The truth behind the Playboy Empire and Playboy Mansion heirs


While many of us have seen the effects of Playboy in the world, most of us have missed what life was like behind the doors of the mansion – unless you were one of the few that got an invite to the exclusive parties held within the walls. However, there were certain people that got an entirely new take on Playboy; Hugh Hefner’s children. Especially his two sons, Marston and Cooper, who got to live their lives within the Playboy Mansion. Okay, maybe our childhoods were pretty normal now we look back on it all. But was it really as strange as we think it was to grow up inside one of the most famous houses in the world? It’s time to find out.

The beginning of it all

Cooper Hefner was born on September 4, 1991, and is the youngest child of Hugh Hefner. You might think that growing up as the son of the Playboy Mansion millionaire would create quite the chaotic childhood? Well, maybe not. Sure, having a poster of your mom posing for the magazine hanging in the library might not be a usual feature in everyone’s house, but Cooper got to enjoy a games room and loving parents just like many others.

Picture of Marston Hefner in The Playboy Paper holding his younger brother, Cooper Hefner after he was born

Bunnies everywhere

Of course, being in the Playboy mansion didn’t mean Cooper was free from the life of the bunnies. However, life wasn’t always set to be this way. Hugh Hefner was once the 22-year-old geek that struggled to talk to girls. It wasn’t until 1953 when the first edition of the magazine was released that things began to take off. From there, it was weekly parties with the Playmates that introduced Cooper to the world he would one day grow up to inherit.

Black and white photo of Hugh Hefner surrounded by a group of Playboy bunnies smiling at the camera

Family time

Hugh’s time at the top of the Playboy empire did more than just fuel his bank balance; the millionaire was able to find love. After a divorce and a few failed relationships, Hugh met and fell for Kimberley Conrad in 1989. Kimberley was 26 years old when the pair tied the knot and had already been named as Playmate of the Year. She was well used to the mansion’s lifestyle, but now it seemed as though this star was ready for family life.

Photo of Hugh Hefner wearing a bow tie and suit with Playmate Kimberley Conrad wearing a black dress

Another brother

Hugh already had two children from his first marriage: Christie and David. However, two years after tying the knot with Kimberley, the couple welcomed another son, Marston, before youngest Cooper was born the following year. The two brothers might have been close in age, but it wasn’t long before their differences started to emerge. Cooper took a keen interest in his dad’s work life, while Marston was happier in his bedroom away from the action. This was only the beginning…

Black and white photo of a toddler reading an edition of Playboy magazine sat in a deckchair

Looks can be deceiving

Everything might have seemed peachy on the outside, but there was trouble brewing underneath for Hugh and Kimberley. The couple were married for ten years before they decided it was time to call it a day. Although they separated, the couple stayed married until 2009 for the sake of their two sons. Thankfully, the pair were able to keep things amicable, and Hugh was even spotted dating several other Playmates even though he was still married.

Hugh Hefner and Kimberley Conrad looking into each other’s eyes with Marston and Cooper on their laps

When two become one

Hugh and Kimberley were so determined to keep their children’s lives as normal as possible that they both took charge of parenting. So what better way to do that than by buying the mansion next door to the Playboy Mansion and knocking the two houses together? Now, both parents would always be there for their boys while being able to live their private lives. As if that wasn’t enough, Cooper and Marston could go between the houses as they pleased.

Kimberley Conrad and Hugh Hefner at a dinner event with one of their sons wearing a denim baseball cap

Motherly love

Growing up with two parents in two separate houses soon became the norm for Cooper and his brother. However, that didn’t mean they had to miss out on any part of their parents’ lives. In fact, Cooper admits Kimberley convinced Hugh to tone down his parties to more black-tie events so the boys could attend. Although Cooper has always been close to his mother, he admits his mom’s Playboy shots often made for some interesting topics of conversation as a child.

Hugh Hefner and Kimberley Conrad together at an event with their sons Marston and Conrad wearing waistcoats

Special parties

Although Kimberley managed to tame a lot of the weekly parties in the Playboy mansion, there were still certain times of the year where Hugh would go all out. Halloween and Christmas were special times for the Playmates as they all got into costumes and threw huge events. So what happened to the boys? Cooper admits when the parties were in full swing, “Security could go on babysitting watch to make sure my brother and I were kept in the house.”

Cooper Hefner with two Playboy bunnies dressed as Little Red Riding Hood and the Big, Bad wolf

Security turned babysitters

In fact, Hugh would enlist the help of his security staff to ensure Cooper and Marston were kept away from the parties. Cooper admits that he and his brother used to try and sneak in, especially when they were teenagers, but there was always a security guard there to stop them. Although he has never admitted what he saw, Cooper has revealed that he occasionally caught a glimpse of what really happened behind the closed doors of the mansion on party nights…

Young Cooper Hefner surrounded by Playboy bunnies all holding hands and laughing

Pool with a difference

One of the major features of the Playboy parties was the pool. It was part of the grotto at the house where Playmates got to swim under the sun as well as take a dip in the man-made cave. It was the perfect place for any party – no matter how wild. However, for Cooper, this was just another addition to the family home. The youngster didn’t see it as a wild party place; it was just the family’s swimming pool.

The famous swimming pool and grotto at the Playboy mansion, with Playboy bunnies all sunbathing

An extra addition

According to Cooper, people knew the Playboy Mansion “was a household for kids” and what better addition to any childhood home than having your own private zoo? Sure, celebs have kept some pretty exotic animals over the years, but Hugh Hefner wanted to take it one step further. The mansion was granted a special zoo license and is one of the only residences in America allowed to keep peacocks, spider monkeys, African cranes, cockatoos, and, of course, bunnies.

Cooper and Marston with a friend on the red carpet surrounded by two Playboy bunnies

Life with the bunnies

Unfortunately, it seems as though life around the Playmates had more of an effect on Cooper and Marston than anyone ever expected. The boys admit that growing up around all those beautiful women has made it hard to see people’s true beauty that lies beneath. Sure, it might be many teenagers’ dreams to live in a house with the Playboy Bunnies, but for Marston in particular, he says it made it difficult to build personal relationships with girls.

Cooper Hefner wearing a yellow shirt sat in the middle of Playboy bunnies showing their tails

Top choice

It looks as though Hugh Hefner has always had plans for Cooper since he was a teenager. His eldest child, and only daughter, Christie Hefner, took over as president of Playboy Enterprises back in 1982 after her father suffered a stroke. However, Christie decided to call it quits in 2009 after deciding she wanted to spend more time supporting charity. It was time for one of Hugh’s sons to step up to the plate, but which one would the millionaire choose?

Cooper Hefner toasting orange juice in champagne glasses with five Playboy bunnies

An easy decision

Thankfully, Hugh didn’t have to worry about breaking the hearts of either of his sons after discussing the company with Marston. In fact, ever since he was a child, Marston has tried to distance himself from the mansion and would only go over to his dad’s house for games nights. The pair had different tastes in women as Hugh loved blondes while Marston referred brunettes. But Hugh never wanted to give up hope that his sons would run the company together.

Hugh Hefner sat at a dinner table with his two sons, Cooper and Marston, with his arms around the boys

Turning to writing

However, Marston might not have been so different from his dad after all. Rather than wanting to get involved with the Playboy Magazine, the youngster turned his hand to his own writing. It wasn’t long before he got working on several stories, and has now released a story about zombies named ‘Bleed.’ But the youngster has tried to keep himself away from the Hefner name as his work is published under the alias Marston Glenn. Perhaps creativity is in their blood after all?

Marston Hefner with his girlfriend, Claire Sinclair and his dad, Hugh Hefner, wearing a sailor’s hat

One son down

With one son down, surely that only left one contender inline to the Playboy throne? Hugh was going to have to tread carefully if he wanted to secure Cooper as his heir. A lifetime of being surrounded by Playboy Bunnies, parties, and a multimillion dollar company? Surely that would be many people’s dreams? It was time to ask the question. Cooper admits that his father first approached him about taking over the business when he was just 19 years old.

Cooper Hefner with two Playboy bunnies in front of a 60th birthday cake for Playboy’s 60th birthday

Starting small

Cooper might not have even been an adult yet, but he was determined to take on the task of learning all about the company. However, there was an issue: Cooper was still at college. That didn’t stop him from sitting in at important meetings and being the face of their brand new London-based Playboy Club back in 2012. It seemed as though these were about to become the baby steps in the lead up to Cooper unleashing his destiny.

Hugh Hefner wearing a sailor’s hat with a Playboy bunny and his son, Cooper Hefner, by his side

Pushing together

Although Marston wanted to keep himself away from the company, he just couldn’t help but appear at all the latest press conferences alongside his brother. Could there still be hope of Marston picking up the reins of the company after all? Unfortunately, no matter how hard Hugh Hefner tried, he just couldn’t get Marston to take an interest. It seemed as though this millionaire was never going to see his sons at the helm together. It was time to focus on Cooper.

Cooper and Marston Hefner on the red carpet with Playboy bunnies wearing Union Jack outfits

Picking up the slack

Thankfully, Cooper continued to fall in love with Playboy as he learned more and more about the business and everything that came with running the enterprise. However, as Hugh’s health began to decline, Cooper was forced to take more control quicker than he ever thought. It was a decision that had been brewing for a while, but now it was about to become a reality. In 2012, Hugh announced Cooper was to be the one to take control of the company.

Cooper Hefner sat on a plush armchair with four Playboy bunnies standing behind him

Older and wiser

There might be nearly 40 years between them, but Cooper knows he always has the help of his older half-sister, Christie. After all, she worked for the company for years before successfully calling the shots for 27 years. Sure, Christie and Cooper might be entirely different people, but they both want to see their dad’s legend live on in the best way possible. Now, it was time for Christie to pass on her knowledge to the next in line to the throne.

Cooper Hefner wearing a suit standing with his half-sister, Christie Hefner, who is wearing a white outfit

Following father’s footsteps

It’s not just the enterprise that has caught Cooper’s eye over the years. This son is more determined than any other of his siblings to follow in his father’s footsteps. Back before Playboy Magazine, Hugh Hefner was enlisted in the military and began to doodle cartoons for many of the military papers. And so his love of journalism was born. So back in 2017, Cooper signed his name up to become part of the California State Military Reserve.

Cooper Hefner wearing his military uniform carrying an iced coffee and a bottle of water

Hollywood love

Being the heir to the Playboy empire has given Cooper the chance to mingle with some of the greats over the years, including many Hollywood stars. However, it was one legend in particular that caught the youngster’s eye. Scarlett Byrne. The actress rose to fame thanks after her role in the Harry Potter franchise, and the couple were official for years before Cooper popped the question. He secured permission from her dad and got the “Yes” he was hoping for. How sweet!

Cooper Hefner wearing a suit with his arm around his fiancée Scarlett Byrne wearing a floral dress]

The latest events

The couple got engaged back in 2015, and have been spotted at some of the biggest events over the years. As well as appearing on the red carpet and at acting events all around the world, Scarlett has also embraced her life as the fiancé of the Playboy heir. In fact, the pair have been snapped at some of the mansion’s famous parties – silk pajamas and all. Has Cooper found someone to share his Playboy fortune with already?

Cooper Hefner wearing sunglasses and a t-shirt with Scarlett Byrne wearing feathered bunny ears

Fatherly approval

Thankfully, Cooper got the approval he was looking for when asking Scarlett’s dad for his permission. He wasn’t the only father to love the idea of a wedding. As soon as the engagement news broke, Hugh took to Twitter to post his love for Scarlett and wanted to welcome her to the family. Perhaps he had some spare costumes for the ceremony? Although Hugh never got to see the pair walk down the aisle, they can rest knowing they had his blessing.

Black and white photo of Hugh Hefner with his son Cooper Hefner and his fiancée Scarlett Byrne in silk pajamas

Valentine’s Day special

Many stars have posed for Playboy over the years. Mariah Carey, Dolly Parton, Suzanne Somers, and Marilyn Monroe are just some of the many superstars that have appeared on the cover over the years. However, it’s not always what’s on the outside that counts. Landing a spot inside the magazine is a huge achievement for many aspiring Playboy stars, and on Valentine’s Day 2017 the magazine got a new model. Yup, that’s right, Scarlett Byrne was about to bare all.

Photo from Scarlett Byrne’s Playboy shoot where she is sat on a bed with a sheet covering her lap

Personal reasons

There are many reasons that women want to appear in Playboy Magazine, but Scarlett had her own unique views on the photo shoot. The actress posed in a silk gown wrapped delicately around her waist while standing on a balcony. However, the photo was to accompany her essay all about feminism that was going to be printed alongside her snaps. This was more than just a chance to get in front of the camera; it was time to share her views.

Photo from Scarlett Byrne’s Playboy shoot while she is looking over her shoulder with a cotton sheet around her middle

Returning to the norm

In fact, Scarlett’s photo shoot was released in the March/April 2017 edition of the magazine. While it might have seemed like just another issue for many, for the company, it was a chance to return to their roots. The magazine had ditched any nude photos almost a year before, and Scarlett’s photo shoot was going to be the first issue to feature these snaps for the first time in nearly twelve months. It was a major turning point for Playboy.

Cooper Hefner wearing a Gryffindor sweater with Scarlett Byrne wearing a pink Playboy hoodie

A closer look

So how did Cooper feel about his fiancée appearing in the magazine for millions of people to see? According to the businessman, it was nothing out of the ordinary. After all, we’re sure he’s seen it all before. Plus, Cooper went on to add that after someone has seen their mom’s Playboy photo shoot, it’s hard to be uncomfortable with most pictures. He was just excited to see the direction the magazine was about to head in.

Scarlett Byrne wearing a lace dress with her fiancé Cooper Hefner wearing a grey suit with sunglasses around his neck

No steps closer

Cooper and Scarlett might have been engaged since 2015, but it doesn’t look as though the pair are any closer to walking down the aisle. Was it the passing of Hugh that put off proceedings? Maybe they want to wait until the right time? Although the pair share plenty of snaps of their lavish lifestyle on social media, they are keeping their cards close to their chest with their wedding plans. Thankfully, there’s still time for a glamorous Playboy ceremony yet.

Photos from Instagram of Scarlett Byrne and Cooper Hefner after they announced their engagement

Trouble in paradise

Sadly, while Cooper seems loved up, Marston has been in trouble with the law thanks to his relationship with 2011 Playmate of the Year, Claire Sinclair. The pair were living together when a reported fight broke out at their home in 2012. After Claire called her parents in a panic, the police arrived to remove Marston. He was released on bail but was sentenced to a program for a year as well as being ordered away from Clair for three years.

Marston Hefner wearing a suit while sitting on the back of a car with his ex-girlfriend Claire Sinclair wearing a dress

Stepping back

Believe it or not, but Cooper took time away from Playboy in 2016. Sure, he had the empire of his dreams and was getting the chance to help add to his dad’s vision every day, but things were about to change. The magazine wanted to get rid of nudity to make room for advertisers. Thankfully, Cooper returned to reinstate their iconic photos with a modern twist a year later once the subscription numbers began to drop. At last, he could continue his dream.

Cooper Hefner wearing a suit in the middle of four Playboy bunnies dressed in matching red outfits

A great loss

Tragically, Hugh passed away from natural causes on September 27, 2017. The millionaire had been suffering from a back infection for the two years, but it looked as though he had finally lost his battle. As well as leaving behind the legacy of the company, Hugh also had his four children. As soon as the news broke of his passing, Cooper released a statement talking about all the wonderful things Hugh had achieved in his career as well as inspiring a generation.

Hugh Hefner wearing a Playboy shirt and sailor’s hat being kissed on the cheek by a blonde woman

Life with nothing

There might have been 60 years between them, but that didn’t stop Hugh from tying the knot with Playmate Crystal in 2012. Unfortunately, Hugh’s passing was about to kick everything off to a new level. The pair signed a prenup before their wedding which meant she would get nothing if he passed away. However, after his death, it was revealed the playmate would be “Taken care of” for the rest of her life – something that didn’t sit well with Hugh’s children.

Hugh Hefner and Crystal Hefner wearing matching red dressing gowns and sailor’s hats smiling at the camera

Growing the company

Cooper is set to continue the legacy that Hugh grew for so many years. The youngster admits that the photos in the magazine had become dated, but has plenty of artistic visions about how the brand will look in the future. In fact, Cooper has grand dreams of making the magazine a typical subject rather than one that is shunned by many. Playboy might have deleted their Facebook page, but they are more determined than ever to create a media empire.

Cooper Hefner walking up the stairs to an airplane with a group of Playboy bunnies wearing their outfits

Living legacy

While it might not be everyone’s idea of the perfect career, Cooper can’t imagine a life without Playboy. In fact, the businessman admits it was all thanks to a talk with his dad about honesty when he was a child that lead him to where he is today. Apparently, Hugh expressed the importance of always being honest with yourself and others around you. That way, Hugh believed anyone could achieve their dreams without hurting anyone. Cooper just wants to continue that dream.

Hugh Hefner in the middle of a line of Playboy bunnies, and Cooper Hefner in the middle of a line of Playboy bunnies