People say we cannot separate who we are from what we do. If that is the case, no one could do a better job of portraying the adage than Hugh Hefner, the Playboy.

Once a copywriter for Esquire, he left the job after being denied a $5 raise and started his own publishing company, Playboy Magazine.

Hefner also was the editor-in-chief for his magazine pretty much his entire adulthood and lived a life that couldn’t be more reflective of what he published until his time of death on September 27, 2017, at the age of 91.

TIME once described Hefner as a prophet of pop hedonism, Vanity Fair regarded him as an iconic playboy, and The Washington Post called him a visionary editor.

Those who adored him would love to remember the man as an “Enlightened Publisher” and “The Godfather of the S*xual Revolution,” yet many saw him as just a dirty older man.

For sure, Hugh Hefner was many things; perhaps too many you probably didn’t know that underneath his red smoking jacket were some shocking oddities.

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10 It Started With A S*xual Rejection

At his younger age, during high school in his hometown of Chicago, Hefner was once rejected by a girl. Now, this might sound like nothing unusual for any young man to experience, but he took the rejection with an oddity of a peculiar kind.

Soon after the crushing moment, he preferred to be called “Hef” instead of “Hugh.” He started drawing a comic strip about himself’s fantasy version, which eventually manifested as a reality in his adult life.

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9 A Crush On Alice Faye

In a 2009 interview with Los Angeles Times, Hefner said that his taste in women has never changed. One of his first fantasies came right out of movies in the 1930s, specifically Alice Faye and the female lead (most likely Jean Rogers) in the “Flash Gordon” serial. Both women had a significant impact on Hefner when he was 10.

 He even went as far as saying that it was the only s*xy serial ever produced. As it turned out, he always saw the female actors as beauty ideals – blonde and big breasted – highlighted through his enterprises.



8 Hef Wasn't Always The Playboy He Ultimately Became

Throughout his life, Hefner married three times and had s*x with probably a few thousand women. In 1949 when abstinence before marriage was not unusual, he married the first girl with which he had s*x. It was Mildred Williams.

 He managed to “save” himself until the relationship was formalized, but it did not turn out well. While the two were engaged, Williams confessed to an affair, conducted when Hefner had been in the army.

They divorced ten years later, followed by Hefner remaking himself yet again, working on the thousands of s*x partners throughout life.

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7 Catching Disease In The Swimming Pool

For many people, Hugh Hefner lived like a Bachelor King in the famous Playboy Mansion. It wasn’t always like that.

In January 2016, Playboy Enterprises sold the mansion for a whopping $100 million to a private equity investor Daren Metropoulos because the company was getting deeper under mounting debt.

 At that time, the building had already lost its former glory, and the money was mostly tied-up to its historical legacy. In fact, in April 2011, more than 120 guests caught Legionnaires’ disease during a fundraising event, a severe form of pneumonia caused by bacteria in the mansion’s swimming pool.

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6 Two-Second S*x

Holly Madison was once Hugh Hefner’s number-one girlfriend. She moved in at the Playboy Mansion in the early 2000s at the age of 21, while Hef was 74 years old.

In her tell-all memoir released in 2015, Madison claimed she couldn’t even recall what s*x with Hef felt like beyond having a heavy body on top of her.

Hefner’s final wife, Crystal Harris, even said that she only had one instance of s*x with her late husband; she claimed it lasted for just about two seconds.

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5 Orgy Bedtime Ritual

In another part of Madison’s story, “girlfriends” needed to take part in Hefner’s bedtime ritual, involving a “group orgy” in which King Hugh would be the focus of their pleasure-inducing activities. He multitasked in the ceremony as he also smoked pot and watched p*rn somewhere along the way.

 Every girl would get her turn, albeit very briefly before Hef moved to his actual girlfriends and finished himself off. In fact, according to Madison, he always finished himself off.

4 His Bedroom In One Big Mess

On the media, Hefner always pictured himself as a real womanizer who could wreak havoc in the bedroom with as many girls as he wanted.

From Madison’s memoir, we have a clue that he was not as manly as he would like you to think, but still, the story doesn’t cover Hefner’s competence in his heyday; maybe he indeed had been mighty before old age got to him.

As Hefner grew old, however, he did wreak havoc in his Playboy Mansion bedroom literally. It was messy and full of litter that meant nothing to no one but him.

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3 Hef Would Pay For Any Plastic Surgery His Girlfriends Wanted

If any of his girlfriends had found the need for plastic surgery, Hef would pay for it. Any plastic surgery was allowed.

He also had an open account at a beauty salon in Beverly Hills where his girlfriends could ask for any treatment at any time. Blonde hair dying, nose job, breast augmentation was nothing out of the ordinary.

 In addition to providing free beauty treatment, every single girlfriend took a $1,000 a week allowance received every Friday morning. He also used the occasion as a place to speak up about his complaints about anything.

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2 Old Man Who Enforced Curfew

On any given day, it is safe to assume that many things, good and bad, happened inside Playboy Mansion when Hefner was alive. There could be parties where guests took drugs and s*xual acts in every corner, and Hef wouldn’t mind at all.

He didn’t want to happen because any of his girls wander around, especially outside above 9 pm. All his girlfriends had to be in the mansion and ready for bedtime ritual with a specific dress code unless they were out somewhere with the man.

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1 Plenty Of Personal Notes

Hugh Hefner was in the Guinness Book of Records for having the most extensive collection of personal scrapbooks. The number is believed to be more than 2,600 in addition to 17,000 hours of private footage.

It is a vast record that went back to when he was just a six-month-old baby. A personal archivist in his payroll would clip, note, and record everything that happened to him.

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