15 Photos That Will Make You Jealous Of Hugh Hefner

Hugh Hefner is an American entrepreneur who is synonymous with both success and sex. Walk almost anywhere in the world and people know exactly who Hugh Hefner is. The 90-year-old success story originated in Chicago, Illinois, where he started his business empire. Hefner was always intrigued by the magazine business and was working as a copywriter for Esquire before he walked away from that job after being denied a $5 raise. Hefner pulled all the money together that he could and took a shot on himself, starting a new magazine company called Playboy. The first issue would premiere in December of 1953, featuring Marilyn Monroe. Hefner and Monroe were a winning combination and the magazine sold over 50,000 copies almost immediately- every copy that had been printed.

After the Marilyn Monroe issue, the magazine went on to be a staple in homes all across the world. There wasn't a bathroom that didn't have a Playboy stashed away. Hugh Hefner also had to battle through years of attacks. The magazine was accused of being too risque for the time. Hugh pushed through those who would bring him down and pushed forward to become a great success. From the Playboy Mansion to the Playboy channel, Hugh Hefner has established one of, if not THE most iconic brand of all-time. Make no mistake about it, Hugh Hefner is an icon himself, a man amongst men. These are 15 photos that will make every man jealous of Hugh Hefner.

15 Oh, Golly Ms. Holly!


This literal show stopper was a big part of Hugh Hefner's life. The stunning Holly Madison caused quite a stir for Mr. Hefner when she released her tell-all book. Madison was one of Hefner's specially chosen girlfriends who got to live in the Playboy Mansion. All on her own, Madison is a beauty that make men drool. First off, according to Madison's book, all of Hefner's in-house girlfriends had to sleep with the big man. That was the price of admission to enjoy the amenities at the Playboy Mansion. In addition to having to pleasure the big cheese, Madison intimated that the women would pleasure themselves in front of Hefner. He also enjoyed the women wearing trashy outfits around him, showing off the goodies that he had bought and paid for. Hey Holly: if you want to act like a streetwalker, don't be surprised when you get treated like one. You got a career and he got you - any way he wanted. That's the price YOU chose to pay.

14 TWINS!!!


Kristina and Karissa Shannon were born in Ann Arbor, Michigan. In 2008, the Shannon Twins moved into the Playboy Mansion. That's right, what's better then one girlfriend or even a horde of women waiting on you hand and foot when you can have twins?! The beautiful pair of Shannons were added to Hefner's harem. The Shannons were brought on to appear on the show The Girls Next door. The first show they appeared in drew a whopping 2.4 million viewers. The two beautiful blondes would be a massive score and a dream come true for the common man. But Hugh Hefner is no common man and he seems to have his pick of the litter. Although the women moved out of the mansion by 2010, it's once again an example of how great Hef has had it.

13 The Playboy Mansion


Ah, the place where it all began. The infamous Playboy Mansion; a luxury every man wishes he had. Located in Holmby Hills, Los Angeles, California this amazing home was purchased by Hugh Hefner in 1959 and is now worth millions of dollars. The massive estate boasts over 22 rooms which include, but are not limited to, a screening room, three different zoo buildings, a game building, a wine cellar, a gym, a sauna, and a grand pool with a waterfall. One would never get bored living here, especially with all the babes that rotate in and out of there every day. In January 2016 however, the mansion was listed for sale and ultimately sold for $100 million. But that came with one exception, that Hugh still got to live there and work there for life.

12 The Mercedes Benz 600


The next thing us guys love besides beautiful woman is hot cars. And this Mercedes-Benz 600 Pullman Limo is quite the head turner. In fact, this car turned Hugh on so much, he got two; a 1969 and 1971. It is priced at a cool $78,100. Predictably, this car featured a divider window, a refrigerated bar, and six doors. These cars were originally built and owned by many heads of state, queens, and kings. But of course the one and only Hugh Hefner, the king of women, had to own one himself. To sit in the back of one of these cars is to feel like royalty. Riding in this classic limo and having the door opened, stepping out into the light of day for all to see, is the kind of infamy that few men ever know. Hugh Hefner is one of these men.

11 Every Start Has An End


Marilyn Monroe started it all for Hugh Hefner and Playboy. Hef is extremely appreciative of the ultimate pin-up girl. It was 1953 when Hugh couldn't resist the naked photos of Monroe and had to include them in his first ever published magazine. Marilyn holds a special place in Hef's heart. He credits her with much of Playboy's success. But in addition to crediting her with much of Playboy's start-up success, he has chosen to spend all of eternity with the blonde bombshell as well. Marilyn Monroe's final resting place is at the Westwood Village Memorial Park. Hugh Hefner bought the vault next to Monroe's so that at the time of his death he will be placed in his final resting place beside her. Hefner's world exploded with Monroe and he attributes his incredible life to her. He has chosen to share his death with her as well.

10 1966


Well, there isn't a lot you can say about this. When you are the man in the middle of this picture, surrounded by tons of half-naked women, things are looking up for you. By 1966 for Hugh Hefner, well...the world was his oyster. He was a man making tremendous strides with his business and was also single. He was an available man who made sex his hobby. He was coming off a notorious 1963 case in which he was arrested for selling obscene literature from a Playboy issue centered around a naked Jayne Mansfield. Hefner wasn't found guilty of any crime. A single Hugh Hefner had women falling at his feet left and right. Hefner admitted that during this time he was sleeping with 11 out of every 12 Playboy bunnies. Now that's the definition of a good time!

9 $$$=Parties

via The London Host

What would you do if you had $50 million to spend? Why don't we ask Hugh Hefner? Yes, that is exactly Hugh's net worth. If that seems high, you wouldn't believe that at one point Hef's net worth was over $200 million- that was at the peak of Playboy's success. Unfortunately, sales have gone down quicker then most of his playmates did. In a 2009 survey, it was reported that Hugh's monthly income was just under $300k. This included the social security he receives, pensions, retirement and income from all the rental properties he owns. Hugh Hefner, however, gave a little insight as to what he spends his millions on. You probably guessed right if you said he spends it on parties (around $25,000 a month). He also spends mega-bucks on food ($18,000) and rent ($53,593), which includes utilities, cell phone, e-mail, groceries and household supplies. And let's not forget the college expenses he has to spend on his kids ($10,130). It's not a surprise that Hugh spends more on food, babes, and parties than his own children.

8 Kimberly Conrad


Kimberley Conrad is a 5 foot 9 bombshell beauty who was named Playboy Playmate of the month for January 1988. She is now 54 and still remains smoking hot. She was one of the many wives of Mr. Hefner. These two lovebirds married in July of 1989 and remained married until 2010. However, we need to add an asterisk next to their time together. The two actually separated 11 years earlier prior to getting divorced- which means they were married just about as long as they were separated. They had two sons together and Conrad briefly turned the Playboy Mansion into a slightly more "conservative" household, meaning gorgeous women couldn't just roam the Mansion completely nude all day long; they had to at least wear thongs or laced panties. Wow- that's conservative!

7 Barbi Benton


Now we have the one and only Barbi Benton. She was born Barbi Lynn Klein in 1950 and became a model, singer, and actress.  She is also the reason why Hugh Hefner lives in the Playboy Mansion West. The two met on the entertainment show Playboy After Dark and quickly became an item. Barbi was a little nervous to go out with Hugh because he was 24 years her senior (an age difference that looks mild compared to the 50 and 60 year differences he averages with his women these days). In fact, she said to him "I've never dated anyone over the age of 24 before." He responded, "That's ok, neither have I." Although she had appeared on the cover of Playboy four times, she was never named Playmate of the Month. That's OK Barbi, you are still #1 in our hearts and ridiculously beautiful!

6 Izabella St. James


Here's Ms. Izabella St. James, folks. Born September 1975, St. James is the author of the memoir Bunny Tales: Behind Closed Doors at the Playboy Mansion. This gem not only has beauty (insane beauty BTW!), but brains as well. She graduated high school with an award for academic excellence and proceeded to finish law school. St. James met Hef when she went out with a group of friends at a nightclub one night. It wouldn't be long before she moved into the Playboy Mansion and became ONE of Hugh Hefner's "official" girlfriends. As previously stated by Holly Madison in her own tell all book, Hef had some weird things going on at the Mansion. St. James came out to diss Holly and said that Holly was crazy and obsessed with Hugh and said everything that she revealed wasn't true. Now, that's one hot cat fight that I would like to see!

5 Karen Christy


Man would she have burst my bubble! This 37C-24-36, 5' 6" blonde bombshell beauty was born March 11, 1951. But don't let the age fool you! She is definitely a MILF today. Christy met Hef while he was traveling through Texas and the two quickly became romantic. Hugh actually described his relationship with Christy as "one of his most passionate ones--while it lasted".  She was named Playmate of the Month in December 1971. Christy was a self-professed party girl. She loved men and she loved to party- which is probably why she got along so well with Hef. Christy actually used to be a bunny at the Playboy Club in Chicago. Christy has a very creative side. She loves the arts and enjoys painting and sketching. This heavenly blonde was quite the package in her day.

4 Bridget Marquardt


Flower power anyone? Bridget was born in Tillamook, Oregon. Bridget was never a Playboy Playmate, which almost seems like a crime. But she was super-hot and appeared naked in the magazine. Bridget grew up in California, attended California State University, Sacramento, and graduated with a BA in Communications. In 2001, she obtained a Master's Degree in Communications, showing that this insanely beautiful blonde is no bimbo. Although Bridget was unable to become a Playmate after two test shoots, she was invited to the Playboy Mansion and became a regular guest of Hef's. She was invited to move into the Mansion and became one of Hefner's girlfriends in late 2002. Bridget was able to achieve some level of television and movie success, parlaying her relationship with Hefner and her beauty on screen with a variety of small roles. We like her because we think she's hot.

3 Shannon Tweed


Oh, man. Unless you have lived under a rock all of these years, you have heard of the beautiful Shannon Tweed. Tweed married KISS front man, Gene Simmons, in 2011, who finally made an honest woman out of her. But long before she met the tongue of Simmons, Tweed lit up the entertainment world as one of the sexiest and most desirable women around. She was the "Queen of Erotica"- one of the industry's most successful actresses of all time. Tweed was chosen in 1981 to be Playmate of the Month for November. Then, in 1982, Tweed was named Playmate of the Year. Shannon and her sister, Tracy, even appeared together in a Playboy spread! Tweed was one of Hef's favorites and resided in the Playboy Mansion for 14 months as Hugh's "partner." So hot!

2 The Bunny Jet


Hugh Hefner- creator of the mile high club? I think so. Only Hugh would own a jet decked out with everything imaginable. This plane was the kind of air travel fit for a King. Hefner's jet is probably as big as most of our houses. The jet includes a living room, shower, and a mega bedroom (undoubtedly where no one has ever slept). All the females that were employed were trained by Continental Airlines but they weren't your everyday stewardesses. They greeted Hugh with big signs with their fuzzy tails erect and ready for the man, himself. Let's not forget their tight black leather mini dresses- although, come to think of it, that would be near impossible to forget. Hugh paid a whopping $5.5 million for the designer jet, which was a massive expenditure back in the day. But to him, that was just chump-change.

1 Crystal Harris


Hello Miss Crystal! What a lucky guy Mr. Hefner is. Hugh landed this beauty as his wife in December 2012.  Named Playboy Playmate of the Month in December 2009, Crystal Harris began her career as a model and was quickly discovered by the Playboy team. After Hefner's former #1 girlfriend left him, Harris joined Hefner in the Mansion along with his two other girlfriends, the Shannon twins. Shortly after being named Playmate of the Month, Crystal began dating Hugh and they were engaged- uncharacteristically quickly for Hef. However, Crystal got a whiff of the old cold feet after posing in Playboy's June edition, which was later referred to as "The Runaway Bride." She left and wasn't going to return until she realized that Hefner was her meal-ticket and she really had no other options out there. Harris soon came to her senses and the two wed in a small ceremony. He was 86 and she was 26. Talk about robbing the cradle- great grandpa style!

Sources:  biography

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15 Photos That Will Make You Jealous Of Hugh Hefner