For the longest time, the Playboy Mansion has been the sight of crazy, star-studded parties and scantily dressed women. However, this does not mean that the iconic building has changed much through the years. Without a doubt, the walls of this place have seen many interesting things play out. Hugh Hefner resided and hosted people in this huge Los Angeles mansion from 1974 until the time of his death. The estate cost him $1.1 million, but we are sure that this has since changed. How much exactly has it changed since then? We are here to find out! You probably did not know that this was not his first Playboy mansion either…
Hugh Hefner And Carrie Leigh
You are looking at a photo taken at a party in the mansion in 1986. This shows Hugh Hefner posing with Carrie Leigh, who is on the right. She had been an actress at the time. On top of that, she was no more than 19 years old when she first met the magazine magnet.
Hugh Hefner And Carrie Leigh
Victoria Silvstedt Is The 1997 Playmate Of The Year
In December 1996, Victoria Silvstedt had the opportunity to appear on the cover of the Playboy magazine. Readers of the publication soon became familiar with her after that. Here she is posing with a copy of the magazine after she was awarded the Playmate of the Year title all the way back in 1997.
Victoria Silvstedt Is The 1997 Playmate Of The Year
The Playmate Of The Year
If you have the right personality and the right look, it was possible to make a full-time career out of modeling for Playboy. Every year, a centerfold is given to the Playmate of the Year. This model also got $100,000 and a car. That does not sound bad to us at all. Check out Heather Kozar, who was the Playmate of the Year in 1999.
The Playmate Of The Year
Back In The Day
While you had to put on bunny ears to walk through its doors, the Playboy mansion was not exclusive to celebrities. As a matter of fact, it was not even exclusive to adults. A Redditor called Hoop_day shared an old photo of his grandpa with a few bunnies at the mansion. The best (or worst) part of the story was that he was only 16 years old when this photo was snapped.
Back In The Day
Eugena Washington Is The 2016 Playmate Of The Year
In 2016, Eugena Washington was awarded the title of the Playmate of the Year. The model actually made history in more ways than one. She was the first titleholder after the magazine decided to put an end to its nude centerfolds. Aside from that, she was also the last PMOY to be announced by Hugh Hefner himself. He died the year after that, but this photo shows the pair posing for the cameras.
Eugena Washington Is The 2016 Playmate Of The Year
The Original Playboy Mansion
Did you know that the Chicago mansion came before the Hollywood Playboy mansion? Indeed, it did not become iconic, but it was once another hedonistic and happening place during its heyday. This photo shows a group of people having a blast at one of Hugh Hefner’s parties. It was taken in 1961.
The Original Playboy Mansion
Welcome To The Grotto
Most of the fun at the Playboy mansion takes place at the grotto. This is a famous rock-covered pool that has hosted a lot of famous people. Important moments have taken place here as well. Below, you can see two unidentified women positing in the Grotto during a party in 2008.
Welcome To The Grotto
You Could Rent It For Private Events
You might not have known that you could rent the Playboy mansion for private events. Of course, it would have cost you a lot of money. Can you believe that this was taken at a bar mitzvah in the ‘90s? We wonder who came up with the idea to hold such an event at a place like this one. We are just glad that he looked genuinely happy.
You Could Rent It For Private Events
They Held Charity Events Too
There is no way we can deny that there was a lot of partying at the Playboy mansion in the past. This does not tell the whole story, however. Celebrities sometimes stopped by for a different and less hedonistic reason. Check out Farrah Fawcett at a charity tennis competition back in 1976.
They Held Charity Events Too
Not Someone You Expected
If Roseanne Barr can pull off a bunny outfit, you can probably do it as too. We will never cease to be astounded by all the things that have happened at the Playboy mansion. Here is a photo of the actress at “The Hoppening,” which was an AIDS benefit that Hugh Hefner hosted in 1994.
Not Someone You Expected
Brande Roderick Is The 2001 Playmate Of The Year
Aside from all the beautiful women, you will see many beautiful cars at the Playboy mansion as well. Hugh Hefner was a fan of the finer things in life, after all. Brande Roderick was snapped as she posed in front of the Boxter Porsche she received as the Playmate of the Year. Aren’t you jealous of this beauty?
Brande Roderick Is The 2001 Playmate Of The Year
Its Fiftieth Anniversary
In 2003, Playboy magazine celebrated its 50th anniversary. Hugh Hefner wanted to commemorate it unforgettably. You probably want to know what was going on when this photo was snapped. Below, you can see Hefner posing with models who were in the running to be the Playmate of the Year.
Its Fiftieth Anniversary
A Beatle Among The Bunnies
Whoa, will you look at this photo of Harry Nilsson, Ringo Starr, and an unidentified third person? They had been enjoying a drink at the Playboy mansion in 1975. You probably know Starr as the drummer of the Beatles. The Fab Four split up five years before the party in question. On the other hand, Nilsson has been called “the American Beatle.” We are not surprised to see that the two of them know each other!
A Beatle Among The Bunnies
It Is A Family Matter
Well, we can see why people assume that Hugh Hefner is not a family man. This photo might prove you wrong. Here he is with Christine, his daughter, at the Playmate of the Year luncheon in 1982. He had four kids. Christie even served as the CEO of the magazine until 2009. Cooper, her half-brother, also took on the position until he left to join the Air Force in 2019.
It Is A Family Matter
Making A Guest Appearance
Over the years, Hugh Hefner has entertained the rich and the famous in his Playboy mansion. In the ‘90s, however, the tables turned. The magazine magnate himself became a guest on the fourth season of The Fresh Prince of Bel-Air. In the episode in question, Carlton and Will tag along with Hilary in a quest to meet Hefner while she poses for Playboy magazine.
Making A Guest Appearance
The Most Infamous Guest
Hugh Hefner has found himself in the company of many stars and celebrities over the course of his life. However, some guests wound up being less beloved later on… A good example would be O.J. Simpson. The infamous athlete paid the Playboy mansion a visit in 1979. We are sure that, at the time, no one knew what was going to happen to him in the next three decades…
The Most Infamous Guest
Leif Garrett And His Sister
Here is Leif Garrett with his sister at a Playboy mansion party back in the ‘70s. We have no idea why he would choose to dance with his own sister in a place full of lovely ladies. However, the truth is that this is far from the worst decision that the singer was going to make in life.
Leif Garrett And His Sister
More To It Than Partying
Is there any reason to go to the Playboy mansion if you are not looking to party? The answer is yes! The truth is that the place is not just for people into sex and booze. This photo might be enough to convince you that this is the case. Here is a gaming room that came with two Playboy-themed pinball tables.
More To It Than Partying
It Is Always One Big Party
You never know who you are going to meet when you head to the Playboy mansion. It is a given that there will be tons of models and celebs around, but it is impossible to guess which ones. In 1999, actor Vern Troyer was around one night. He was blowing up at the time because of Austin Powers. The Bernaolo twins, who are considered Playmate royalty, were also around.
It Is Always One Big Party
Pamela Anderson And Bret Michaels
You can see Pamela Anderson and Bret Michaels posing at a charity gala at the Playboy mansion in the photo below. She was a regular sight at both the mansion and the magazine itself. The star has graced the pages of many issues. In 2015, she became the last model to pose nude in its centerfold too!
Pamela Anderson And Bret Michaels
Some Parties Feel More Like Chores
Even though a press party is not the most fun event, it is inevitable if you are a celebrity. If you have absolutely got to do it, the least you can do is be dressed to the nines at the Playboy mansion! This is a photo from a press party attended by the likes of Corey Feldman and Shannon Malone in 2000.
Some Parties Feel More Like Chores
The Original Mansion In Chicago
We all know about the Hollywood location, but the Playboy mansion was once based in Chicago. Hugh Hefner bought it in 1959. After he purchased the second one, he still divided his time between both places in the ‘70s. The original mansion did not have as much glitz and glamor as the one in California, but it had many amenities and space. In 1993, it was sold and then transformed into condos.
The Original Mansion In Chicago
The Mansion At The Moment
Whoa, will you look at this aerial view of the Playboy mansion? This was taken in 2005. We knew that it was big, but it is amazing to see just how huge it really is. Aside from all the bars and pool, it is also home to a basketball court, a pipe organ, and a zoo. It needed 80 staff employees to keep it running!
The Mansion At The Moment
If You Wanted To Promote Your Project
A lot of concerts have also been held at the Playboy mansion in the past. It was the best venue if you wanted to promote a big project. Look at this photo if you want an example. We have Sean Combs, also known as P. Diddy, to promote Hot Tub Time Machine in 2010. Even though the movie is not the best thing we have ever seen, we would love to have been at this party!
If You Wanted To Promote Your Project
Giving The Guests A Great Experience
It was not enough for Hugh Hefner to throw big parties there either. He wanted to give all of his guests an experience. He made sure to put in a lot of thought and effort into the décor and themes of each party. Taken in 2015, this photo shows the property being decorated for its yearly Halloween party.
Giving The Guests A Great Experience
Just Another Wild Night At The Playboy Mansion
As you can imagine, things can get out of hand at the Playboy mansion. However, it might not be exactly as you had in mind. This is not a place that brings images of peace, after all. The photo below was shot at a party in the Chicago mansion. An unknown guest was either heading in or out of the pool.
Just Another Wild Night At The Playboy Mansion
Two Lovely Ladies Draped In Fur
Up next, we have another photo taken at the original Playboy mansion in Chicago. It looks like it was a wild night! The hair was already enough indication as it is. This photo was shot in 1961. Two unidentified guests had been all cuddled up in fur! It sure looks cozy to us.
Two Lovely Ladies Draped In Fur
Shannon Tweed Is The 1982 Playmate Of The Year
This Canadian actress entered a high-profile relationship with Hugh Hefner in the ‘80s. We are sure that it is not all that easy to be linked to someone so famous. You can see Shannon Tweed below as she poses inside the Playboy mansion. She also earned the Playmate of the Year title in 1982.
Shannon Tweed Is The 1982 Playmate Of The Year
Robin Williams And Whoopie Goldberg
We doubt that we would have heard much about the Playboy mansion if it were not for its huge, lavish gatherings. Mind you. The parties were occasionally organized for a good cause. In 1994, Robin Williams and Whoopie Goldberg were both spotted at the Children of the Night fundraiser at the mansion.
Robin Williams And Whoopie Goldberg
Julie Cialini Is The 1995 Playmate Of The Year
Every year, we find out which model earned the Playmate of the Year title. It was once a big event at the Playboy mansion. As expected, it got a lot of press coverage and featured a huge celebration. In 1995, a model named Julie Cialini received this honor. Here she is with a blowup of her Playboy cover!
Julie Cialini Is The 1995 Playmate Of The Year
A Race To The Playboy Mansion
It was always interesting to see which celebrities were attending the parties at the Playboy mansion. There was no way to foretell who you were going to run into at these events. You just had to be there. This is a photo of racer Bruno Junqueira in front of his vehicle. He was accompanied by a couple of Playboy bunnies in this shot!
A Race To The Playboy Mansion
There Were A Lot Of Hollywood Events
The Playboy mansion became a common venue for Hollywood premieres and events. Taken in 2017, this photo shows two playmates at a launch party for Amazon. Can you guess what all the hullabaloo was about? You were right if you guessed that guests had been celebrating a new American original series show called American Playboy: The Hugh Hefner Series.
There Were A Lot Of Hollywood Events
Paris Hilton And A Parrot
Here is a photo showing Paris Hilton being upstaged by someone else. We are sure that this is not something that happens all that often! To be specific, she was outdone by a white parrot. She had been at the mansion that night to attend a wildlife fundraising event called “Parrots in Paradise.”
Paris Hilton And A Parrot
Ryan Seacrest And Hugh Hefner
You probably know Ryan Seacrest for hosting American Idol and other similar TV shows. If you ask us, he has never been more fabulous than when he announced the 2003 Playmate of the Year. This photo shows the host and Hugh Hefner at the Playboy mansion before the big reveal.
Ryan Seacrest And Hugh Hefner
Dita Von Teese
Did you really go to a Playboy mansion party if a woman did not remove her clothes at one point or another? In 2003, Dita von Teese was willing to oblige. The burlesque icon performed for Hefner and all the guests in attendance. This happened at a launch party for what used to be known as Spike TV. It has since rebranded into Paramount Network!
Dita Von Teese
It Is First And Foremost A Family Business
Perhaps you think that it is strange for something like Playboy magazine to be a family business. You are not the only one. No matter what we think, a couple of the Hefner kids decided to help run the company in their own way. Here is Cooper Hefner posing with Dani Mathers. The model received the honor of becoming the Playmate of the Year in 2015!
It Is First And Foremost A Family Business
Welcome To The Playboy Mansion
It is hard to deny that Playboy likes spectacle. We doubt that it came as a surprise that Hugh Hefner wanted to enchant his guests as soon as they walked into his mansion. In this photo, you can see what guests saw as they entered the lobby! This could be a regular entryway if you got rid of the oil painting of the pornographer in the back.
Welcome To The Playboy Mansion
Diana Ross With A Chimpanzee
Where else can you rub elbows with both a wild animal and some of the biggest musicians in history? The answer to that is none other than the Playboy mansion. Check out Diana Ross and a chimpanzee. This amazing photo was snapped during the annual Safari Brunch of the mansion in 2004.
Diana Ross With A Chimpanzee
Snoop Dogg With The Bunnies
Even though the Playboy mansion served as the private residence of Hugh Hefner, no one will say that Snoop Dogg seems out of place here. In fact, he looks right at home in it in this snapshot. We love this photo of the rapper with a couple of Playboy bunnies. It was taken at a party at the mansion sponsored by Colt 45 and the musician himself!
Snoop Dogg With The Bunnies
It Truly Marked The End Of An Era
Hugh Hefner passed away from a sepsis infection on September 27, 2017. Even though some folks wrote him off as nothing more than a pervert selling scandalous magazines, it is important to note that he left an impact on both politics and the publishing industry. Take a look at this photo of a makeshift memorial created by fans. They left it outside the Playboy mansion in California a day after his untimely passing.
It Truly Marked The End Of An Era