also reportedly expected to give up their previous homes.
“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,” Madison said on the Power: Hugh Hefner podcast.
Some of the girls famously lived in the house rent-free, while others paid for their rooms.
Payday often came with some repercussions
In her 2006 memoir, Bunny Tales: Behind Closed Doors at the Playboy Mansion, St. James claimed that collecting weekly wages and allowances from Hefner was somewhat difficult.
“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."
The Ninja Cheerleaders actress also claimed the businessman would use the intimate opportunity to air any grievances with his girlfriends, including complaining about ‘the lack of harmony’ among them.
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.”
There was a ban on drugs
Hefner’s dislike of illicit substances has been well documented.
He even went as far as to state in his will that any of his heirs would be blocked from receiving their inheritance if they became ‘physically or psychologically dependent on drugs or alcohol’.
It’s said that alongside his family, the media tycoon banned his girlfriends from taking drugs or becoming dependent on alcohol too.
No ‘mingling’ with the staff was allowed
The Playboy Mansion, which consisted of 29 rooms, reportedly needed around 80 full-time staff members to remain fully operational.
These included landscapers, butlers, cleaners, and more who Hefner’s girlfriends were allegedly forbidden from canoodling with.
"You weren't supposed to be hanging out with the butlers,” said St. James.
Meanwhile, Madison 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."
Topics: Celebrity, Hugh Hefner, Sex and Relationships, US News
Ella Scott