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15 Photos of Hugh Hefner’s Millionaire Lifestyle

High Life
15 Photos of Hugh Hefner’s Millionaire Lifestyle

What would you do if you were a multi-millionaire like Hugh Hefner? Everyone dreams of having a big mansion, one of the most expensive hotel suites in the world, traveling by private plane, and partying all the time. But this Playboy mogul’s most prized possessions are his bunnies. With too many playmates living at his place, celebrities on the cover of his magazine, and six girlfriends in his bed, Hugh Hefner is living every man’s dream. Now, at 91 years old, nothing is keeping this gentleman from flirting with the ladies until his final day. But is it really the kind of life women want to be living, too?

All the girls in the Playboy mansion seemed happy, but unfortunately, one of his ex-girlfriends reported that they weren’t joyfully hopping everywhere. Hugh Hefner was certainly pleased, but the playmates were more like full-time sex workers for him. Nobody admitted to having sex with him or ever dared to say bad things because they didn’t want to get in trouble. But one little bunny spat out her carrot and opened her mouth to talk about what was truly happening there.  The playboy’s life might look good but, in the industry, this is nothing but appearance. This is what you can afford when you are a multimillionaire: a mansion, tons of girls, and an illusion. No matter what, many men wish they lived a dream life just like his.

The playboy always had the best job to make sure dozens of beautiful women surrounded him as the editor-in-chief of Playboy Magazine, but Hugh Hefner finally found the woman who is the most precious to him. She made one big achievement: being the only woman in his bed for a night, leaving the other playmates outside of their room. However, marrying a millionaire comes with some disadvantages, including the old age, but also an unusual agreement. Make sure you read this list to find out what it is. Today, we’ll be showing you 15 photos of Hugh Hefner’s millionaire lifestyle:

15. Gentlemen Prefer Blondes

Hugh Hefner didn’t have one, or two, but usually six or seven girlfriends at the same time. Why stay with one woman when you can afford to spoil as many as you want? Because of love? That’s why the businessman preferred a sexual relationship with many bunnies.

Holly Madison was one of the playboy’s girlfriend and wrote a book to tell the world about her experience. She told Cosmopolitan that, even though Hef said he wanted the girls to get along together, he made sure there was drama so he could feel relevant, wanted, and desired. If the bunnies were friends, they could have stood up together to get what they want, and Hefner didn’t want that. He was insecure and manipulating them was a way to control what was happening in their relationship.

Sometimes, less is more, and the editor-in-chief of the famous magazine doesn’t seem to understand that. If he wasn’t looking for quantity, he’d probably be able to enjoy a better quality of woman: the kind of woman who is happy.

14. On Top of the World

When you are on vacation, you might like to treat yourself to a luxurious hotel with a beautiful view of the sea and room service. But what if you already have everything someone could ever dream of? You have to be looking for even more luxe!

Some people earn $40,000 a year, but this is what it costs to spend one night in this suite at the Palms in Las Vegas, making it the second most expensive hotel in the world. The two-story 9,000 square foot villa cost $10,000,000 to build and is owned by Hugh Hefner. It includes a rotating bed, a wall Jacuzzi, a terrace, a sunbathing area, indoor water features, a gym, a media room, a massage and spa room, a glass elevator, and much more. Hugh Hefner can stay there for free with his lucky girlfriends when he visits Las Vegas.

If you ever want to feel like the famous playboy for a weekend, you can simply sell your house to afford three nights in this suite. But remember that you’ll always have something rich people don’t have anymore: not taking anything for granted.

13. Having Fun With Celebrities

The editor-in-chief is part of the rich and famous, so it is not surprising to see him hanging out with celebrities. The most beautiful ladies loved to attend lavish parties to meet celebs, and the playboy was really happy to mingle with these sexy women.

Not only does he meet celebrities during the parties, but he also lived with them! Hugh Hefner told Vanity Fair that his favorite guests were actor Tony Curtis and cartoonist Shel Silverstein. A woman also told XO Jane that she and her friends met Snoop Dogg,  Three 6 Mafia,  Corey Feldman, David Hasselhoff, Bill Maher, and Pauly Shore at the parties. And don’t forget about the ladies! Celebrity bunnies and playmates were hopping all over the place. It is even believed that there were a series of underground tunnels connected to the mansion and leading to surrounding celebrity homes. The tunnels were closed in 1989, but it still shows that Hugh Hefner had a special relationship with celebs.

Some people wished they would one day get the chance to meet their favorite celebrities and Hugh Hefner made this wish come true at every party. Luckily for the women, they only needed to be hot and sexy to attend these events.

12. Hugh Hefner: The TV Series

It’s not the first time that a movie has been made to tell the life of a millionaire, but editor-in-chief Hugh Hefner is so rich that many films, documentaries, and TV series were created to show what the playboy life really is.

In April 2017,  Amazon Original presented the TV series American Playboy: The Hugh Hefner Story. The entrepreneur’s story is told as he remembers it from the launch of the first Playboy Magazine in 1953 to sixty years after. It shows the impact it had on culture, as Hefner became a social justice advocate and a target of the conservative movement during the sexual revolution. With archival footage, interviews, and cinematic reenactments, this is the perfection combination of a man’s memory and the legendary life he really lived. But what is even more interesting is that you will get to enjoy the view of beautiful women just as much as the playboy himself did.

Who is the luckiest? The real Playboy or the actors who were paid to live his life for a moment? We bet that many men would have like to play that role. However, it takes a great talent to portray a man who acts like a gentleman but hides a bitter personality.

11. A Great Catch

What does a rich man do during his free time? It seems like Hugh Hefner is always partying in the Playboy mansion. And even if he leaves his luxurious life for a moment, the Playboy makes sure there is always a woman by his side.

Being a playboy is a full-time job, and Hugh Hefner became a multi-millionaire by being one 24/7. According to him, there was no better vacation than staying at the mansion. He told Vanity Fair that it is because, it’s the place everybody wants to go to, and I agree with them. Everything that you want is here.”  His favorite kick back at home was watching movies three nights a week, and his favorite room was – you guessed it – the bedroom. However, don’t think this was only to have sex in his bed three times the size of a regular bed. He also liked to watch movies in his room or simply work on his own.

Now that he is getting older, Hugh Hefner’s life is much calmer, but he never stops enjoying life. The editor-in-chief of Playboy wanted to entertain men, but he also made sure that he and those around him would always be having fun.

10. The Hottest Cover Girls

The editor-in-chief of Playboy is lucky enough to present some of the most popular celebrities on the cover of his magazine. Who thought Marilyn Monroe would be the first Hollywood actress to take off her clothes to make the cover of the magazine?

In 1949, a young Marilyn Monroe posed nude for Tom Kelley to earn $50 to pay her rent. She wanted to make sure no one would recognize her, but everyone realized it was her years later when Hefner bought the picture for the first edition of Playboy Magazine. Marilyn Monroe was the first Sweetheart of the Month, but it was not something to be proud of at that time. She was the first known actress to pose nude, and many people thought this would ruin her career. Fortunately, the public forgave her, and the actress became one of the most beautiful sex symbols at that time.

Years later, many of the hottest celebrities have been proud to be on the cover of the magazine, including Kate Moss, Kim Kardashian, Lindsay Lohan, Madonna, Carmen Electra, Pamela Anderson, and much more. All of this thanks to Hugh Hefner!

9. The Beautiful Years 

During the 70s, being featured in the centerfold of the Playboy magazine was the pinnacle of achievement for a young model or actress. Men’s favorite entertainment was becoming more and more popular as Hugh Hefner was living the dream.

It was the years of sex, drugs, and rock n roll! Hugh Hefner made sure he enjoyed all these things at the same time. Holly Madison reported she was once offered a quaalude on her first night out clubbing with him. She told him that she didn’t do drugs and he answered: “Usually I don’t approve of drugs, but you know, in the ’70s they used to call these pills ‘thigh openers.'” It seems like a lot of thighs opened at that time for the playboy when it was not considered as something illegal.

The seventies are far behind him, but Hefner never stopped living in those years. The 91-old-man never grew up, and the women surrounding him are just as young as they were before as he is still partying with the most beautiful playmates he could ever find.

8. Don’t Stop The Party

The parties are what made the Playboy Mansion famous since the 70s. This is where everything you ever dreamed of could happen: meeting celebrities surrounded by the hottest girls wearing sexy outfits. Or was it just an illusion created by the drugs?

How do you get invited to Hugh Hefner’s party? You had to be famous or send a picture of you in a bikini if you were a girl, as reported by Melissa Stetten for XO Jane. If you passed the test, you were hot enough to party in the mansion and meet celebrities. At the party, people were surrounded by a sea of flesh and boobs, and some girls were even just wearing body paint. There was a big dance floor, the alcohol was free, and the pool was open to anyone who wanted to take off even more clothes. And if this wasn’t enough for you, there were also an after party at another millionaire’s house and pool parties during the day.

Unfortunately, Hugh Hefner had his last Midsummer Night’s Dream party at the Mansion in 2016. His neighbor Daren Metropoulos bought the house. We don’t know yet if there are going to be more parties, but we hope we have what it takes to be invited!

7. A Happy Bunny In Bed

Hugh Hefner’s girlfriends have to do what every girlfriend does… if you forget about the respect and the consent. No matter how old he is, the playboy never stopped having sex like a rabbit with all his beautiful bunnies.

Even though he publicly denied it, each girlfriend had to participate in Hef’s bizarre bedtime ritual, as Holly Madison said in her book. The girlfriends and all the girls he could recruit wore matching pink flannel pajamas.  They put on a show and kissed each other to excite him while he pleasured himself in bed. It wasn’t the kind of sex you’d usually imagine. Holly remembers: “There was zero intimacy involved. No kissing, nothing. It was so brief that I can’t even recall what it felt like beyond having a heavy body on top of mine.” And when it was even dirtier, there was always humping more than one bunny in his bed. It was not possible to count the number of girls who went through the revolving door in his bedroom because there were too many.

Unfortunately, Madison says that all the girls hated this bedroom routine. Hugh Hefner might be the greatest playboy in the world, but that doesn’t make him the best partner in bed. Hundreds of women could tell you about it.

6. The Playboy Mansion

The Playboy Mansion is probably one of the most famous icons after the playboy bunny. It became famous in the 70s when the media started reporting about Hugh’s crazy parties in the 21,000-foot house built in 1927.

What happens in the mansion stays in the mansion, including the girls. Holly reported that bunnies didn’t really have the right to have a life outside of Playboy, and this rule was even more important for the girlfriends.  The gate around the house was not meant to keep people out, but to keep them in. Twins Carla and Melissa Howe told The Mirror that it was like a prison. The girls had to come back to the mansion before 9 p.m., they couldn’t invite friends to the mansion, and no male visitors were allowed. They had to show everything in a good light on social media and never look drunk in a picture. And once they broke the rules, they were out. They could never come back.

In 2016, the Playboy Mansion finally sold for $100,000,000, even though Hef first asked for $200,000,000. No one knows what the new owner wants to do with it, but we hope it will be just as wild, and more enjoyable than it was before.

5. Forever Young

Hugh Hefner is so rich that he found a way to buy the elixir of life. Surrounded by young, beautiful women for several years, the 91-year-old man will stay forever young. He loves taking care of his girls so they can offer him their bubbly energy in exchange.

The playboy knows what is trending right now. He is not shy to appear in a Snapchat video with his wife Crystal or dress as Robin Thicke while she dances on him like Miley Cyrus for Halloween. Even though his body might be old, his heart will always be 25 years old, just like the women he likes to party with. No one can stop him… as long as he has Viagra and someone to hold to make sure he won’t fall when he walks. As Carla Howe, an ex-playmate told The Mirror, It’s like being with a grandad. Not long ago they called in the nurse because he’d had a fall in the grotto.”

Maybe that’s the secret of immortality: living every day like it was your last one. After all, now that he is getting older, it won’t be long until he has to face that final day. When the time comes, he will be proud to say that he lived life to the fullest.

4. The Playboy Club In Chicago

Ever wished to have your own playmates? With bunnies as waitresses, the Playboy Club in Chicago is the best place to make your fantasies come true. You don’t have to only dream of what you see in the Playboy Magazine; now you can actually live it.

The Playboy Club opened on February 29th, 1960. Hugh Hefner himself told DNAInfo that his initial idea was to recreate for club members the fantasy that was reflected in the pages of the magazine. As it turned out, we put it all together, and they brought the fantasy with them.” When club members were present, their nameplates would appear on the directory in the front, so everyone knew if celebrities, VIPs, performers, or even Hefner himself were there. At the time the club was created, nothing else represented the good life like this place did. This concept was soon replicated in the Playboy Clubs all around the world so men could feel home no matter where they went.

The beauty of Hefner’s fortune is that he shared it with the rich and famous around him. What was all his money worth without friends and ladies by his side? The Playboy had a dream and knew that any other men would be captivated by this fantasy, too.

3. All The Playmates 

Hugh Hefner’s most prized possessions are his playmates. Any millionaire can buy a mansion or a plane, but women are priceless. There was enough place for as many ladies as he wanted in his 29-room Playboy mansion and even more at the parties!

Madison even recalls that some girls who lived in the mansion wanted to recruit as many people as possible. And that have to be the most beautiful, Hefner made it clear that he wanted them to wear over-the-top trashy outfits. Hugh provided each girl a $1,000 weekly clothing allowance to make sure they looked the best. Their life at the mansion also included unlimited beauty services and plastic surgeries, the most popular being boob jobs, nose jobs, and liposuctions. This Playboy is not only choosing the hottest girls, but he is also sculpting them with his money.

Being a playmate is a dream job for anyone who wants to work in the adult entertainment industry. However, don’t forget that this is a job, and not a love story, as the only thing Hugh Hefner has to offer is his money. But sometimes, that’s all women want.

2. Jet Bunnies On Board

Hugh Hefner loved to ride bunnies, but the Big Bunny was his favorite. Bought in the late 1960s, this customized private plane took the playboy, his jet bunnies, and celebrity guests all around the world on an amazing sexual adventure.

The $5,000,000 Big Bunny was only used for six years but it is something Hef will always remember. The plane was a symbol of the sexual revolution as the mini skirt had just arrived and Hefner believed the sky was the limit.  It was the only plane painted black at that time and spotlights were installed on the wing tips to make sure that the Big Bunny would always stand out. The 38-passenger plane was like a floating apartment with a bedroom, a living room, a dining room, and everything he needed for entertainment. It also had a fully stocked bar and a club where parties often took place. With this crowd pleaser shining in the sky, Hugh Hefner was literally on top of the world.

Unfortunately, Playboy sold the Big Bunny in 1975 and it was used as a commercial airliner until 2004. When asked if he missed the plane after all these years, Hugh Hefner replied, “only when I fly.'”

1. The Beautiful Young Wife

No matter what, it’s hard for the ladies to not fall in love with Hugh Hefner when he acts like a gentleman. The bunnies wanted to become the only one girlfriend. And when one finally succeeded, he wanted to make sure she was really interested in him

Before their wedding day on December 31st, 2013, Crystal Harris signed an “ironclad” prenup, as reported by US Magazine. Hugh Hefner wanted to make sure his estimated $43,000,000 fortune would be promised to his children, the University of Southern California, and a variety of charities. His then-fiancée wasn’t added to his testament. This is probably one of the reasons why she first broke up with him, but she finally accepted his plan and decided to marry him anyway. There is at least one thing Crystal can be proud of: she was the only woman having sex with him. This is so rare that it must be worth a lot.

Hugh Hefner wanted the bunnies to have everything they want… as long as they stayed with him. Unfortunately, breaking up with a playboy is not only leaving a man, but also a home, and more money than you could ever imagine.

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