Old Pictures Of The Playboy Mansion Captured By Rare Visitors

What Happens At The Mansion……

At some point, we've all wondered about what goes on in the exclusive playboy mansion. The first thing that comes to mind are the bunnies! But there's more to the mansion than we previously knew and it's time for all the secrets to be revealed! 

Imagine Hugh Hefner coming around the corner with gorgeous women surrounding him. His charming smile and self-assured nature make every guest feel at home and lose their inhibitions. The parties were legendary, and finally, we've got the photographic evidence to see exactly what the hype was about!  Here are the top moments captured by celebrity cameras ...

Where Did The Reputation Start?

The Playboy enterprise was not an overnight success. The company had an uphill battle convincing America that reading and talking about hedonistic activities were acceptable. Having launched in 1953, the company almost faced bankruptcy before being accepted by mainstream media.  

When they began to make a profit, rumors started about private parties being hosted by Hugh Hefner. At first, the parties were extremely exclusive and required an invitation. It wouldn’t be long before all celebrities were fighting to get in the front door! And here's what they got up to. 

Hugh Was A Fan Of Bringing His Work Home

A mogul like Hugh Hefner needed to be passionate about his work. It went without a question that the face of the Playboy empire would be their CEO. Hugh got married in 1949 to his high school sweetheart Mildred Williams. Was he able to handle the pressure of the spotlight and his personal life? 

The couple had two children but eventually divorced in 1959 due to the pressure of Hugh’s work-life balance. Hugh was about to embark on a whole new journey and needed to focus on the future and his empire. No one could have predicted who would walk through the mansion's doors next.

A Bachelor Pad For A Legend

The same year Hugh’s divorce was finalized, he signed the papers for the original playboy mansion. The first mansion was bought in Chicago's Gold Coast District and had 70 bedrooms over 30,000 square feet. The mansion would not reach Los Angeles until almost seventeen years later. 

It was time for Hefner to embrace the environment he was creating. What kind of guests would come to his new mansion and enjoy his decadent parties? After living in Chicago for so long, would the team be able to adjust to the warm climate of Los Angeles? Things are about to get steamy!

Actors And Athletes Partied Together

Hugh loved having the company and surrounding himself with the most up-and-coming actors and star-athletes. One day he introduced Arnold Schwarzenegger to Kareem Abdul Jabar and looked ecstatic. 

While the parties and celebrities were fun, guests wondered what else would be in store for Hugh's life outside of Playboy parties and his magazine empire? Would he peak too early before getting to enjoy a lavish lifestyle only a few of us can dream of?

When Did The Bathrobe Begin?

In 1971 when Hugh bought the first Chicago-based Playboy mansion, wearing the bathrobe felt dangerous. It felt risque! It quickly became his uniform when throwing parties and became synonymous with his playboy lifestyle.

The original Chicago mansion had many hidden rooms and spaces that played host to secret concerts. Hugh was an avid music collector and loved to have up-and-coming artists perform for him and his favorite Playboy models. Can you imagine attending one of these private performances? Well, you can now! 

Music Library And Performances

Hugh had a large collection of music and loved to share his taste with friends. In the beginning, he would be in charge of selecting what would be played but eventually brought in musicians to perform. A few famous names that performed include Fleetwood Mac and Bob Dylan. 

In more recent years, the Playboy mansion became a popular location for music videos. The most recognizable scenes include the music video for ‘Beverly Hills’ by Weezer and duet ‘Work-It’ by Nelly & Justin Timberlake. How many full-time staff members do you think it took to get these parties organized and successful? 

The Magic Behind The Scenes

The mansion sprawls across 5.3 acres and has 29 rooms. It includes a grotto, tennis courts, a screening room, dining rooms, and many bedrooms. It would take a small army to make sure everything was kept up to a pristine condition that guests and Hefner expected. 

The mansion was always buzzing with people between maids, butlers, chefs, security, and lawn maintenance. Did all the guests appreciate the hard work at each party, or were celebrities taking these moments for granted? Well, let find out now with these rare pictures ...

Rare Moments Captured By Guests

Celebrities never took a moment for granted inside the mansion’s iconic parties. It always felt like a dream and honor to walk through the front doors or finally have your picture taken with a famous bunny! Over the years, there have been various events, from themed parties to birthdays, all taking place in these hallowed halls. 

The mansion was also used as a filming location, and this was how some guests got to see inside the magical mansion. One show, in particular, had a very famous lead actor who could not believe his luck to be invited back to the mansion. 

The Fresh Prince Got An Invite

In 1994, Hugh Hefner had a guest appearance on the show ‘Fresh Prince Of Bel Air.’ After he did his episode, he extended an invitation to the cast to come and visit him. They all looked pretty happy for the invite and to go to the mansion. 

The fresh prince cast was television royalty, so it’s easy to understand how they managed to secure an invite. Did Hugh ever invite people he was unsure of? Well, there is this one rapper with controversial lyrics who made an appearance at the mansion. 

The Real Slim

When Marshall Mathers was being introduced to the world as Eminem, he managed to secure an invite to a famous playboy mansion party. The young rapper stayed on his best behavior while at the party but years later acted badly towards one of Hef’s girlfriends. In 2006 he allegedly threw water over Kendra Wilkinson while filming a rap video. 

The pair says it was all done in jest, but Hef is one to hold a grudge, and the rapper wasn’t invited to any parties after. This next musician met someone at a Playboy mansion party that would change the rest of his life. They say love finds you in the most unexpected places, and the Playboy mansion would definitely be unexpected!

A Kiss For Bunnies

Rock legend Gene Simmons went to a Playboy mansion party in 1983 and left with something better than just memories. Simmons met his wife, former Playboy model Shannon Tweed at a party in 1983, and the couple bought their own mansion in 1984.

This next musician appeared at the mansion several times after his first visit. Did touring this mansion ruin his squeaky clean image, or did it stay a secret for years to come? Find out who this mystery musician is at the Playboy mansion parties.

Justin Timberlake

This famous musician went to the Playboy mansion when he was part of his group NSync and also as a solo artist. He also got the amazing opportunity to film a music video at the mansion with fellow artist Nelly. The pair collaborated for the song ‘Work It.’

When NSync took a hiatus in 2002, the lyrics of one of their songs said, “You got to be seen at every party At the playboy mansion But, sad I know I gotta draw the line,” which made fans speculate if something had happened with one of the famous boy-band stars at the mansion. The next celebrity that rolled up to the mansion was also a sexual revolutionary icon, but would she be welcomed at the mansion?


Madonna was actually a long-time friend of Hugh’s because she had been on the cover of Playboy five times! The queen of pop is secure in promoting her body image and loved having the opportunity to capture her body in her youth. 

She would make appearances through the years when she was promoting new music and later in her career when she started doing films. Can you imagine moving next door to the Playboy mansion? Would you sneak into the parties or still hope for an invitation?

A Good Neighbour 

The famous couple Sonny & Cher lived next door to the Playboy mansion in their home, The Owlwood Estate. The famous singer also once appeared at the Playboy resort in Lake Geneva. When Cher went to the club, she made sure to dress the part, and we can only imagine how excited fans were of the unexpected performance.

At one point, Hugh began hosting a show called “Playboy After Dark” which featured performances from singers including James Brown and Fleetwood Mac. Who else has performed at the famous mansion? This next guest seems to blend in no matter where he goes. 

Snoop D-O-G-G

We aren’t surprised that this famous rapper had center stage when he performed at the mansion in 2009. Apparently, he arrived in style wearing a signature blue bathrobe and quickly became popular with the bunnies. 

This next guest was the opposite of Snoop but appreciated a good party just as much as the next person. We can’t help but wonder if guests were a little put off by his appearance or if they were fans and were equally excited to be close to him.

Marilyn Manson

In 2004 Marilyn Manson attended a famous Playboy mansion party and didn’t hold back from his standard appearance. The mansion is known for a light and fun dress code, meaning Manson’s signature pale skin and color contact lenses made him stand out even more. 

A couple of the Playboy bunny models were big fans of his work and were equally as excited to meet the famous musician. You never know who you’ll see or find when you get invited to a famous party, but did you also know there would be animals in attendance? Find out who was crawling around on all fours at the mansion besides the party animals.

 A Zoo License

Calling the mansion a paradise for party animals means more than you think! We didn’t realize you needed this to throw legendary parties, but the mansion actually has 150 animals on-site and has been classified with a zoo license for zoning. Different species include spider monkeys, cockatoos, African cranes, and peacocks.

The zoo is somewhere guests like to walk around, but it’s mostly closed after dark for everyone's safety. One location in the mansion gets more popular as soon as the sun goes down. Would you dip a toe into the warm mansion waters or swim in the other direction?

The Infamous Grotto 

While the mansion had a pool, it was more well-known for the private grotto. Guests could swim underwater and emerge in the secret lair for a completely different kind of party. With so many indiscretions, how was the Grotto maintained to keep its sanitation standard? 

Apparently, in 2011, the staff dropped the ball, and over 100 guests contracted Legionnaires disease. This is specifically transmitted through bacteria in water. It is easy to cure but has pneumonia-like symptoms. The same year this grotto broke out, a superhero walked through the mansion’s front door. Would he be welcomed with open arms?

Captain America Is A Patriotic Playboy

It was his patriotic duty to visit the mansion and make sure everyone was enjoying their time. In 2011, Chris Evans walked through the Playboy mansion doors and wasn’t rushing to leave. It was the year Captain America came out in theatres, and his life was about to change. With newfound celebrity status, Evans felt right at home and partied away until the early hours of the morning.

This next candid photo shows Hugh Hefner with one of his longtime friends. Unfortunately for this actor, his life fell apart due to legal proceedings in 2018. This friendship was meant to last as long as the Playboy reputation, but it just wasn’t in the cards.

Bill Cosby 

When Cosby first entered the comedy world, it seemed like he had a bright future. He became everyone’s favorite television dad on the ‘Cosby Show’ and enjoyed various levels of success throughout his career. In 2018 he was found guilty in multiple lawsuits and has disappeared from the public eye. 

Hugh Hefner had been friends with the comedian for years, and Cosby was a regular guest at the mansion parties. Unfortunately, his lawsuits dragged the Playboy mogul down with him, and Hugh was forced to testify against him. Hugh came to the defense of this next guest and made sure she got exactly what she wanted. 

Dita Von Tess

This burlesque star definitely doesn’t mind showing a little skin, but it needs to go by her rules. Hugh Hefner met the performer in the '90s and loved all of her artistic work. He immediately wanted her to perform at the mansion and promised her a Playboy cover. 

When it came time to discuss covers with the magazine team, Dita was disappointed that they weren’t going to give her the December issue. She decided to hold her own and refused to do a cover until Hugh had to be involved. Eventually, the star landed exactly where she wanted, but did Hugh Heffner’s life turn out the way he expected? 

The Stroke Of Luck

After a few years of partying hard, Hugh suffered from a minor stroke in 1985. It was a moment for him that made him realize life was short and he needed to focus on the things that mattered. Hugh wanted to try marriage again and decided to tie the knot with Kimberly Conrad in 1986. 

The couple had two children together, and Conrad was named Playmate of the year in 1989. Unfortunately, they separated in 1999 but didn’t formally divorce until 2010. Conrad and her children lived close by during the separation, and the family still had dinner together once a week. What would it be like to grow up in the Playboy mansion?

The Children of Bunnies

Hugh Hefner had four children in his life, starting with daughter Christie in 1952. From his first marriage with Mildred Williams, he also had a son named David. The siblings are opposites as Christie has chosen to get involved in the Playboy empire, and David leads a quiet life. 

His younger two children Cooper and Marston, were born and lived in the Playboy mansion for almost ten years. Similar to their older siblings, one chose to help run the Playboy empire, and the other went into the world of art. What does it look like to work next to your dad at Playboy empire? 

Helping Daddy Run An Empire

Two out of Hefner’s four children are involved in the Playboy enterprise. His only daughter Christie worked for the company for 30 years and at one point held the title of CEO. Christy left her corporate role to focus on more charitable foundations and established the Hugh M. First Amendment Award. 

Cooper has been in his big sister’s shadow growing up and is recognized as Playboy’s Chief Creative Officer. He has also taken an interest in tech startups and was a CEO for the media brand HOP. With two of his children running the business, what would an undercover journalist find out about Playboy?

Undercover Bunny Report

A household name associated with feminism, Gloria Steinman went undercover at a Playboy club for a month as one of her first journalism assignments. The report was published and detailed the wages girls would lose for different infractions and also what was really happening with clients. 

The report made Hugh Hefner adjust some rules with his employees and had a positive influence on the company overall. Hugh has been said to take equality seriously and didn’t want any of his employees to feel uncomfortable. A tale has been told about one famous guest, but do you believe the same sheets would still be found in the mansion today?

The King Had A Private Bedroom 

At some point in 1970, Elvis Presley was rumored to stay for one night in the Playboy mansion. Hugh is always eager to please his friends, and the king had the company of 8 playmates during his stay. The room has been kept in the same condition as the last time it was used. 

The King of music was a fan of Hugh’s lifestyle and a Playboy bunny favorite, but who were the people that Hugh loved more than anyone? Did he ever regret any of his romances? Find out about the one Playboy bunny that got away!

The One That Got Away 

When Hugh Hefner first got divorced, he had a slew of relationships with different Playboy models. One, in particular, made a big impact. Barbi Benton first connected with Hugh Hefner in 1969, but their romance quickly fizzled out. Almost a decade later, they started dating again in 1976. 

The pair didn’t stay together for too long, but Hugh always said he would love her forever. Later in life, he said in an interview not marrying her was one of his biggest regrets. It was hard to tell if the millionaire was ever heartbroken. He was rarely alone and also threw lavish theme parties. Do you know which famous quarterback attended the mansion’s biggest event in 2015? 

Touch Down On Fight Night 

In 2015 Peyton Manning played for the Denver Broncos and became the oldest quarterback to win a Superbowl. He was a guest at the Playboy mansion’s fight night-themed party and snapped this memorable picture with Hugh!  

Guests loved to mingle and got star-struck on the grounds often. You never knew who would cross your path. Can you believe there’s picture proof of this United States President attending a famous Playboy plush event? 

Before He Was President

Can you believe before he was elected into public office, this next guest made a public appearance at the mansion? He looks right at home, and we can imagine he was there more than once. Donald Trump, who always already had a playboy reputation, was right at home when he visited the mansion with his wife, Melania. 

It wasn’t easy to hold Hugh Hefner’s attention. Competition to win his heart was steep, but what do you know about the woman he dated for seven years and never married? Hugh will always say having several girlfriends is easier than one wife, but she was definitely running the show behind the scenes!

Who Is Holly Madison?

Holly Madison first got on the Playboy radar in 2001. She was a young model when she was invited to start living at the mansion full time. Eventually, she became Hugh’s number 1 girlfriend and had different privileges than other women in the mansion.

She dated Hefner for 7 years until he admitted he wasn’t going to marry her and didn’t want any more children. Holly left the relationship to marry and have two children with entertainment mogul Pasquale Rotella. She also published a tell-all book about her time living at the mansion. Would her experience be similar to Hefner’s third and final wife?

Hugh’s Third Wife Crystal Harris

Hefner met his third wife, Crystal Harris, when she was a psychology student and part-time model in San Diego. She attended a playboy mansion party with a friend, and her host quickly fell head over heels. The two were an official item by 2009 and then got married in a romantic New Years' Eve ceremony in 2012. 

In the last years of their marriage, Crystal struggled with medical complications from her surgical implants and was only just gaining her health back when her husband began to decline. She was devastated to lose him and no longer lives in the mansion. While everything seems like a party, is it possible for some people to go too far and get banned? 

Is It Possible To Get Banned?

The answer is yes! As gracious and giving as Hugh is to his celebrity friends, you can face being banned from the property and the premise if you step out of line. Famous celebrities who received a ban were NFL star Reggie Bush and actor Luke Wilson. 

Wilson was trying to sneak a friend into the mansion that wasn’t on the guest list. Apparently, Hugh takes this seriously, and Wilson was banned for a year due to his actions. When Wilson speaks about the experience in interviews, he says Hugh made the right call. What would the world be like after Hugh Hefner quit being a Playboy?

The End Of An Empire

On September 27, 2017, the world lost a visionary. Hugh Hefner made a large impact on the world of media and will be sorely missed. He is fondly remembered for his zest of life and adventurous spirit. It would make sense the very last party at the mansion would be in his honor. 

To celebrate his life, one last party was thrown after the famous host’s passing. What does this mean for the future of everyone that lives at the mansion? What are the future plans for this amazing architecture? This new owner has big plans up his sleeves! 

Who Owns The Mansion Now?

While everyone was wondering what would happen to the mansion, it turns out that Hugh had already made the arrangements in August 2016. The mansion was sold to Daren Metropoulos for a cool price tag of $100 million. One of the stipulations of the purchase was that Hugh Hefner would live in the mansion until the day he died. 

The new owner didn’t have a problem with that and already lives next door to the mansion! Metropoulos controls massive shares of popular food brands, including ‘Hostess’, and is estimated to have a net worth of $2.7 billion. He plans to restore the mansion to its original condition and keep it in loving memory to its famous previous owner.