Hugh Hefner, Was He The Play Boy We Think He was?

The controversial culture icon will forever be mostly remembered as the founder of the infamous Playboy magazine. However, there is more to Hugh Hefner’s history and life than just nude bunnies and extravagant parties at the most famous mansion in the world. In fact, he had a pretty low-key life before he became a millionaire.


The hedonist mogul did not only change the face of journalism, he helped bring sexuality into the mainstream debate and conversation. Huge Hefner, whether you’d like to admit it or not, was a revolutionist. These are some of the most interesting and little-known facts about the Playboy creator and family man who passed away peacefully at his mansion.

A Conservative Boy

 The Chicago-born grew up at a Methodist home to religious parents who worked as school teachers. Let’s just say that growing up in a conservative home as Hefner’s, no one ever thought that one day Hugh would become such an extrovert and the owner and founder of the most sexually expressive magazine in the world.


His romance with journalism actually started at the age of nine when he first published a local newspaper. He sold the neighborhood paper for just a penny. Young Hefner was also very much into cartoons and when he was a teenager, he became interested in the men magazine, Esquire.

Mamma Helped Him Build His Empire

Hugh’s love for Esquire magazine soon turned out to be more than he expected as he was hired as a copywriter for the magazine. Hefner who graduated with bachelor of arts from the University of Illinois at Urbana Champaign, also minored in creative writing. When the paper rejected Hefner’s tiny raise of $5, he knew he had better things coming his way.


He knew he could make something even greater than the magazine he was working for and started collecting the money to launch Playboy. What’s interesting is that his conservative mother was one of the loaners, she loaned her son $1,000 to follow his dreams.

Breaking Records

Sure, everyone knows that set a precedent when he founded the controversial magazine, but he also made some other groundbreaking achievements. In fact, Hefner holds a Guinness World Record. He was the longest-running Editor-in-Chief of a magazine. Hefner approved each and every issue until his final days.


Every picture, every paragraph and every word, it all had to be approved by Hefner himself. Does it mean he couldn’t trust his editors? Or perhaps he was just a little bit of a control freak? In any case, he must have done something right.

 He Was Cheated On

The man, who pretty much made millions and built an empire around stunning ladies, had one unfortunate experience with the woman who was his childhood sweetheart. Mildred ‘Millie’ William was Hefner’s first wife. However, Hefner’s first stint with marriage wasn’t great.


Hefner found out that his beloved wife had cheated on him before they were married. Despite this heart-breaking revelation, the two tied the knot in 1949. Hefner has admitted many times in the past that finding out about his then-girlfriend’s affair was the most devastating moment of his life. Perhaps, that was the moment that forever changed his attitude toward life and women specifically.

Me and Marilyn, Till Death Do Us Part

It seems like Hugh Hefner’s and Marilyn Monroe’s life will forever be intertwined. The very first issue of Playboy magazine featured the famous actress in its centerfold. The 1953 issue sold more than 50,000 copies.


The Chief-editor of Playboy, Mr. Hefner himself, must have been seriously impressed with Monroe that he decided in 1992 to buy the crypt right next to hers at the Westwood Village Memorial Park for $75,000. It is believed that the legendary publisher will be laid to rest next to the iconic pin-up girl.

The Women He Called ‘Wifey’

It’s sometimes hard to believe, but even Hugh Hefner, the ultimate Play Boy, has settled down more than once throughout his life. Perhaps, he too was hoping for that nice family life that most people are looking for, with one partner.


While Hefner did have multiple girlfriends, he also managed to find love and even make it official. He married his second wife, Kimberly Conrad in 1989. Conrad was also Playmate of The Year and she met Hefner at a time when he was tired of all the partying and after having a small stroke. The two have two sons, Marston and Cooper. Hefner has two more children from his first marriage.

Holy Holly

One of the most famous relationships Hefner had in the mansion was with former Playboy Bunny, author and TV personality, Holly Madison. In her memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Madison reveals some of the darkest secrets about Hugh and life at the mansion.


For instance, Holly talks about Hugh Hefner’s weird and controversial mansion rules. One of these rules including the Playmates having to change into flannel PJ’s before it was time for bedtime.

 Bedtime Stories

 Hefner’s reputation and the way he used to treat women was always one that was questioned. While life at the mansion seemed wonderful on the outside, the story was quite different from within. According to Madison’s memoir, there were some pretty strict rules.


Hugh liked to be in control, as it turns out, after all he did have many girlfriends to look after. Hefner was very strict about curfew and he asked the girls to be home by 9 PM. He would also, allegedly, create unnecessary drama among the girls by switching around the policies making it seem like he is favoring one of the other.

 Family Matters

 It must have been quite confusing growing up with a father who is famous for owning the most beautiful house in the world, literally. On one hand, it could seem like every boy’s dream to have Hugh Hefner as a father, on the other hand, things could go really wrong really fast.


It was rumored that his sons who were only 9 and 10 years old at the time, had to share their bedroom with a Playmate when they came over. You can only imagine how weird it must have been to see all kinds of toys lying around the mansion’s floor.

It’s Crystal Clear

Hef met his third wife, Crystal Harris in 2008 during a Halloween party that was taking place at the mansion. The two called off their wedding in 2011, just a few days before the planned wedding day. When they were apart, Harris was interviewed on a famous radio show where she revealed some interesting facts about their relationship.


Harris revealed live that she was not attracted to the Playboy mogul. Apparently, her comments were not so bad in Hugh’s opinion as they reconciled and eventually tied the knot in 2012. In terms of his fortune, Crystal is not in line to inherit his millions of dollars.

Crystal Harris: 60 Years Younger Than Hugh

One of the most interesting things about the marriage between Crystal Harris and Hugh Hefner was the enormous age difference between them: 60 years. Not only was Hugh Hefner old enough to be her father, he was old enough to be her grandfather. Perhaps, even her great-grandfather!

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According to reports, Hugh Hefner said that his marriage to Crystal worked because they had “true love” between them. It seems like the third time was the charm for Hef, because this one finally worked until the inevitable happened.

Being the Wife of Hugh Hefner

Try to imagine being the wife of Hugh Hefner. First, it doesn’t matter how gorgeous you are, you have to know that Hugh was going to have affairs with other women. That was always part of the deal. You also had to contend with a parade of other women in the house, generally scantily clad women, many of whom would sleep over at any given time.

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For Crystal Harris, now Crystal Hefner, she was originally a playmate who spent time in the home. She even appeared on The Girls Next Door. So, she certainly knew what she was getting into when she married Hefner. Oh yes, she also had to contend with Hef’s second ex-wife, who lived right next door.

The Playboy Mansion

If you were married to Hugh Hefner, or one of his girlfriends, you got to live in the Playboy Mansion. Located in Los Angeles, the mansion has 22 rooms including a wine cellar, pool, aviary, basketball and tennis courts, and movie theater. Built in 1927, the home was eventually purchased by Playboy Enterprises.

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Hugh Hefner didn’t actually own the Playboy Mansion, he rented it from Playboy Enterprises, Inc. According to records, he paid just over $1 million a year to stay there. The corporation paid for everything else, including all of the operating expenses.

Work and Play in the Playboy Mansion

Since the home was owned by Playboy Enterprises, Inc., the entire home wasn’t at Hugh Hefner’s disposal. In fact, only a part of the home was actually used as living quarters. The rest was used for events, corporate activities, television production, and as a magazine photo shoot setting.

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So, for Hugh Hefner, he could conduct his work and his personal life right in the same place. This also meant, of course, that work was never far from this well-known workaholic.

The Rules of the Playboy Mansion

We have already mentioned that there were rules if you lived in the Playboy Mansion. For example, if you lived there as one of Hugh’s girlfriends, you had to be available for bedroom activities whenever he was interested.

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Another “rule” of living in the Playboy Mansion was that you got an allowance: a cool $1,000 a week, which sounds awesome, right? Well, it was, except you were only allowed to buy clothes with that $1,000.

Other Mansion Rules

Those were not the only rules of living in the Playboy Mansion, of course. Another rule that the girls had to follow is the rule of silence: when Hugh was giving an interview, you could be seen, but not heard.

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Though that wasn’t necessarily a good rule, there were perks to living in the Playboy Mansion, too. For instance, you got full use of a fancy sports car whenever you want. However, you couldn’t take it with you when you moved out, so hopefully, no one got too attached.

Even MORE Rules at the Playboy Mansion

Yes, there are still more rules that must be followed when you live in the Playboy Mansion. For instance, you could get as much plastic surgery as you wanted for free: but, you weren’t allowed to interact with other men during parties at the house. You always had to stay by Hef’s side.


You were also expected to stick to a pretty strict routine when living at the Playboy Mansion, and you had your daily activities arranged for you. It’s said that this was so none of Hef’s girlfriends could meet other guys. Plus, you had a 9:00 PM curfew.

A Playmate’s View of the Mansion

In 2010, Izabella St. James, a former playmate, didn’t have very nice things to say about the Playboy Mansion. In fact, she said it smelled, was dated, and felt “old and stale.” She said that the resident dog, Archie, would often relive himself on the carpets, so the scent of urine wafted through the air. She also claimed that the furniture in the mansion was mismatched and random.

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Izabella St. James further said that the mattresses were old and stained, and that the sheets were in need of replacements. She explains more about living in the mansion in her book, “Bunny Tales,” which was released in 2006.

Hugh Buys the House Next Door

As mentioned, Hugh Hefner bought the house next door to the Playboy Mansion. He did this so that his estranged second wife, Kimberley Conrad, could remain close with his sons, Marston and Cooper, who were only 9 and 10 at the time. It’s almost identical to the Playboy Mansion, but smaller.

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Reportedly, Hugh Hefner paid several million dollars for the home. His family remained in the home until 2009 when it sold. The asking price was $28 million, but it eventually sold for $18 million.

Hugh Hefner Bought Another Home, Too

In 2002, Hugh Hefner bought another Los Angeles home, too. In this case, it wasn’t next door, but just down the street. Known as the “Bunny House,” this home was a place for guests of the Playboy Mansion to get away from the hustle and bustle of the main house.

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Hugh Hefner’s playmates could use the Bunny House, as well as certain guests of the Playboy Mansion. Hugh kept the house until 2013, when it was put on the market for $11 million.

The Playboy Mansion is Sold

In 2016, Playboy Enterprises, Inc. decided that it was time to part with the Playboy Mansion. So, they put it on the market for $200 million and one condition: whomever bought the property had to allow Hugh Hefner to continue to rent the mansion for the remainder of his life.

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The person who bought the home was familiar to Hugh Hefner. It was Daren Metropoulos, who is one of the owners of Hostess Brands. That’s not how Hugh knew him, though. Daren was the buyer of the home Hugh sold in 2009, which housed his ex-wife and two sons. He ended up buying the Playboy Mansion for $100 million.

Hugh Hefner and Charity

It often surprises people that Hugh Hefner was such a charitable man. He was involved with many charities including Much Love Animal Rescue and Children of the Night. He also donated $27,000 to help repair the Hollywood sign, and gave $100,000 to the University of Southern California.

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Hugh Hefner was also very interested in politics and often donated to and raised money for the Democratic Party. He claimed in 2011 that he was going to register as independent, however. In 2012, though, he supported the re-election of President Obama.

A Family Affair

The Playboy empire is certainly a family affair. Hugh Hefner’s daughter, Christie, was the CEO of Playboy Enterprises, Inc. for 20 years, and she worked for the organization for 30. She stepped down in 2009 and focused her time on charity work. Her brother, David, is rarely seen in public and he prefers a quiet life.

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Christie Hefner has helped to raise tens of millions of dollars for organizations such as CORE Chicago, which is an outpatient center for AIDS patients. She has appeared several times on the Forbes’ 100 Most Powerful Women in the World list, too.

Hugh’s Other Children

In addition to Christie and David, Hugh has two younger sons, who we mentioned earlier, Marston and Cooper. Marston has gotten into a bit of trouble over the years, including getting arrested for attacking his girlfriend, who was a Playboy Bunny.

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Hugh Hefner’s youngest son, Cooper, is the Chief Creative Officer of Playboy Enterprises, Inc., and he is in the California State Military Reserve. At 26-years-old, he is said to be Hugh’s choice to take over the family business, and will be the public face of the Playboy of the future.

The Legacy of Hugh Hefner

Hugh Hefner passes away on September 27, 2017 at the age of 91. He leaves behind his wife, Crystal, and four adult children. His assets will be split between those children, and it is believed that part of his estate will be donated to the University of Southern California film school and to various charities.

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It is believed that Hugh Hefner has a fortune of about $43 million, but his widowed wife will not receive any part of it. Media reports claim that she signed a prenuptial agreement when they got married saying that she would get $0 when he passed away.

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