Dirty Confessions: 15 Things That Happened At Hugh Hefner's Mansion

For decades, the Playboy Mansion has been the place-to-be for Hollywood partygoers. The parties held at the mansion were invite-only, giving people a level of exclusivity and a feeling that they were part of the 'in' crowd. One poor outfit choice, one bad joke, one awkward interaction with a Playmate, and you might find yourself getting blacklisted from the mansion.

Over the years, the Playboy brand has become quieter and quieter. This could due to poor sales for Playboy magazine, or it could be attributed to the fact that the old man who's the face of Playboy, Hugh Hefner, is 91 years old. Many Playmates and former girlfriends of Hefner have told reporters that he doesn't enjoy partying. Instead, he prefers to have a quiet movie night with friends and his multiple girlfriends. Though the Playboy era may be coming to an end, it had a number of glory days.

Due to the nature of Playboy and the types of people that the Mansion attracted, you would expect there to be a number of insane stories that happened at the Mansion. And there are. In fact, here are 15 of the craziest things that happened at the Playboy Mansion. These stories come from former Playmates, former girlfriends of Hefner's, and even Hefner himself. Not only will these stories give you an inside look into the Playboy party lifestyle, but you'll also learn that life at the Playboy Mansion isn't anything like you thought it would be.


15 It Was A Home Away From Home For Hollywood A-Listers

For some of Hollywood's hottest stars, partying at the Playboy Mansion was a given. Hooking up with supermodels becomes exponentially easier when you're an attractive movie star at the height of your career. Some of these men include Colin Farrell, who loved to have sex outdoors, and Owen Wilson, who's apparently incredible in bed during group sessions. Even Frankie Muniz spent a bit of time at the Mansion, missing out on his own prom to attend a party there!

Of course, many years ago, Jack Nicholson, Warren Beatty, Kirk Douglas, and James Caan practically lived at the mansion. In fact, James Caan actually lived at the Playboy Mansion while he was trying to get over a divorce. He ended up moving out after he started fearing that he would be unable to enter the real world again if he stayed at the Mansion for too long. There was a rumor circulating (now debunked) that some of the regulars had an underground tunnel built to connect their houses to the Mansion!

For the men who nearly lived at the Mansion, their bachelor lifestyles never seemed to leave them. Jack Nicholson, now 80 years of age, says that although he has slept with over 2,000 women in his life, his playboy reputation hindered his love life. He said he yearns for one last romance.

Will Leonardo DiCaprio feel similarly at 80 years of age?

14 Hugh Hefner Has S-x With 10 Women At A Time


At 91 years of age, you have to wonder exactly how many women Hugh Hefner has slept with. He's known for flaunting a number of girlfriends at a time as arm candy but claims that he's always been faithful when he's been married. That said, he claims he makes up for it when he's single, and he's sure he's had sex with over a thousand women.

In 2004, former Playboy bunny Jill Ann Spaulding revealed a number of sex secrets about Hugh Hefner in her tell-all book, Jill Ann: Upstairs.

One of these secrets is how Hefner is able to have sex with so many women in a single night. To start, he takes Viagra to help him perform in the bedroom because, at his age, it's probably impossible to make it happen naturally. Next, Hefner lays on the bed, and each girl takes a turn having sex with him for 1-2 minutes at a time before letting the next girl have a go. The sex is completely unprotected, and according to Jill Ann Spaulding, neither Hugh or the girls are ever tested because he simply doesn't care.

But is it really a secret that Hugh Hefner has orgies with Playmates? Didn't we all just assume that happened?

13 John Lennon Was Almost Beaten Up Over A Cigarette

In 1974, John Lennon was invited to the Playboy Mansion by Hugh Hefner on a Sunday afternoon to watch movies and enjoy a buffet with Hefner and his friends. The afternoon was somewhat unpleasant, as Lennon arrived acting very off. In interviews, Hefner stated that Lennon had drunk too much and was under a tremendous amount of pressure.

According to Hefner, Lennon, in sort of a weird-spirited prank, decided to put out his cigarette on one of the paintings in the mansion. The painting Lennon chose was a priceless painting by Henri Matisse, whose work had, in the past, sold for over $15 million at auctions.

Friends of Hefner wanted to rough Lennon up because of his little practical joke, but Hefner decided to let it go, saying he was a huge fan of Lennon's. After all, it was just a painting, right? Then again — if someone you invited over for a movie night put you $15 million in the hole, would you forgive him? What if it was John Lennon?

12 Bill Cosby Punched Tommy Smothers


Bill Cosby's reputation has been completely ruined in the past few years — but for most of his career, he was one of the most respected comedians to come out of the 1970s. Today, however, he's known as a creepy old man.

In 1977, Bill Cosby and comedian Tommy Smothers were both attending a party at the Playboy Mansion. Smothers, who had become a hardcore political activist after his show The Smothers Brothers Comedy Hour had been canceled took it upon himself to confront Cosby about his lack of protest about the Vietnam War. Smothers felt that Cosby should've been taking a more public stance on civil right issues.

After calling out Cosby, Smothers complemented Cosby's show, saying, "It was a really good effort." Cosby, thinking that Smothers was being condescending, chose not to respond. Smothers responded to Cosby's silence by saying, "Well, f*** you," and walked away.

According to witnesses, Cosby was so filled with rage that he couldn't control himself. He walked behind Smothers and punched him in the back of the head, knocking him to the ground, then began to berate him. Hefner stepped between the two men to break up the would-be fight.

People who had worked with Cosby were not surprised by his violent outbreak. Apparently, Cosby had trouble controlling his anger behind the scenes of his television shows.

11 Leonardo DiCaprio Loves To Have S*x Outdoors

Leonardo DiCaprio has lived an extraordinary life. His career started at an early age, appearing in television commercials and soap operas, but he really found commercial success in the movie What's Eating Gilbert Grape. From there, he hit back-to-back-to-back home runs, starring in The Basketball DiariesRomeo + Juliet, and Titanic, which was the highest-grossing film of all time until Avatar claimed that title in 2009. Very few movies starring Leonardo DiCaprio are bad, but that could be because he frequently stars in films directed by Martin Scorsese, a filmmaker in a league of his own.

DiCaprio, very openly, lives a bachelor lifestyle. When he isn't trying to save the Earth's environment or filming his latest movie, he's usually seen on yachts with supermodels from around the world. His taste for supermodels may have developed when he began spending nearly all of his downtime at the Playboy mansion.

According to former Playmate Izabella St. James, DiCaprio could click his fingers and take his pick of any girl he wanted. He was often seen taking 5 or 6 girls from the mansion to his house. Women who slept with DiCaprio bragged that he loved to sneak around the property and have sex next to the monkey enclosures.

10 Dita Von Teese Martini Dance


Dita Von Teese is a modern-day burlesque dancer and entered the mainstream spotlight while dating shock rocker Marilyn Manson. For those that don't know, burlesque dancing is comparable to a classy strip tease. Von Teese is one of the most well-known burlesque entertainers. Her best-known performance is a striptease around a giant martini glass, with her routine ending when she gets into the glass and douses her naked body with water.

Von Teese had posed for Playboy a number of times before she was put on the cover of the magazine for the first time in 2002. In 2003, she was invited to perform her martini dance at the Playboy mansion during the Dewar's 12 Playboy Lounge Tour.

If you've seen the routine (you can find it on YouTube), you'd believe that her routine is the sexiest thing to ever happen at the Playboy mansion. That's how good she is at what she does.

9 The Hot Tub Made 200 People Sick

While attending a two-day partying and networking conference, part of which took place at the Playboy Mansion, 200 attendees became sick unexpectedly with flu-like symptoms. Medical officials believed that the partygoers were infected by Legionella pneumophila — a bacterium that flourishes in warm, wet, environments, like a hot tub, for example.

Now, it's not completely uncommon for people to experience mild flu-like symptoms after coming into contact with Legionella pneumophila, but what the partygoers were experiencing was much more severe than anything doctors had seen before. The origin of the outbreak was not initially known, but investigators have said that the hot tub in The Grotto at the Playboy Mansion is most likely to blame.

The Grotto is a hot tub inside an artificial cave that was once the highlight of the mansion. It was romantic, secluded, somewhat hidden, and allowed guests to have a little extra fun during parties at the Playboy Mansion. Though this disease outbreak happened in 2011, the fact that there was an outbreak at all put The Grotto in a negative light. What was once a romantic getaway quickly became viewed as a trashy hot tub where you'll be lucky to not contract something after getting wet.


8 The Elvis Room


Often referred to as the "Elvis Van/Room" is a room that's designed to look like the back of a 1970s van. The floor is one large mattress, the walls and ceiling are made of mirrors, and a few 1970s-styled pillows are used to decorate the bed. When getting a tour of the mansion, a number of people reported that their tour guide said that the room was built for napping. Yeah, okay.

The room is sometimes connected to Elvis Presley because of what allegedly happened in it. According to Playboy legend, Elvis Presley once 'slept' with eight Playboy bunnies at the same time.

Today, the Van Room is mostly hidden from the public. Maybe the room is used for too much 'napping' lately, or maybe, the mattress in the room has become so stained with shame that it's been deemed unfit for the public.

7 Luke Wilson Was Banned For A Year

Luke Wilson — who's pretty much known for being the brother of Owen Wilson — was blacklisted from the Playboy Mansion. In the early 2000s, Luke Wilson was slammed with a 'Do Not Admit' or 'DNA' to the Playboy Mansion after he tried to use the fame of his brother to gain access to the party.

According to Luke Wilson, he tried getting into one of the Playboy parties, and when he was asked whom he was attending the party with, he mentioned his brother. Luke wasn't attending with his brother, though, and was actually trying to pass one of his friends off as Owen. Luke Wilson admitted in several interviews that his friend doesn't look anything like his brother.

After being slapped with his ban, Luke Wilson called a woman at the Playboy Mansion to apologize for his actions. He also admits that while on the phone apologizing, he began to cry just a little bit.

His ban lasted a year and a half.

6 Hef's Girlfriends Have A 9:00 PM Curfew


When you think of the Playboy Mansion, you may think of it as this glamorous palace of sex and partying. That's successful branding, really, because, in reality, living at the Playboy Mansion is one of the hardest things a lot of former Playmates have had to do. There are a number of rules, originally hidden from the public, that Hef's girlfriends have to follow.

To start, if one of Hef's girlfriends breaks any of the rules, they lose their allowance for the week. This punishment is typically used on little kids and not something you would expect from a household known for throwing wild parties.

The strictest rule of all, according to one of Hef's former girlfriends, Izabella St James, was that girls needed to be back at the mansion by 9:00 PM. I know homeschooled children with a later curfew than that. The only exception to this rule was if the girls were out at a Playboy function or were being shown off at the club by Hef, which typically happened every Wednesday and Friday.

5 There's a Zoo at the Playboy Mansion

There's nothing that the Playboy Mansion doesn't have. There are countless rooms to have group 'naps' in, more pools than you could possibly need, an arcade, and, most surprisingly, a zoo. In fact, The Playboy Mansion is one of few private residences in America that holds a zoo license. According to Hugh Hefner, one of the first things that he did when he bought the property in 1971 was to create a zoo on the property.

The zoo is run by the Mansion's Animals Department, a small team of people dedicated to making sure the animals remain happy. Some of the animals at the zoo are peacocks, cockatoos, squirrel monkeys, flamingos, and African cranes. A number of the animals at the Playboy zoo were donated by people who bought exotic pets and could no longer take care of them.

As you'd expect, there are a number of bunnies at the zoo.

4 Underage Girls Partied At The Playboy Mansion


According to former Playboy Mansion resident Jennifer Saginor, it was fairly common to find underage girls on the property. Saginor said that normal rules don't apply to the Playboy Mansion — which becomes evident when you hear some of Saginor's childhood stories.

Growing up, Saginor lived at the Mansion with her father, who supplied drugs to Hugh Hefner and his friends. She had a very unusual childhood washing down Xanax, Quaaludes, and other prescription medication with alcohol when she was 14 years old. As a teenager, she experienced Playboy parties that some of us can only dream about. However, Saginor wasn't the only minor to attend the parties.

As you may be aware, a number of sexual assault accusations surfaced about Bill Cosby in 2014. One of these accusations was made by Judy Huth, who met Cosby on a film set in 1974 when she was 15 years old. Cosby invited Huth to a tennis club and later to a party at Hefner's home, where he put his hand down her pants and tried to make her perform a non-consensual sexual act.

3 Drugs Were In Abundance At The Mansion

Jennifer Saginor was the daughter of "Dr. Feelgood," a man who lived at the Mansion and supplied Quaaludes, pain meds, stimulants, antidepressants, and Viagra to Hugh Hefner and a number of his bunnies and house guests. Amphetamines were regularly given to Playboy bunnies to help them diet and maintain a weight that Hefner believed to be ideal.

When it came to partying at the Playboy Mansion, marijuana was smoked in abundance. The harder drugs, like cocaine, weren't allowed to be taken in public. Hollywood hot shots seeking highs needed to find a private area to snort a few nose beers before returning back to the party.

It wasn't a matter of Hefner disapproving of drugs — it was a matter of maintaining an image. You're going to attract a lot of unwanted attention from authorities if people are snorting lines of cocaine off of your kitchen table with hundreds of people around.

Today, drug use at the mansion has seemingly slowed down. Parties are fewer, and the bunnies aren't force-fed amphetamines (or so we're led to believe).

2 Hef's Girlfriends Would Pretend To Have Sex With Each Other


Holly Madison is one of Hugh Hefner's former girlfriends, and star of the reality show Girls Next Door. In 2015, Madison released her memoir Down The Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, which debuted at #1 on the New York Times Bestseller list. She tried to earn an invitation into the Playboy Mansion when she was 21 while working at Hooters. Eventually, she caught Hefner's attention, and he invited her within weeks to live at the mansion. She went on to date Hefner for 7 years.

When she moved in, Hefner was around 75 years of age. As such, she thought there wouldn't be much to do in terms of making sure his sexual needs were met. The other girlfriends in the mansion assured her that she didn't have to actually have sex with Hefner because of a trick that some of them knew.

Hefner enjoyed watching his girlfriends enjoy each other's company in the bedroom — even if they weren't bisexual — and would generally take care of himself. When he did want to have s*x, his girlfriend's would often encourage him to sleep with his newest girlfriend.

To avoid sleeping with him, the girls would pretend to make out with each other. The room was dark enough that Hefner couldn't really see what they were doing, so many of them pretended to be having a lot more fun than they actually were. Madison recalls her first night in Hefner's bedroom where a fellow girlfriend whispered in her ear to "fake the f*ck."

1 Hefner Loves Using Quaaludes

Hugh Hefner is a massive fan of Quaaludes, according to a former girlfriend. The drug, methaqualone, is a sedative that was given to patients as a treatment for insomnia in 1970. Patients quickly discovered that if you stayed awake, you would feel a high like no other. The drug became popular among hippies and high rollers chasing the latest craze and was quickly made illegal by authorities around the world.

In Holly Madison's memoir, Down The Rabbit Hole, the former Playboy bunny revealed that Hefner had offered her Quaaludes the first time that they went out clubbing together. Hefner said that in the '70s, Quaaludes were referred to as "thigh openers." If that's not the creepiest thing an old man could say to a young lady trying to establish herself as a model, I don't know what is.

However, Kendra Wilkinson, who appeared alongside Holly Madison in the reality series Girls Next Door, denied Maddison's Quaalude accusations. As part of an interview on the radio show Man Cow, Kendra Wilkinson said, "Hef has f*cked thousands of women; he doesn't need no Quaalude, b*tch. Hef got p**sy without drugs, people! Come on!"

Sources: radaronline, wikipedia,, lifeandstylemag, 

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