What Hugh Hefner's Ladies Don't Want You To Know About The Legend

We thought our list of little-known facts about Hefner would be the perfect way to remember him. RIP.

With Hugh Hefner dying from natural causes at the Playboy Mansion, the world has lost yet another magazine editor. And those guys are gold. But he wasn’t just an editor; nor was he just a millionaire or even just a guy surrounded by 'beautimus' twinkies.

Hefner was a political campaigner and philanthropist, and with the first edition of the Playboy magazine in 1953, he singlehandedly fashioned a new movement in self-expression. At a time when the world was full of magazines concerned with fishing and cars, Playboy broke a mold. Its success was also down to the willingness of celebrities of the moment to pose -- women such as Jayne Mansfield, Pamela Anderson, and even Madonna.

The magazine went into decline in the 1980s and found itself on the business end of new laws governing nightclubs and explicit sexual images. But recently, Hefner - with the help of his son Cooper - had steered the Playboy brand to new ventures and gave the magazine a more mainstream image.

Hefner was 91 at the time of his death and yet maintained a playboy image to the very end. The pajama-wearing entrepreneur famous for living a life full of riches and sex was still reportedly dating Playboy models in recent years and hosting lavish parties at his luxurious mansion in Los Angeles. In 2012, as if to prove a point, he married Crystal Harris, who was 60 years younger than him.

We thought our list of little-known facts about Hefner would be the perfect way to remember him. RIP.

15 “Easily More Than 2,000”

Hefner has always said that he was faithful in every marriage but “made up for it” during periods of being single. It was in these times that Hefner cemented his image as the playboy with an avid sexual appetite. Having the Playboy Mansion helped. The women to whom Hefner had given modeling contracts were offered board at his Los Angeles home, which meant a ready supply of hot pocket.

When asked by the Mail Online in 2004 how many women he had slept with, he remarked that he had lost count but that it was “easily more than 2,000.” “There were chunks of my life when I was married,” he said. “And when I was married, I never cheated. But I made up for it when I wasn't married. You have to keep your hand in.” Hefner’s “discovery” of Viagra was said to have been a big help.

14 Testing The Boundaries Of Gayness

Hefner may have had the reputation of a womanizer and a man living with sex on tap but his amorous intentions have not always been straight. According to those who knew him during the 1980s, Hefner became interested in “testing the boundaries of his sexual appetite” (The Sun, 2017). In so doing, he added one or two gay men to his list of conquests.

According to the Washington Post, Hefner engaged in sexual activity with men during his swinging days. “There was some bisexuality in the heterosexual, swinging part of my life,” Hefner told the Post in 1999. “I was testing the boundaries, just knocking down walls. But that period of sexual experimentation is long gone.” His ex-girlfriend Carrie Lewis seconded his admission after the pair split in the 1980s. It may come as a surprise to some of us who believed Hefner was adequately sated by women.

13 S-x Is Bad For Your Hearing

It’s commonly agreed that Viagra is good for one thing only. The pills arrived on the market in 1998 and are given in a dosage that’s right for the patient. Hefner seemed not to worry about dosages. The four hours of normal function the user enjoys can’t have been long enough because he regularly overdosed. The Independent in 2017 claimed that Hefner was “notorious for popping Viagra like Skittles in order to maintain his very active sex life.”

But one of the side-effects of taking too much Viagra is hearing loss. The drug has been linked to sudden sensorineural hearing loss, which, if not medically dealt with, can lead to permanent damage. It's little wonder then that in 2011, the head of the Playboy Mansion had “gone deaf from taking too much Viagra,” according to two of his former lovers Karissa and Kristina Shannon (The Sun, 2011).

12 NORML Money

It was thanks to Hugh Hefner’s contributions to NORML (the National Organization for the Reform of Marijuana Laws) that the organization was able to maintain a presence after its 1970 inception. Begun by Keith Stroup, NORML – which aims to legalize, “the responsible use of marijuana by adults” (NORML, 2017) – found little support amid communities and was failing to tempt investors. Stroup recalls how he was surprised at Hefner’s keen interest.

“Hefner had been someone who used to be an alcohol drinker,” Stroup told magazine Leafly. “But he had given up alcohol some time ago and had become a marijuana smoker. So he had a personal interest in the issue, [and] understood that it should be legal” (Leafly, 2017). As the organization grew, Hefner was donating around $100,000 a year and became its top financier. Without his help, NORML would almost certainly have folded.

11 Famous Cousins

In 2004, Hugh Hefner revealed to CBS news he was related to William Bradford. Bradford was the leader of the very first English commune that was set up after its community’s voyage on the Mayflower. “I'm an 11th generation direct descendant of William Bradford,” he said. “A direct descendant of a puritan.” That might be seen by some as the pinnacle of irony especially when Nerve Magazine tells us Hefner would “achieve intimacy with around eleven of every twelve Playmates of the Month in any given year.”

But you may not know that Hefner also had some famous living cousins, namely George ‘Dubya’ Bush and Senator John Kerry. Kerry served as the 68th United States Secretary of State under the direction of former president Barak Obama. Although Hugh Hefner is more closely linked to Bush - being his 9th cousin twice removed – he told CBS News that he felt “closer to Senator Kerry.”

10 Four Minus Two Equals Just As Much Fun

Mildred Williams was Hefner’s childhood sweetheart, and they were married in 1949. After finding out that she had had an affair, Hefner was devastated. In an effort to reconcile her new marriage, Mildred allowed Hefner to sleep with other women and, in so doing, gave rise to his womanizing reputation. In that way, she lessened her guilt as well as balanced the infidelity, but notwithstanding her efforts, the pair was divorced in 1959.

While they were married, Hefner had arranged for Mildred to engage in a foursome with Hefner’s younger brother Keith and Keith’s wife, Rae. In his book “Mr. Playboy: Hugh Hefner and the American Dream,” Steven Watts writes, “Hef then went further, trying a foursome out on his own family. It did happen with his brother, Keith, and his wife, Rae, one evening. [But] while Millie ultimately backed out of having sex with Keith, Hugh slept with his sister-in-law” (Huffington Post, 2008).

9 Playboy Comforter

The Bunny logo, which is instantly recognizable as the Playboy brand, has been used since the second edition of the magazine. It was designed by an art specialist called Art Paul who, it's believed, modeled the logo after talking to Hefner about a childhood comfort blanket. The blanket sported the image of a rabbit, and it seemed logical to Hefner that it should be used as a way to define a brand that published images of beautiful women.

On why a rabbit was finally chosen as the magazine’s logo, Hugh Hefner told LogoMyWay, “The rabbit, the bunny, in America has a sexual meaning; and I chose it because it’s a fresh animal, shy, vivacious, jumping – sexy. First, it smells you, then it escapes, then it comes back, and you feel like caressing it, playing with it. A girl resembles a bunny. Joyful, joking” (LogoMyWay, 2016).

8 Marilyn Monroe Pictures

The Washington Post this year claimed that actress and model Marilyn Monroe “helped turn [Hefner] into a publishing mogul and cultural force.” And it cannot be denied that the cult status she enjoyed at the time would have enticed the American man to buy a copy of the magazine. She appeared on the front of the first issue, and the caption on the cover read, “First time in any magazine, FULL COLOR, the famous MARILYN MONROE NUDE.”

The two never met, but Hefner bought a nude photo of her for a reported $50 from a Chicago calendar company calling her the “Sweetheart of the Month” (later known as a Playmate). It was also rumored that Monroe hadn’t given her permission for the picture to be used. Nevertheless, in 1992, Hefner purchased the crypt beside Monroe in Westwood Village Memorial Park Cemetery. “Spending eternity next to Marilyn is too sweet to pass up,” he told the Los Angeles Times.

7 Cut Crystal

Hefner married Crystal Harris at a ceremony on New Year’s Eve in 2012. The 26-year-old model was asked by a reporter for Huffington Post what cause she had to marry someone 60 years older, and she replied, “More security.” Whether this was before or after the wedding is unclear, and while her marriage to the living Hefner offered some guarantee, the dead Hefner is in no way ready to share his fortune.

In 2017, the Mail Online reported that “before the nuptials, Harris was said to have signed an 'ironclad' prenuptial agreement. A source told US Weekly that while the blonde beauty will be taken care of, she won't receive a penny of his fortune.” And it's a substantial fortune. In spite of his losses, Hefner’s estate is estimated to be worth in the region of $43 million – all of which will now be divided equally between his four children.

6 Prison Break

The Playboy Mansion was sold in 2016 for $100 million. Since 1971, it had been the home of Hefner, his wives, and his Bunnies. It was seen by the media as the epicenter of a hedonistic empire, to which only elite celebrities were invited. Lavish parties and publicity stunts were held on its grounds, but its true scale was kept a secret. According to The Sun, as of 2017, the property comprises “a wine cellar, three zoo buildings, a game house, tennis and basketball courts, a waterfall, pool, and the famous grotto where Hefner would entertain.”

But in recent years, the house has been criticised for being dirty, squalid, and tired. The Mansion has the feel of a prison, with squalid and grubby living conditions and a 9 PM curfew for the resident bunnies, according to British newspaper The Mirror. It was sold with the proviso that Hefner could live there until he died.

5 Vanna White Pictures Leave A Bad Taste

Wheel of Fortune star Vanna White modeled lingerie in 1987 in an effort to make some extra money. “What happened was, when I moved to Hollywood, I was too embarrassed to ask my dad for money for rent," the 58-year-old told an AOL reporter in 2016. “I did some lingerie shots, like we all do sometimes... back in those days, and Hugh Hefner bought the pictures.” What she didn’t realize at the time was that Hefner had bought the images with the intention of including them in an issue of Playboy.

“Hugh was my friend, and he said, 'Vanna, we are going to put you on the cover.' I said, 'If you put me on the cover, my career could be ruined.'” The pictures were printed with no regard for White’s fears, but the shots didn't ruin her career. By that point, she was already five years in as the host of Wheel of Fortune and has been ever since.

4 Legionnaire Found In Mansion

Although famed for his exuberant parties, Hefner’s housekeeping (or lack thereof) left guests feeling a little hot under the collar. At a conference for internet investors in 2011, 69 people fell sick at the event, followed by a further 123 afterward. They all exhibited a fever, headache, cough, shortness of breath, and aches, and three of them tested positive for H1N1 flu, a strain of Legionnaire’s disease.

An investigation of the hot tub at the Mansion revealed that the legionella bacterium was present in the water. The bacterium grows best in warm water, and the disease is contracted by breathing in small droplets. The Los Angeles health department visited the Mansion the day after the event and took away samples of the water for analysis. It later identified the bacterium but issued a statement that its findings were inconclusive in reference to the outbreak of illness.

3 Bill Cosby

The recent declaration of a mistrial in the case of Bill Cosby vs. Andrea Constand hasn't thwarted the plans of Los Angeles Superior Court Judge Craig Kaplan. Scheduled for July 30, 2018, a case is to be brought against Cosby for sexual molestation of a 15-year-old girl at the Mansion in 1974. The claimant, Judy Huth, was 15 at the time she alleges the crime took place and is just one of many other such victims.

Hefner invited Cosby to the Mansion for a party. Huth claims Cosby invited her and a friend to accompany him to Holmby Hills and that, at some point during the party, Cosby sexually assaulted her. She alleges he “proceeded to sexually molest her by attempting to put his hand down her pants, and then taking her hand in his hand and performing a sex act on himself without her consent.”

2 Cardboard Cutout

The famous cardboard cutout was to be found in the ornate dining room next to the dining table at which Hugh Hefner never sat. Prior to the Bunnies being moved to a house nearby in 2002, dinner was a strict affair, with everyone expected to be in attendance. However, according to Esquire Magazine in 2017, “The industrial kitchen and its venerable staff will prepare just about any American meal a man could want.”

And the point of the cardboard cutout? Because Hefner hardly ever joined in socially with the residents and guests, it was a reminder of his presence: life-sized, smiling, and wearing black silk pajamas. After all, it was more or less by grace and favor that anyone stayed at the house. Judging by the rumors that emerged in the last decade of Hefner’s failing libido, we suspect there was more life to the cardboard cutout. But let's not speak ill of the dead.

1 Having The Kids Over

Hefner sired four children: Cooper, Christie, Marston, and David. According to Holly Madison’s new book, “Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny,” Hefner made two of his children stay over in one of his girlfriend’s rooms. “He made his sons Marston, 9 years old, and Cooper, 10, share a bedroom with a girlfriend,” she writes. “Though they never stayed over when I was there, there were still toys scattered across the bedroom floor, which made for an incredibly odd, and frankly, creepy juxtaposition."

Before Christie arrived at the Mansion, Hefner would clear the house of evidence of his activities with women in order "to keep the realities from his own daughter” (Christianity Today, 2017). But in truth, the property, with its “Grotto, a zoo full of exotic animals, and private forest of redwood trees” (Business Insider, 2016), allowed the children an opportunity to just adventure and marvel.


Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

What Hugh Hefner's Ladies Don't Want You To Know About The Legend