15 Secrets Hugh Hefner Took With Him To The Grave

We have only tidbits of information, but out of these pieces, we can form a picture of what Hefner was really like behind the closed doors.

The world is reeling after the loss of Hugh Hefner, who was best known for founding Playboy Magazine. He was 91 years of age when he passed away, and he died of natural causes. Not only did he live a long life, but he lived 91 years of a lifestyle most of us can only dream of. He had the money, he had the mansion, and he definitely had the girls. But Hugh Hefner also had secrets, and a lot of them. There was always something a little shady about the Playboy Mansion, and I guess that was part of the appeal for most people. Hefner was always seen as someone who challenged the status quo, and was one of the most important people to change the way we view human desire. Before Hefner, a magazine like Playboy would've been seen as completely scandalous. Today, the age-old publication seems almost mainstream.

There are many things we still don't know about this mega-rich player, and I guess we'll never know some of the secrets this man carried with him. Because like many old men who have lived a life full of wild parties and controversy, he took a lot of his biggest secrets with him to the grave. We have only tidbits of information to feed on, but out of these pieces, we can form a picture of what Hefner was really like, behind the closed doors of the famous Playboy Mansion.

15 The Mansion Was “Like Prison”

Many think the Playboy Mansion was a luxurious and happy place where girls got to live a carefree lifestyle. But that just wasn't the case. Although Hefner made sure that the public image of both himself and the girls around him looked fun and wild, he was actually extremely strict with his girlfriends. This is a secret not many people know about the Playboy mansion, and it sheds a dark light on this famous playboy's legacy. When you hear what some of the girls had to say about their time at the Mansion, it sounds more like slavery than a consensual relationship.

Carla Howe revealed that living at the mansion as one of Hefner's girlfriends was "like being in prison." She confessed that "when you’re here you have to be in by the 9pm curfew. You’re not allowed to invite any friends up to see you. You’re definitely not allowed male visitors. If you break the rules you get banned. Once you’re out, you’re out, and you can’t come back."

14 The Mansion Wasn't As Glamorous As You Think


When people think about the Playboy mansion, they conjure up images of the most glamorous palace imaginable, complete with every luxury anyone could want. And the images we see of this mansion definitely back up this idea. Lots of gold, beautiful architecture, and huge pools typify this amazing house that has become so well-known. But was it really what it was cracked up to be? Some girls have come forth to tell one of Hefner's most tightly-kept secrets: the famous Playboy Mansion was actually a complete wreck, and many of its rooms were filthy, and far from luxurious.

Izabella St. James revealed that “'each ­bedroom had mismatched, random pieces of furniture. It was as if someone had gone to a charity shop and bought the basics for each room. Although we all did our best to decorate our rooms and make them homely, the mattresses on our beds were ­disgusting—old, worn and stained. The sheets were past their best, too."

13 He Wasn’t The Player You Think He Was


Hugh Hefner had quite the reputation as a lady's man. In fact, you could say he was the ultimate "player." He was known for his many girlfriends, and the fact that even in his old age, he would still sleep with these much younger women. But as many of the girls have revealed, he wasn't that all that great:

Crystal Harris revealed that intimate moments with Hefner did not "last" very long, and she was not really excited by him. She also revealed that Hefner never bared it all.

Holly Madison also revealed that Hefner was far from romantic: "There was zero intimacy involved. No kissing, nothing. It was so brief that I can't even recall what it felt like beyond having a heavy body on top of mine."

12 Kendra Wilkinson Cheated On Hefner Repeatedly


Hefner was known for being a very possessive man when it comes to his relationships. This was why he was so strict about enforcing a curfew, and the girls knew this. He also was reportedly very strict about the way his girls behave at parties. During these events, his girlfriends were expected to sit with him at his table for the entirety of the party. They were supposedly only allowed to leave the table to go to the bathroom. And they were strictly forbidden from interacting with the men and celebrities who frequented the mansion.

That's why Hugh Hefner never wanted anyone to know the truth about his relationship with one of his closest girlfriends, Kendra Wilkinson. She admitted that she cheated on him repeatedly while she was living at the mansion. She says she used to rent motel rooms close to the mansion in order to meet her love interests. Kendra admitted: "I had respect by not going public with any of my relationships. I never hooked up with anyone in the mansion while being with Hef."

11 If You Wanted To Live In The Mansion, You Had To "Get With" With Hefner

While Hugh Hefner never explicitly revealed this to the public, no girl got to live at the Playboy mansion for free. While he didn't charge them a cent to stay at this famous house, they were expected to pay in other ways... Pretty much every girl has gone public and mentioned that in order to stay at the mansion with Hefner, you had to sleep with him. What would usually happen, according to many of these former Playboy girls, is that Hugh Hefner would ask one (or two, or three) of the girls to upstairs with him, and "that was that." Girls have stated that pretty much nobody enjoyed these "sessions" with Hefner, and they put up with it in order to be part of his lavish lifestyle.

They also mentioned that girls were expected to sleep with Hefner before they moved into the mansion, as sort of an "initiation." This paints Hefner in a very different light, and some would even say this amounts to abuse. Obviously it's very important that someone never feels pressured into intimate relations. Is there any truth to these rumors? I guess that's a secret Hefner will take to his grave.

10 His Sons Are Pretty Weird


While Hugh Hefner made sure that everyone could see how many beautiful women were hanging off him, he was a little more guarded about his family life. His sons did not take as much of the spotlight as he did, and it's a good thing too. By many accounts, they were not the sort of people who would be suited to the celebrity life. The eldest of his sons, Cooper, was described by many of the Playboy girls as "shy" and "kind of a geek." Definitely not the sort of heir you would expect to inherit the Playboy mansion. But behind the geeky, awkward demeanor, there's a wild side to this guy as well. He married a famous actress and then encouraged her to pose for Playboy magazine. He also fought hard against the decision to remove photos that "bare it all" from the magazine, saying that it went against everything his father stood for.

Marston Hefner, the younger son, isn't the ideal heir either. He has been charged with physically assaulting his girlfriend, something he pleaded "no contest" to. You have to wonder whether Hugh Hefner's hedonistic and misogynistic lifestyle had an impact on his sons' psychological well-being. In Marston's case especially, it's hard not to wonder whether Hugh's objectification of women made the younger son feel like it was okay to hurt women.

9 He Gave His Girlfriends Questionable Substances


Hefner was also known to be quite the prescription drug enthusiast. He would also routinely offer, and in some cases pressure, his girls into taking prescription drugs. One girl recounted a time when Hefner offered her a quaalude (a type of barbiturate) in a scrunched up napkin. But perhaps the drug Hefner was best known for was male enhancement medication. According to many sources, he popped this medication "like skittles," and, by many accounts, was addicted to it. Some even say that his overuse of it lead to his hearing loss.

What does Hefner say to accusations that he offered his girls prescription drugs? "Over the course of my life, I've had more than my fair share of romantic relationships with wonderful women," Hugh said in an interview. "Many moved on to live happy, healthy, and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can't win 'em all!"

8 Sometimes His Girlfriends Shared The Same Room As Hefner’s 9-Year-Old Sons


As Hefner began to age, he started to make some pretty bizarre choices. It's unclear whether this was just due to his natural, quirky personality or the frailty of his elderly mind. But one thing's for sure, there are some strange decisions that this man made that he never expected people to learn about. Many of these secrets he will in fact take to the grave. But although he never revealed any of these secrets, Hefner's girls are coming forward and telling the truth.

Holly Madison revealed that due to a shortage of rooms in the mansion, some of the girls were expected to share bedrooms with Hefner's 9 and 10-year-old sons. Although they would take turns using the room, and never slept in the room together, there's no denying how creepy this is. Holly Madison revealed in her book: "Though they never stayed over when I was there, there were still toys scattered across the bedroom floor, which made for an incredibly odd and, frankly, creepy juxtaposition."

7 He Would Routinely Body-Shame His Girlfriends


Hefner was a man with very particular tastes, and if you were one of his girlfriends, then you better make sure your appearances catered to this man's preferences. Judging by the types of women that surrounded him, it was easy to see what his "type" was. Blonde hair, large implants, and a pretty face. But the minute a girl started to drift from this "ideal" look, Hugh Hefner would be the first to tell you about it. Girls who were at the mansion reveal that they were under immense pressure to look as perfect as possible, and the circumstances could be dire.

When the girls got dressed up to go out or to have a party at the mansion, Hugh Hefner's staff took pictures of all the girls. He would then drop these pictures by their doors in the morning. The idea was to show the girls how they looked, and allow them to see any of their imperfections. The girls were also told point black that they had been gaining weight, needed plastic surgery, or had started to "let themselves go."

6 He Told Them To Dress As Trashy As Possible


Hugh Hefner was celebrated by some as being one of the key figures to normalize s*xuality. He was a big part of the s*xual revolution that took part decades ago. Due to people like Hugh Hefner, people started to realize that natural desires were nothing to be ashamed of, and started to be more free and open with them. Whether this was a good or bad thing is open to interpretation. But while Hugh Hefner is a hero for the "free love" movement, he's an enemy of another kind of revolution: feminism. Hugh Hefner had a tendency to treat women like objects–even ordering them what to wear. Hugh Hefner took another secret to his grave: that he was possibly the biggest misogynist ever.

And as Holly Madison reveals, these outfits were not meant to be fashionable, respectable, or tasteful: "He made it abundantly clear that he preferred us in very over-the-top, sort of trashy outfits (think bedazzled rhinestone bustiers and skirts so short there was barely a point in wearing them)."

5 The Girls Were Not Paid Very Well At All - By The End They Were Paid Nothing


So if Hugh Hefner was such a controlling, patriarchal figure, then why did women sign up to be his Playboy bunny girlfriends? The answer is simple and obvious, and I'm sure you can already guess; they did it for the money. There are numerous stories of girls moving in with Hefner and doing whatever he asked them to do for the simple reason that they wanted to be paid handsomely. Some women have revealed that they were struggling financially as models, or they needed to pay off cosmetic surgery bills.

But Kendra Wilkinson tells a very different story. She's one of the more recent girlfriends of Hugh Hefner, and she revealed that she wasn't paid a cent. She only did it because she wanted to move out of her terrible, tiny apartment. This is another secret that Hugh Hefner tried to take to his grave. He wasn't even paying his girls anymore. Room and board was all they got by the end. They also didn’t get paid for the reality TV shows they starred in, and they made about the same as an amateur model from their photoshoots.

4 Some Girls Developed Depression From Staying At The Mansion


After what you've heard so far about how Hugh Hefner's girlfriends were treated in the Playboy Mansion, it should come as no surprise that many of these women developed serious cases of depression. It was just such a fake and threatening situation to be in, and many girls even contemplated suic*de. One of these girls was Holly Madison, who wrote in her tell-all book about the time she found herself crouching in the Playboy mansion bathroom, sobbing and trying to figure out how she was going to take her own life. This same woman was also treated for depression and prescribed anti-depressants while she was living at the mansion.

Cassandra Lynn-Hensley was another former Playboy model who left the mansion with an unstable state of mind. This girl was not as lucky as Holly Madison–she died at the age of 34 after an apparent overdose of drugs and champagne. She was found in a bathtub. Whether this was accidental or intentional, we do not know. But what's clear is that Cassandra's drug use came after a long stint at the Playboy mansion, so maybe she turned to substance abuse as a way to self-medicate from her psychological trauma suffered at the mansion.

3 Rumors Of Illegitimate Children


For a man like Hugh Hefner, it should come as no surprise that there are countless rumors about him fathering illegitimate children. When your life revolves around hooking up with countless young women, mistakes are bound to be made. I'm sure there are many children around the world right now who are related to Hugh Hefner, and have no idea about the truth. This is perhaps one of the secrets Hugh Hefner really did take to his grave, as I'm sure deep down he knew of the various illegitimate children he fathered. He may have even paid some of the mothers to keep quiet, or visited their children in secret.

One example of a illegitimate son fathered by Hugh that went public was the case of Mark Wilson. In 1984, Hefner revealed to the world that he did have an illegitimate son, and that he would accept him as his own. But not long after, this was determined to be false with the help of a DNA test. Still, the fact that Hefner readily believed he was the father of this man shows how careless he was being at the time. Perhaps one of the biggest secrets Hugh Hefner took to the grave was the secret knowledge that he had irrevocably hurt so many women.

2 Playboy Magazine Was Losing Money Before Hefner’s Death

Another thing that Hugh Hefner probably didn't want the world to know about was the fact that his business wasn't actually doing that well when he passed. It's a well-known fact that Playboy Magazine was going through somewhat of an identity crisis in the past few years, and this undoubtedly led to the controversial and milestone decision to remove photos that reveal it all from the magazine recently. This was obviously a response to slumping sales, and an effort to try and appeal to a wider market.

The internet is another factor that probably contributed to the decline of Playboy Magazine in recent decades. Although Playboy did expand to an online presence, it wasn't enough to stop the virtual impact on this famous magazine. Put simply, if someone wants to see revealing photos of women, they don't need to buy magazines like Playboy anymore. They can just employ the use of a simple Google search query. Perhaps one of Hefner's greatest secrets is that he died as a man with a rather unsuccessful business.

1 He Never Revealed Who He Wanted As His Heir

Taking into account what we've just mentioned, the decision of who will inherit the Hefner throne isn't that big of a deal. In fact, of the people in line to inherit his business, many might see it as a dangerous thing. After all, with the magazine's sales steadily dropping, the person who takes the reigns would be expected to somehow turn things around and make Playboy back into the household name that it once was. But for that to happen, Hugh Hefner would've had to name a successor, which he didn't.

There is no doubt that Hefner lived like a king; he was maybe an overly promiscuous king, but a king nonetheless. He sat on a throne, surrounded by women a quarter of his age, in a mansion that seemed like it was dreamt up by a teenage boy. But every king knows that naming a successor is a big part of royalty. This is something that Hefner failed to do. Whether this was because he believed he would never die, or he just never got around to it, we will never know. This is another secret Hefner took to his grave...


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15 Secrets Hugh Hefner Took With Him To The Grave