For many of the Playboy bunnies it’s the end of an era as the Playboy Mansion has been sold and the King of the throne is now married and behaving himself. Or is he? We decided to uncover some of the most shocking moments, unforgettable parties and sex scandals that rocked Hugh Hefner’s world and the girls around him.
You see, we can’t help but wonder who the man is behind the velvet robe and what will become of the Playboy Empire and all the sex scandals and shocking secrets that come with it. If you’re anything like us you just want to uncover some of the most outrageous moments and live vicariously through the Playboy bunnies living life in the mansion with secrets untold.
Well that wait is finally over and you can put your dirty imaginations to bed as we reveal Hugh’s most shocking moments including sex, drugs and breaking headlines. We stalked the social media pages of bunnies old and new for clues, spent hours looking through the interwebs and even read an autobiography or two so we can deliver you this exclusive report. Sure, you’ve watched the TV show and watched the lives of the live-in girlfriends unfold, but did you know about Hugh Hefner’s set of House Rules or the 9pm curfew he imposed upon the Bunnies? We bet you’ve heard about the VIP mansion’s parties and its A-List celebrity-filled guest list, but did you know Bill Cosby allegedly committed one of his sex crimes behind those very walls?
Sure, the house is filled with half-naked girls and alcohol- it’s Playboy, after all- but we bet you didn’t know Hugh Hefner has a penchant for Quaaludes? If you fancy hearing more, and we know you do, check out our top 15 Hugh Hefner shocking moments revealed now.
15. The Time He Allegedly Tried To Drug Holly Madison
Life at the Playboy Mansion wasn’t anything like what was depicted in The Girls Next Door E! reality show and we have proof straight from the horse’s mouth. Or in this case, former Playboy bunny Holly Madison’s mouth. She dished the dirt on what it was really like to live in the Playboy Mansion when the cameras stopped rolling and it was lights out for the girlfriends. You can read all about her life of sin as she detailed her days in the mansion in a second memoir entitled The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention.
She isn’t one to hold back and even went so far as to reveal that despite Hugh’s image to the world as a ladies man it was certainly not the case when it came to their intimate relationship. She revealed they had only been intimate once! And to think that’s not even the worse part… Our dear Hef offered Holly a crumpled tissue containing a Quaalude the very first night they went out clubbing. Hef’s take on the situation is even more disturbing as he simply commented: “Usually I don’t approve of drugs, but you know, in the ’70s they used to call these pills ‘thigh openers.'”
14. Hugh Hefner’s Thoughts On Party Life
Alright so you now know of Hugh’s love of Quaaludes so chances are you could probably see this coming from a mile away – his little blue pill collection. It seems almost ironic that the Playboy founder himself needs a little assistance in the follow through. He may be a successful businessman but how successful is he between the sheets in the moments that matter most? The Chicago native once revealed his thoughts on sex and his playboy lifestyle to his own Playboy magazine saying: “The notion that Playboy turns women into sex objects is ridiculous. Women are sex objects. If women weren’t sex objects, there wouldn’t be another generation. It’s the attraction between the sexes that makes the world go ’round. That’s why women wear lipstick and short skirts.”
13. His Little Bedroom Tray
We have it on good authority that living in the Playboy mansion wasn’t anything like you would expect it to be and for former Playmate Izabella it wasn’t even the least bit glamorous. We decided to find out more and after browsing the pages of her tell-all autobiography Bunny Tales: Behind Closed Doors at the Playboy Mansion we can’t help but sympathize after the shocking revelations.
Here you’ll find old, dirty bedding and mattresses and odd broken furniture within the rooms of the Playboy mansion. White carpets that are no longer white thanks to the bunnies’ dogs using the floors as their own personal bathroom outlet.
Still not too shocked? Wait until you learn about his little bedroom trays… All was revealed from E! reality show Girls Next Door’s cast member and former girlfriend Holly Madison. She revealed in detail in her latest memoir that one of the mansion character items was a little tray. It contained Johnson’s Baby Oil, Vaseline, and Kleenex and these trays could be found in every bathroom as well as in the grotto, the tennis courts and even the pool bar.
12. Hugh Is An Avid Scrapbooker
So Mr. Hefner likes to indulge in an afternoon or two of scrapbooking. That doesn’t sound too shocking but what if we were to tell you he enjoys it more than sex? The Playboy founder has a rumoured collection of over 2,485 volumes of scrapbooks. Perhaps his budding obsession was born out of his desire to avoid the press and to preserve all his memoirs in his own way. After all, it’s no secret that Hugh is not a fan of conversation and interviews with members of the press.
Okay, we’ll admit it may just be a tiny bit impressive as he has spent over ten years perfecting his collection and preserving his memoirs. He has never once faltered in his scrapbooking ways which detail almost every aspect of his colourful life.
Some of the pics that can be seen in his collection even include a copy of the famous nude Marilyn Monroe photo that graced the first issue of Playboy. That memorable issue sold over 54,000 copies. Another page in the scrapbook includes press clippings featuring the death of former Playmate of the Year Dorothy Stratten. She was tragically shot to death in 1980 by her husband at the time, Paul Snider.
11. Hugh Enforced A 9pm Curfew
So just to put things into perspective for all of you- drugs are allowed, sex is encouraged and nudity is a given but late nights are a big no-no in the Playboy mansion. We kid you not as we discovered that our dear old Hugh actually put a 9pm curfew in place. The Playboy founder demanded his girlfriends adhere to the early night curfew and let’s just say it wasn’t received too well by the bunnies. Former girlfriend and author of Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Holly Madison expressed her views and was anything but a fan of the idea.
She revealed that her former boyfriend used to kick his feet, cry a few crocodile tears and even threaten the girls. She went on to say that “he told us if they wanted to ‘stay out late’ they could move out. Everyone had to be on the Mansion grounds by 9pm every night unless we were out with Hef at a club or a function. People honestly did not believe us when we told them we had a curfew.”
10. He Prefers Pajamas Over Lingerie
It’s no secret that there are countless rules and rituals that are firmly in place when it comes to the Playboy Mansion. But it’s alarming to think that the playboy himself prefers pajamas over lingerie and after what we discovered it seems that this may just be the case after all. Another fun fact that you didn’t know is that Hugh liked all his girlfriends to be dressed in identical pajamas. Pink flannel pajamas to be exact.
All was revealed when a daring blonde took pen to paper and expressed what really went down between the walls of the mansion. Former Playmate Jill Ann Spaulding published a tell-all book entitled Jill Ann: Upstairs which certainly got the world’s attention. Jill revealed: “On sex night you go upstairs and the girls that are brand new, or the girls who don’t have their own room yet, have to take a bath. That’s a requirement. You also have to put on a certain pair of pink pajamas. They’re all lined up and neat. You can tell they’ve been to the cleaners. They tell you to put them on, even though you take them off as soon as you enter Hef’s room.”
9. The Playboy Mansion Daily Schedule
“Sex is the driving force on the planet. We should embrace it, not see it as the enemy” says Playboy founder Hugh Hefner. Something tells us however that sex is not the enemy here but rather a strict schedule enforced by Hugh himself. If you went about your days thinking life in the Playboy mansion was all kinds of spontaneous and glamorous then you’d be wrong. One of the playmates revealed exactly what went on behind closed doors and it was anything but spontaneous and free. Playmate Izabella St. James depicted her time at the mansion in an autobiography and revealed exactly what Hugh’s daily schedule entailed:
Fun-In-The-Sun Sundays- A pool party and screening a new release in the Mansion movie theatre
Manly-Night Mondays- Hef’s friends came over for dinner and cards
Family-Night Tuesdays- Hef’s ex-wife and sons came over
Club-Night Wednesdays- Clubbing and then coming home for Hef’s bizarre sex rituals
Off-Night Thursdays- No planned activities
Club-Night Fridays- A repeat of Wednesday’s activities
8. Discovering Hugh’s Bedroom Is One Big Mess
Trust us, we were just as surprised as you were to discover that Hugh Hefner’s room is a mess. And sure we could just say it’s untidy, but rumour has it that it has surpassed the untidy stage and moved straight past into unholy mess territory.
In Izabella St. James memoir she went on to say that “even basic hygiene is a concept Hugh Hefner is yet to grasp.” Ouch. Then again, we did hear the sordid details about dirty carpets, broken furniture and the little bedroom trays so perhaps we shouldn’t be as shocked, right? It is believed that Hugh Hefner wasn’t too fazed by dirty carpets and the one he has in his bedroom hasn’t been replaced in years. Add former girlfriend Holly Madison, who stayed with Hugh in his room with her two dogs, and things became even worse. Did we mention that the little hounds weren’t house-trained and just added to the dirty state of the carpets?
7. Hugh Hefner & Bill Cosby
Just when you think you couldn’t possibly learn something new relating to the Bill Cosby scandal, Hugh Hefner’s name is dropped into the mix. It’s no secret that the rise and fall of everybody’s favourite TV dad Bill Cosby caught us all by surprise. But now it’s been alleged that he allegedly molested a 15-year-old at the Playboy Mansion and that some of his other sexual assaults on women took place in the mansion itself!
Chloe Goin has boldly accused Hugh Hefner of allowing Bill Cosby to unknowingly drug underage women during several of his Playboy Mansion parties. The Playboy founder responded by saying he had no knowledge of or involvement in Cosby’s alleged behavior at the Mansion and that her claims were unfounded. The LAPD has since decided to not go forward with criminal charges against Hugh Hefner.
6. Hugh’s Group Naughty Rituals
Hugh Hefner runs a tight ship and when it comes to the girls living in the Playboy mansion every rule, schedule and habit is approved by the man himself. If you’re anything like us though, and are curious to find out more about what goes on behind closed doors, then we have just the answer for you. After years and years of playing the guessing game, a few ex-girlfriends have delivered all the answers, finally revealing everything. In her tell-all book former girlfriend to the Playboy king Holly Madison writes: “I didn’t immediately realize that all girlfriends were required to sleep with Hef. Hef’s group of girlfriends stood around the bed insinuating girl-on-girl action whilst Hugh proceeded to smoke a joint. Each girl then has a quick turn with him. It was so brief that I can’t even recall that it felt like beyond having a heavy body on top of mine” Holly writes.
5. Hugh Banned Side Boyfriends
As far as monogamous relationships go, you’re usually never allowed to have a side boyfriend or girlfriend. But what about when things aren’t so monogamous and say you’re Hugh Hefner living with anywhere between three to 15 girls at any one time? Well, you’ll be surprised to hear he likes to keep things traditional as well.
“We were not allowed to have boys in the house. That was the absolute number one rule. No boys allowed. That was one of the main reasons we moved out” said former Playmate and girlfriend Karissa Shannon in an interview with PopEater magazine. In her book, Holly Madison added, “Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in.”
4. Hugh’s Kids Lived With His Girlfriend
Apparently kids stay for free at the Playboy mansion but it’s at the price of his girlfriends. If you were hoping to hear all the sordid details of the mansion and the daily lives of the Playboy bunnies then you have come to the right place. Coming in at number four on the list is the fact that Hugh Hefner’s kids also stayed at the Playboy Mansion and more shocking is the fact that they shared a room with one of his former girlfriends.
We discovered that lo and behold Hugh’s sons Marston, who was aged nine at the time and ten-year-old Cooper, shared a bedroom with ex-Playmate turned girlfriend Holly Madison when she first moved in. Things only changed when she became his number one girlfriend and went on to move into the main bedroom with Hugh. Holly had been previously allocated to “Bedroom Three” which included three beds in total and a private bath. Holly revealed “Though they never stayed over when I was there, there were still toys scattered across the bedroom floor.”
3. Hef Gave His Girlfriends An Allowance
What would you say if we were to tell you that Hugh Hefner paid his girlfriends a weekly allowance of $1,000 a week? Just when we thought we had heard it all our dear Hugh surprises us once more. The girls had an account at the Jose Eber Salon in Beverly Hills which they visited when building their clothing wardrobe. They weren’t forced to spend the money entirely on clothes but let’s just say saving the allowance or using it to pay off say student loans was frowned upon.
Former playmate and housemate Izabella St. James revealed all in her controversial tell-all: “Every Friday morning 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: a thousand dollars counted out in crisp hundred-dollar bills from a safe in one of his bookcases. We all hated this process. Hef would always use the occasion to bring up anything he wasn’t happy about in the relationship. 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. If we’d been out of town for any reason and missed one of the official ‘going out’ nights [when Hefner liked to parade his girls at nightclubs] he wouldn’t want to give us the allowance. He used it as a weapon.”
2. Hefner Has Experimented With Homosexuality
Coming in hot at number two on our exclusive featuring 15 Hugh Hefner shocking moments revealed is the revelation that the Playboy founder has dabbled in homosexuality in the past. Sure he is a well-known playboy, successful businessman and Chicago native but there are other sides to the former World War II veteran that we knew absolutely nothing about, until now. The Richest is all about lifting the lid on scandals and revealing secrets untold. The story goes that one late night in Chicago, a man offered to give Hugh Hefner fellatio, and never being one to turn down anything in matters of the bedroom, he agreed. Perhaps it should come as no surprise after his candid interview with Esquire Online back in 2013- one where he expressed his views on sexual expression:
“If you don’t encourage healthy sexual expression in public, you get unhealthy sexual expression in private. If you attempt to suppress sex in books, magazines, movies and even everyday conversation, you aren’t helping to make sex more private, just more hidden. You’re keeping sex in the dark. What we’ve tried to do is turn on the lights”
1. He Doesn’t Know How Many Women He’s Slept With
After all that is said and done Hugh Hefner has admitted that he doesn’t really know how many women he’s slept with but he imagines it to be around the 2,000 mark. “Beauty is everywhere on the campus, in the office, living next door. Nice girls like sex too, it’s a natural part of life. Don’t be ashamed of it.” says Hugh. By the sounds of things our dear Mr Hefner isn’t ashamed of much…
He has also said: “Life is too short to be living somebody else’s dream. I have no plans to retire. It’s the perfect combination of work and play that keeps you young. If I quit work it would be the beginning of the end for me. Follow your own particular dreams. We are handed a life by peers, parents and society, you can do that or follow your own dreams. Life is short, be a dreamer but be a practical person.”
Even if he had a lot of shocking secrets we’ve now revealed, remember, Hugh once revealed to CNN that he is like a kid in a candy store: “I dreamed impossible dreams. And the dreams turned out beyond anything I could possibly imagine. You know, from my point of view, I’m the luckiest cat on the planet.”