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40 Pictures That Show How the Playboy Mansion Has Changed Over the Years

Every Night is a Party

This photo was taken at a 1986 party in the Los Angeles Playboy mansion. In it, Hugh Hefner poses with Carrie Leigh (on the right). 

Leigh was an actress who was only 19 when she met Hefner in Canada. 

( Photo by Paul Harris/Getty Images )
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Victoria Silvstedt

Victoria Silvstedt became a staple of the Playboy company after appearing on the cover of their December 1996 issue. 

In this photo, Silvstedt poses with a copy of Playboy magazine after winning the title of Playmate of the Year in 1997. 

(Photo by Frank Trapper/Corbis via Getty Images)
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Playboy MVP

If you had the right look at the right personality, you could almost make posing for Playboy your full-time career. Each year, a centerfold is chosen as "Playmate of the Year" and given $100k and car--not a terrible paycheck for getting naked. 

In this photo, Heather Kozar poses for her 1999 Playmate of the Year photoshoot. 

(Photo by David McNew)
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Those Were the Days

You might have to throw on a pair of bunny ears to get in, but the Playboy mansion has never been a place completely exclusive to the rich and famous. Or even exclusive to legal adults! 

Reddit user u/Hoop_dav shared this old photo of his grandfather posing with some bunnies at the mansion. The real kicker? He was just 16 when the photo was taken! 

(Image via Reddit)
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Making History

When Eugena Washington was chosen as Playboy's 2016 Playmate of the Year, she made history in two ways. She was the first PMOY after the magazine's controversial decision to end their nude ceterfolds, and she was the last winner to be announced by Hefner before his death in 2017. 

In this photo, Hefner and Washington pose for the cameras at the conference announcing her win. 

(Photo by Charley Gallay/Getty Images for Playboy)
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Chicago Style

Before there was the Hollywood Playboy mansion, there was the Chicago mansion. While it may not have the same iconic status, it was still a very hedonistic, happening place to be during its day. 

In this photo, we see a group of people enjoying themselves at a party hosted by Hefner in 1961. 

(Photo by Slim Aarons/Getty Images)
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The Grotto

The grotto is the part of the Playboy mansion where all the most fun takes place. The famous rock-covered pool has been host to many famous people and important moments. 

In this photo, two unknown women pose in the Grotto at a 2008 party. 

(Photo by John Shearer/WireImage)
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You're a Man Now

If you had the money, the Playboy mansion was available for private events--no matter how misguided they might have been. 

In this photo, we see a shot from a 1990s bar mitzvah. It takes some real chutzpah to have a religious party surrounded by women in bunny ears. 

(Image via Reddit)
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For Charity

Sure, there was plenty of partying going on at the Playboy mansion back in the day, but that wasn't the whole story. Celebrities would sometimes stop by for a higher cause, too. 

This photo features actress Farrah Fawcett as she poses during a charity tennis tournament in 1976. 

(Photo by Fotos International/Frank Edwards/Getty Images)
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An Unexpected Guest

If Roseanne can look good in a bunny outfit, then literally anyone can. It will never cease to amaze you what you find at the Playboy mansion. 

This photo of Barr was taken in 1994 at "The Hoppening"--an AIDS benefit hosted by Hefner. 

(Photo by Ron Davis/Getty Images)
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Brande Roderick

At the Playboy mansion, you're just as likely to spot a beautiful car as you are a beautiful woman. Hefner loved the finer things in life, automobiles included. 

Here, Playmate of the Year Brande Roderick poses in front of her new Boxter Porsche. In addition to a cash prize, every year's winner also recieves a fancy car. 

(Photo by Frank Trapper/Corbis via Getty Images)
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Playboy History

2003 marked the 50th anniversary of Playboy magazine, and Hefner wanted to make the anniversary year one that readers would never forget. 

In this photo, Hefner poses with some aspiring models who hope to be chosen as the magazine's 50th anniversary Playmate. 

(Photo by David Klein/Getty Images)
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Beatles & Bunnies

In this photo, Ringo Starr, Harry Nilsson, and an unknown third party have a drink at a party in 1975. 

Starr is most famous as the drummer for the Beatles (although they had broken up 5 years earlier when this photo was taken). And Nilsson was a musician in his own right, was sometimes known as "the American Beatle," so it's no surprise to see him rubbing elbows with Starr. 

(Image via Reddit)
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All in the Family

You might not peg Hefner as a family man, but in this photo, we see him with his daughter, Christie, at the 1982 Playmate of the Year luncheon. 

Hefner actually had four children during his life. Christie (pictured) worked as the CEO of Playboy until 2009. Her half-brother, Cooper, also acted as CEO of the company until 2019 when he joined the Air Force. 

(Photo by Paul Harris/Getty Images)
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Worlds Collide

Hugh Hefner and the Playboy mansion played host to many famous guests, but in the 90s the tables turned--they were the guests on one of the hottest sitcoms of the time. 

In season 4 of The Fresh Prince of Bel-Air, Will and Carlton tag along to meet Hugh Hefner when Hilary goes to the mansion to pose for Playboy

(Image via Reddit)
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An Infamous Guest

Hefner hosted countless celebrities and stars during his life at the Playboy mansion. But not every famous person stayed as beloved as they were when they visited the mansion. 

Case in point: O.J. Simpson. Here we have a pic of the infamous athlete and actor as he visits the mansion in 1979. If only he knew what the next 30 years would bring for him...

(Photo by Frank Edwards/Fotos International/Getty Images)
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'70s Stars

In this photo, we've got Leif Garrett and his sister at one of the iconic Playboy mansion parties of the '70s. 

We're not sure why Garrett would be dancing with his sister (presumably) in a room full of beautiful women, but honestly, it's not the worst decision he would make in his life. 

(Photo by Brad Elterman/FilmMagic)
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It's Not All Partying

We're not sure why anyone would come to the Playboy mansion except to party, but if you find yourself in that situation, there's actually a lot on the property that doesn't have to do with sex or booze. 

In this photo, we see a shot of the gaming room in the mansion--including two Playboy themed pinball tables. 

(Photo by GABRIEL BOUYS/AFP via Getty Images)
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It's Always a Party

If you're visiting the Playboy mansion, you never know who you're gonna meet there. Sure, it will probably be celebrities and models--but which ones? 

If you happened to be there in 1999, you might run into actor Vern Troyer, who was in the middle of a celebrity blowup thanks to Austin Powers. Or you might see Playmate royalty, the Bernaola twins. 

(Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
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A Playboy Legend

In this photo, Pamela Anderson and then-boyfriend Bret Michaels pose at a charity gala hosted at the Playboy mansion. 

Anderson was a staple not only at the mansion, but also in Playboy magazine. She appeared in numerous issues, and, in 2015, was the last model to appear nude in the centerfold. 

(Photo by Ron Davis/Getty Images)
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Partying is a Job

Press is no fun, but it's inevitable for a celebrity. But if you've got to do it, why not do it in style at the Playboy mansion? 

In this photo from 2000, we see actors Shannon Malone and Corey Feldman during a press party at the mansion. 

(Photo by Jeff Kravitz/FilmMagic, Inc)
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The OG Mansion

Before the famous Hollywood location, there was the Playboy mansion in Chicago. Hefner bought the place in 1959, and, even after the purchase of the second mansion, still split his time between the two residences during the 70s. 

This orignal mansion didn't have quite as much of the glitz and glamor of the Hollywood mansion, but there was still plenty of space and amenities to throw some crazy parties. The propery was sold in 1993 and turned into condos. 

(Image via Reddit)
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The Mansion Today

Here, we see an aerial view of the Playboy mansion taken in 2005. You expect it to be massive, but this is impressive even for the wildly rich. 

In addition to countless pools and bars, the mansion is also home to a zoo, a basketball court, and a pipe organ. The property allegedly requires a staff of 80 to maintain. 

(Photo by Shane Gritzinger/FilmMagic)
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Mansion Business

The Playboy mansion has been known as a hot spot for concerts throughout the years, as well as a place to promote your next big project. This photo manages to do both. 

In it, we see Sean "P. Diddy" Combs performing a 2010 concert at the mansion to promote the upcoming film Hot Tub Time Machine. The movie might have been meh, but this party was clearly popping. 

(Photo by Jeff Kravitz/FilmMagic)
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The Haunted (Playboy) Mansion

It wasn't enough for Hefner to just throw huge parties at the Playboy mansion--they had to be experiences. The themes and decor that went into creating a Playboy party were truly a sight to behold. 

In this photo from 2015, we see the property getting decorated for the annual Halloween party, which I'm sure was some spooky fun. 

(Photo by Jonathan Leibson/Getty Images for Playboy)
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A Wild Night

Things can get pretty crazy at the Playboy mansion, as you might imagine--it's not like the place is known for family fun in peace and quiet. 

This photo was taken at a party in the original Playboy mansion in Chicago. In it, an unknown guest is either making a dash to or from the pool. 

(Photo by Slim Aarons/Getty Images)
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Venus in Furs

Here is a shot from yet another wild night at the original Chicago Playboy mansion. As if their hair wasn't enough indication, the photo was taken in 1961. 

In the photo, two unnamed guests at the mansion cuddle up in fur. 

(Photo by Slim Aarons/Getty Images)
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Shannon Tweed

Shannon Tweed is a Canadian actress who famously dated Hugh Hefner in the 1980s. 

In this photo, Tweed poses in the Playboy mansion after she was named Playmate of the Year in 1982. 

(Photo by Paul Harris/Getty Images)
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Seeing Stars

The Playboy mansion was famous for it's large, lavish gatherings--and these parties were sometimes actually for a good cause. 

In this 1994 photo, comedians Whoopi Goldberg and Robin Williams are in attendance at Playboy's Children of the Night charity fundraiser. 

(Photo by Joan Adlen/Getty Images)
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Julie Cialini

The annual crowning of a new Playmate of the Year was a big to-do at the Playboy mansion. It often featured a massive celebration and lots of press. 

In 1995, model Julie Cialini was chosen for the honor. In this photo, she poses with a blowup of her winning Playboy cover. 

(Photo by Frank Trapper/Corbis via Getty Images)
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Racing to the Mansion

The Playboy mansion brought rich and famous people from all walks of life. There was never any telling who you might see there. 

In this photo, racer Bruno Junqueira poses with some of the Playboy bunnies in front of his car. 

(Photo via Jamie Squire/ALLSPORT/Getty Images)
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Fiction or Real Life?

As time went on, the Playboy mansion became a hot spot for Hollywood business and premieres. In this photo, taken in 2017, two playmates pose at an Amazon launch party. 

That night, guests were celebrating the new Amazon original series American Playboy: The Hugh Hefner Series

(Photo by Charley Gallay/Getty Images for Amazon)
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The Playboy Jungle

This is one of the few photos where Paris Hilton is upstaged by her partner--and in this case, that happens to be a white parrot. 

That night, Hilton was visiting the mansion for a wildlife fundraiser called"Parrots in Paradise."

(Photo by Jean-Paul Aussenard/WireImage)
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Worlds Collide

Ryan Seacrest has had some pretty memorable gigs, but most probably weren't as fabulous as when he was chosen to announce the 2003 Playmate of the Year. 

In this photo, Seacrest and Hefner meet at the Playboy mansion before the big announcement is made. 

(Photo by David Klein/Getty Images)
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Don't Teese Me

It wouldn't be a Playboy mansion party without a woman removing her clothes. And in 2003, burlesque icon Dita Von Teese was more than happy to oblige. 

In this photo, Von Teese performs for Hefner and his guests at the launch party for Spike TV. 

(Photo by Robert Mora/Getty Images)
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Family Business

It might seem strange to think of Playboy as a family business, but several of Hefner's children have had a hand in running the company. 

Here, Hefner's son, Cooper, poses with Dani Mathers--who was chosen as the 2015 Playmate of the Year. 

(Photo by Jason Kempin/Getty Images for Playboy)
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Welcome to Playboy

Playboy is all about spectacle, so it's no surprise that Hefner wanted to dazzle guests from the moment they walked into the mansion. 

This photo show what guest see when they walk into the lobby of the mansion. If you ditched the oil painting of the famous pornographer in the back, this could look like anyone's entryway. 

(Photo via HECTOR MATA/AFP via Getty Images)
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Disco Animal

Only at the Playboy mansion can you brush elbows with one of the most famous musicians of all time AND maybe a wild animal or two!

In this photo, Diana Ross poses with a chimpazee while she attends the mansion's annual Safari Brunch in 2004. 

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Snooping Around

The Playboy mansion might have been Hugh Hefner's home, but I don't think anyone is gonna argue that Snoop Dogg looks out of place in this venue known for beautiful women and debauchery. 

In this photo, the rapper poses with some of the Playboy bunnies at a mansion party sponsored by Snoop Dogg and Colt 45--because of course. 

(Photo by James Lemke Jr/Getty Images)
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The End of an Era

Hugh Hefner died on September 27th, 2017 due to a sepsis infection. While some people just wrote him off as a pervert selling nudie mags, he made an impact in both the world of publishing and politics. 

This photo shows a makeshift memorial than fans created at the gates of the Playboy mansion a day after his death. 

(Photo by Allen Berezovsky/Getty Images)
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