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91 Years: 24 Pics Of Hugh Hefner That Will Make Any Man Jealous

Hugh Hefner has died and he is being mourned by friends, family, and fans all over the world, most of which call him a hero. However, the famous magazine founder is no hero considering he built an entire empire on misogyny, but he is iconic for his contributions to pop culture over the past several decades. Say what you will about Hugh but he managed to stay relevant since the 50s and created what is considered the Holy Grail to pubescent males everywhere: Playboy. The first issue of the magazine was published in 1953 and was funded in part by a $1,000 loan from Hugh's mother. Imagine getting a loan from your mom to start the smuttiest magazine of the era!

The magazine became famous for its centerfolds featuring women wearing bunny ears and not much else. These women were named Playmates and thousands of women have vied to become Playmate of the Year. In order to be considered as one, models would send in photos of themselves with a "girl next door" quality which is what inspired the name of the reality show The Girls Next Door which focused on the lives of Hefner's girlfriends who live with Hugh in the Mansion. Kendra Wilkinson, Holly Madison, and Bridget Marquardt appeared on the show for all six seasons and saw various degrees of fame after the show ended in 2009. Madison is known for her memoirs in which she airs Hugh's dirty laundry and reveals him to be a womanizing and misogynistic pig. Wilkinson, on the other hand, has never said a bad word about Hugh and has always come to his defense, especially against Madison's attacks.

Despite all of the womanizing, allegations of assault, and general creepiness, Hugh has been a fixture in popular culture for over six decades and he has managed to woo hundreds--maybe thousands--of beautiful women over the years. Here are just a few photos of his adventures and exploits that may make you feel a pang of jealousy.

24 No Family, No Problem

TV Guide

Before Holly Madison was writing tell-alls about her elderly boyfriend, Holly was on The Girls Next Door which ran from 2005 until 2009 on E!. However, in the last season, the three girls had already broken up with Hugh but were contractually obligated to appear in the sixth season. Hef replaced his girlfriends with younger girls (something he was very accustomed to doing at this point). Madison explained in the fifth season that she was unhappy with the fact that she would never be able to marry Hugh or start a family with him (ew) and once she left to start a family with her now-husband, the Stockholm syndrome seemed to wear off and she decided to tell the world the dark secrets of the Mansion. Some of Hef's secrets included a bizarre need to control his girlfriends in every respect, from their bedtimes to the color of their bedroom walls.

23 Mr. Worldwide

The Mansion has housed many celebrity guests over the years (and decades) but who is a more distinguished guest than Pitbull, aka Mr. Worldwide, himself? Being a guest at the Mansion was a coveted honor (at least to men who enjoyed watching women prancing around in stockings and bunny ears) and the girls had the responsibility of "entertaining" the guests. Most of the time, this kind of entertaining went on in the bedroom. Some of the entertaining, however, involved illegal activity. Hef made it seem like the Mansion was a man's heaven and it was--at least for misogynistic men. Though Hef wanted to keep up the appearance of extravagance and elegance and not trashiness, the Mansion was the Mecca of sleaze.

22 The Big Bunny

via Reddit

Hugh's private jet was like the Mansion but in the sky. His plane was a Jet Black DC-9 which he named "Big Bunny" and he used it to carry his various girlfriends and famous friends. The jet featured a theater, multiple lounges, full bathrooms with showers, and a round water bed--classy, right? The women seen above were called Jet Bunnies and they were not only responsible for looking good, they were also required to serve as flight attendants. Their uniforms were designed by designer, Walter Holmes, who put together a trashy ensemble of leather dresses, white scarves, and black go-go boots. Hef occasionally lent out his jet to his famous friends such as Elvis Presley, Sony and Cher, and Yul Brynner. Due to the decline in sales in the 1970s, the jet was sold in 1975.

21 Blondes Have More Fun

Hello Magazine

Despite the fact that one of his long-term girlfriends was a brunette (seven years was a long time for the Playboy founder), Hef loved blondes. Pamela Anderson was one of many blondes that Hef loved and she was named Playmate of the Month in 1990 which helped her to start landing roles in Hollywood. The Baywatch star appeared in Playboy for 22 years and has appeared on more covers than any other model. She also was the last model to pose in her birthday suit in the magazine after they announced that they would no longer feature naked women. Since it was Hef who helped to get her noticed in Hollywood, she always felt a strong connection to him. Upon learning of his death, she filmed a video of herself in bed wearing lingerie, as she wiped away her mascara-infused tears, she whimpered, "Goodbye Hef." Weird.

20 1 Night With Paris

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Pamela Anderson may have been the most iconic blonde in the 90s but Paris Hilton was the most iconic blonde in the early 2000s and although she first rose to fame with the leak of her scandalous tape, 1 Night in Paris, she was forbidden by her mother from appearing in a centerfold of the magazine. Her love for Hef was so great that she even texted her frenemy, Kim Kardashian, to reminisce about old times. Kim K tweeted about her text convo with her old friend, saying, "Paris & I are reminiscing about the Playboy parties at the mansion & how much we love Hef. She texted me the perfect Hef emojis." It would make sense that Kim and Paris both idolized Hef since they all got their start in similar ways: by masking their lewd indecencies as revolutionary forms of empowerment and expression. Hef was the master at convincing women that they were taking control of their own agency while preying on their insecurities.

19 Creepy Pals

via Renegade Tribune

Hugh Hefner had a lot of friends and it's no surprise that Roman Polanski was one of them. Though he was once known for being a brilliant, up-and-coming European director, he is now known as the criminal who fled the U.S. after having an inappropriate relationship with an under-age girl. In the 60s and 70s, however, Polanski was known as the hip director who made important films like Rosemary's Baby and Chinatown and also for his relationship with Sharon Tate who was also friendly with Hef. Also pictured above is Hugh's ex-girlfriend, Barbi Benton. Considering that Playboy occasionally promoted and endorsed improprieties regarding underage women, the fact that Polanski was a fan is not a shocker.

18 Secret Tunnels?

via Pinterest

There has long been a rumor regarding tunnels that connected the Mansion to various homes around Los Angeles, including the respective homes of Warren Beatty and Jack Nicholson. Considering that the two were notorious womanizers in their day and the fact that they were good friends with Hef, it's not much of a stretch. It's also believed that Kirk Douglas and James Caan had their own tunnels as well. Apparently there is evidence that there were plans and blueprints that featured tunnels connecting the Mansion to various locations but they were (probably) never completed. When asked about the tunnels, Hef, did not confirm or deny that they existed but he did make a joke, saying, "I heard they were closed up sometime in 1989."

17 Yes Men (and Women)

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It's common knowledge, at this point, that Hef loved having women around and the more, the better. It was probably a much easier task to convince women to spend time with him back when he wasn't a saggy old man. In the 70s, he had the typical 70s haircut, flared pants, and he often wore button-down shirts that were always buttoned down too low. What do you expect? It was the 70s! Women wore their hair big and feathered back. According to Madison, Hef only kept people around who did as he said and never opposed him. He created the kind of culture where, in his eyes, he could do no wrong and would gaslight his female companions into believing that everything was their fault and that if they went against him, they were crazy. This sort of manipulation was how he kept so many women around him for so long--that and the money.

16 Hefner's #Goals

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His private jet was nothing if not luxurious--but it was also incredibly trashy. The inside looked like Star Trek meets Barbarella with its futuristic amenities and scantily clad women. Pictured above is Hef with his longtime girlfriend, Barbi Benton, sitting on his round water bed that was covered in a blanket made of opossum fur. He is being handed a drink by one of the Jet Bunnies. What more could the common man want more than a private jet, a beautiful and adoring girlfriend, and a hot stewardess serving them drinks on a waterbed in the clouds? Barbi Benton was born Barbara Benton but Hef insisted that she change her name to Barbi and when they first met, she was 18 and he was 42. She was married to George Gradow in 1979 and they have been together ever since.

15 The King of Pop Loved Bunnies

via Rhythm of the Tide

Michael Jackson had multiple run-ins with Hugh Hefner back in the day, including a night when Tatum O'Neal took him to the Mansion on their first date to watch Roots on VHS. There is also a rumor regarding MJ's costar in his famous Thriller music video, Ola Ray. Apparently, she was cast specifically because she was a Playmate and it intrigued the singer. There is also a rumor, which is probably true, about how Michael would regularly visit the Mansion in the 80s and when LaToya Jackson asked why he was there so frequently, he said, "to see the animals." Hef may have been friends and gotten photos with some of the most famous people in the world but few are cooler than MJ in those stylish shades.

14 Cosby & Hefner: BFFs

via Pinterest

There are few photos that sum up the 70s quite like this photo of Hugh Hefner, Bill Cosby, and some Bunnies watching Shel Silverstein play the guitar at the mansion. Hef was friends with many creeps over the years but few were more devious and disgusting than Bill Cosby who we all know has been under fire recently. According to Hef's ex-girlfriend, Barbi, Cosby was one of the first people she met at the Mansion in 1968. She also said that she thought it was unusual for him to be there so often considering he was a "family man". It turns out that he wasn't exactly the family man everyone thought he was. Still, having a private Shel Silverstein concert is pretty cool.

13 The Famous Mansion

via The Hollywood Reporter

The Mansion first became famous in the 1970s after Hef threw extravagant parties and invited famous celebrities. The mansion is 90 years old and over $15 million has been spent on its renovation and expansion over the years though Hef spent about $1 million on it when he first purchased it in 1971. The mansion has 22 rooms, a wine cellar, an indoor theater, a zoo, a gym, a sauna, and a swimming pool with a waterfall. Over the years, the home has housed hundreds of parties, it has served as a location for various movies and television shows, and it has housed many of Hef's girlfriends. According to Madison, there were events planned at the mansion every night of the week except for Thursdays. On days when there were no events planned, the girls had a 9pm curfew.

12 The Fresh Prince After Dark

via lolsnaps

The Mansion has been featured in a variety of television shows such as Curb Your Enthusiasm, Entourage, Sex and the City, and, of course, The Girls Next Door. Hef also voiced himself in an episode of The Simpsons and as himself in the film Miss March for which he was nominated for a Razzie award. The mansion is also featured in an episode of The Fresh Prince of Bel-Air in which Will and Carlton have the opportunity to go to the mansion because Hilary was asked to pose for the magazine. The most unrealistic part of the episode is when Uncle Phil looks at the magazine and is satisfied with the fact that the photos are actually much more tasteful than he anticipated...at least until he gets the centerfold. In reality, there is nothing tasteful about the magazine but that's Hollywood!

11 The Old Kanye

via celebritypix

Back when Kanye West still wore patriotic baseball caps, Hef and his girlfriend Kendra Wilkinson got a photo with the "Heartless" rapper at the 2008 NBA Finals between the Boston Celtics and the Los Angeles Lakers at Staples Center in Los Angeles. Hef has photos with many famous musicians such as Madonna, Justin Timberlake, Cher, Lil' Kim, Snoop Dog but none of them looked as miserable next to the mogul as Kanye West. Though his future wife was much closer to the bunny creator than he ever was, Kanye still posed for a pic with Hef and his girlfriend. If you look closely at Hef's shirt, you can see that the pattern is magazine covers from over the years. Not very classy but hey, it was 2008.

10 The Girlfriends

via Newsline

Hugh always wanted his girlfriends to look beautiful and also to wear beautiful clothing--the skimpier the better in his opinion. According to Holly Madison, each of the girlfriends were given a weekly allowance of $1,000 to spend on clothing and saving the money or using it to pay off student loans was not allowed. Hef always wanted to be seen with the hottest and most scantily clad women and he spared no expense when it came to his image. Though this photo was taken sometime in the 60s or 70s, the blonde girl smiling right above Hef looks strangely like Holly Madison. As the years went on, his taste in women became more and more refined and soon all of his girlfriends would look shockingly similar.

9 A Man's Fantasy

via Sportsrageous

Men with simple aspirations in life may dream of being surrounded by doting women in lingerie and that is what Playboy offered them and it was what Hefner had for decades. Though this may seem like the ultimate fantasy, if he didn't have the money to give them or the power to make them famous, he would just be an old, wrinkly dude in pajamas. Though Hef said that he never found his "soulmate", it appeared that he was never really looking for one as he always replaced his aging girlfriends with younger models. He definitely wasn't a one-woman type of guy. If you're into women flirting with and fawning over you because of your wealth and power, Hef is the ultimate role model. On a very shallow and basic level, having numerous girlfriends seems like the ultimate goal, at least to shallow and basic men.

8 Fit for a King

via Rolling Stone

Honestly, who doesn't want to sit on a throne on a daily basis? Whatever Hef wanted, he got and if he wanted a wooden throne, he'd get a wooden throne. This photo was taken inside the Mansion which is covered in old furnishings that haven't been updated since the 70s. In 2011, over a 100 people complained of fever and respiratory illness after attending an event at the Mansion and it turns out that there was bacteria building in the mansion that was traced back to the grotto which housed a hot tub. The bacteria they found was Legionella pneumophila and it causes legionnaires' disease. Like most of the glamorous photos taken throughout Hef's life, this one has a very bleak and disgusting background.

7 Say Cheese!

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When Hef first started his magazine, he used a typewriter because that's all there was in the 1950s. This photo was taken sometime in the 1950s or 60s and it features him posing with his typewriter, surrounded models, with a stack of the famous magazine on the table in front of him. It should be noted that none of the women in the photo appear to be happy and most of them look downright miserable. Who could blame them? During the time that this photo was taken, the skimpy clothing worn by the women was seen as much more scandalous than it would be seen as today and they all look very uncomfortable in their getups. The best part of this pic is the man on the right who was apparently only there for the food.

6 Marilyn Monroe's Cover

via The Indian Express

In the first ever issue of Playboy featured its most famous and iconic model: Marilyn Monroe. Before she was famous in Hollywood, she posed in her birthday suit in order to make enough money to keep her car from getting repossessed. Once she began to become a much bigger star, it was revealed that she had posed for the magazine and she was almost excommunicated from Hollywood altogether. However, because the blonde bombshell's regret and shame of being featured in the magazine seemed so genuine, the public eventually forgave her and she became the Marilyn Monroe we know today. Though she helped launch Hefner's career, the two never actually met though he's been exploiting her for years. It was recently announced that he would be laid to rest next to Marilyn Monroe which means that he will continue to exploit her, even in the grave, just by being buried beside her.

5 Hefner's Heyday

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The 70s were the heyday for Hefner and his fortune never reached the heights it reached during that decade. With the eventual invention of the computer and the internet, people didn't need old-fashioned magazines to fulfill their urges and Hefner's worth dropped significantly since the public was introduced to wifi. Since the 70s were all about freedom of expression and free love, the magazine was incredibly successful--even though wasn't as much a freedom of expression as it was the exploitation of women. The pipe-smoking magazine creator lived it up in the 70s with extravagant parties and events at his mansion. In the next few decades, Hef would transition from his bell-bottom jeans and collared shirts to smoking jackets which he pretty much wore exclusively until his death.

4 Roller Skate Disco Party

via W Magazine

Those bell-bottomed jeans were a big trend in the 70s but now they just look ridiculous--not as ridiculous as a grown man roller skating with two girls in bikinis. In 1979, Hef had a primetime special called Playboy's Roller Disco Pajama Party on ABC. In the special, James Caan, Robert Culp, and Bill Cosby all made appearances because they were apparently all BFFs with Hefner. Your first introduction to Hefner may have been in The Girls Next Door but the bunnies creator has a long history with reality TV. In the 60s, he hosted a show called Playboy's Penthouse in the late 50s and early 60s then he hosted the most infamous Playboy After Dark which featured various celebrity guests at the mansion including Sammy Davis Jr., James Brown, Roman Polanski, and Sharon Tate. The show first aired in 1969, the year that Tate was murdered.

3 The Turn of the Century

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As you can see, it took decades for Hefner to establish his very specific tastes for women which is evidently clear by the eerily similar blonde woman above. This photo was taken in February of 2000 and Hef showed no signs of changing his ways after decades of womanizing. He generally had at least three girlfriends at a time and they were all responsible for providing various services in the bedroom though they were allowed to have boyfriends on the side. However, none of the side boyfriends were allowed to come into the mansion though few obeyed this rules. Anytime any of the girls went out, he would take a photo of them and expect them to look exactly the same when they returned because he was obsessed with protecting his image and he required them to all look perfect at all times. How Hugh Hefner ever became portrayed as a champion of female empowerment is a true wonder.

2 Quite the Catch

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Hugh Hefner was just like those basic guys on Tinder who are on a boat, holding up a freshly caught fish in the profile picture. In this photo, Hefner seems to be attempting to create an Ernest Hemingway vibe with the hat and the smoking pipe but he doesn't quite pull it off. This pic was taken in 1970 during a fishing trip in Miami which he took with his girlfriend Barbi Benton. Hefner posted this photo on his official Instagram in 2015 as a throwback Thursday post which is the most basic thing ever. But what can we expect from Hef? To be fair, it was most likely one of his employees who posted the photo because there aren't many men in their 90s who know how to use social media.

1 Blonde Bombshells

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Watching The Girls Next Door may not have seemed very dark back in the mid to late 2000s but as time has passed, the dark underbelly of the legacy has become uncovered. The girls may have seemed like they were living perfect, exciting, and extravagant lifestyles but they were essentially servants to Hefner's whims and desires. According to Madison, he would create drama among the girls by randomly choosing one to be his favorite and let them fight amongst themselves which is a classic form of gaslighting. He would also talk down the women as if they were children which infuriated Madison who had a college degree and he refused to have any conversations about topics such as politics or current events. He liked his women to appear pretty, blond, and dumb.

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