Hugh Hefner died on September 27th, 2017, and his legacy looms large. There’s a lot to talk about when it comes to Hugh Hefner just because of how long he lived in the public eye. He’s the man behind Playboy and ultimately, he’s the man that ended up turning his magazine into an industry. He was also a man who donated lots of time and money to different charitable causes, supported marginalized groups long before anyone else thought to, and had an iconic business with branding that we’d recognize anywhere.
While Hugh Hefner’s achievements will be remembered for decades to come, there’s also a darkness to his life that’s also worth addressing. For all of his contributions to LGBT rights and abortion rights, he was plagued by accusations by multiple women that he’d taken advantage of them. He also would say that he would push for women’s rights while simultaneously calling women objects. Regardless of everything that he’s done, both good and bad, he’s really an interesting person and the world is a different place without him. Here are eight things that Hugh Hefner would want us to remember and eight things he would rather we forget.
16. To Remember: He Was An LGBT Ally Before Many Others Were
Hugh Hefner was an ally to the LGBT community long before it was considered acceptable to be one. He featured transgender woman Caroline “Tula” Cossey in his magazine in 1991, long before the issues of transgender people were recognized on a mainstream, widespread level. Thirty-four years after the issue was published, Playboy would interview Cossey on how she felt about the shoot, and she went out of her way to talk about how accepting and welcoming Hugh Hefner had been to her. “I had done pinups and calendars and glamour shoots, but to be the first transsexual in Playboy, I felt absolutely honored. I remember being invited to the Mansion to meet Hugh Hefner,” she said. “He looked into my eyes and I immediately knew he felt my story. He felt my cause.”
15. To Forget: He Had A Very Specific Standard Of Beauty Set Down By Alice Faye
In an interview with the LA Times, Hugh Hefner went on record as saying that the thing that really defined beauty for him was Alice Faye in the film Flash Gordon. “My taste in women has never really changed. It’s the fantasies I had that came right out of the movies in the 1930s. I think it was Alice Faye and the female lead in the “Flash Gordon” serial who had a big impact on me when I was 10. The only sexy serial ever produced. My buddies and I, on Manly Monday nights — we just finished watching it again.” Alice Faye is beautiful, but he was so fixated on her type of beauty that this is what was set down his magazines for decades. He had many different types of women as Playboy Bunnies, but the ones that he seemed fondest of were his Alice Faye types.
14. To Remember: He Was In The Guinness World Book Of Records For Scrapbooking
Hugh Hefner was in the Guinness World Book of Records back in 2011 for scrapbooking, which is one of those things you might not expect from a guy who’s known for sleeping with lots of women and photographing them for his magazine. His life has been well documented, not just by the media fascinated with him, the women in his life, and the house they all lived in, but by himself thanks to his scrapbooks. It can be estimated that anyone who wanted to do a bio-pic on Hugh Hefner could use his footage and not need to recycle anything for at least a few decades. His scrapbooks go back to when he was a six-month-old baby, and he had a personal archivist whose job it was to keep everything straight.
13. To Forget: He Was Obsessed With Himself
While it’s pretty cool that Hefner was a world-class scrapbooker, it does speak to a certain level of narcissism. Archiving his own life was basically an obsession of his. He has 17,000 hours of personal footage and 2,600 scrapbooks, and Amazon is using these to create American Playboy: The Hugh Hefner Story, mixing documentary footage and biopic. On top of that, some of the weirder stories from the Playboy bunnies have involved him watching play-acted girl on girl action for his own amusement. According to Holly Madison, the girls involved knew that it was basically all fake and for his amusement and would joke around about it while it was happening, but they kept doing it because Hugh Hefner liked the attention.
12. To Remember: He Married Twice And Was Faithful To Both Women
Hugh Hefner actually married the woman who took his virginity after “two years of foreplay.” However, before he and Mildred Williams got married in 1949, she confessed that she’d had an affair while Hefner was in the army. Hefner was a virgin and felt like he’d never live up to his wife’s experience with sex after that. “After that, I always felt in a sense that the other guy was in bed with us, too.” They divorced after ten years of open marriage, and after that, Hefner began his long and storied journey to sleep with as many men as he possibly could. In 1989, he got married again to a woman named Kimberly Conrad. They stayed together for eleven years, and according to both parties, he never cheated on her. They even had two kids together and when the couple divorced, she and their two sons moved in next door.
11. To Forget: His Third Wife Is Getting Nothing
Hefner married once more in 2012 to Crystal Harris, and they stayed married up until his death. She was a former Playmate who actually ran from the altar when the two tried getting married in 2011. The 300-person wedding was called off five days before it happened. According to Crystal: “Last time it turned into a big ordeal and then it all fell apart.” She also admitted that sex with Hefner was really short, she’d only ever done it with him once at that point, and she was over it. The two reconciled later on and Hefner went on record saying that he wanted to stay with Crystal until he died. “The dramatic age difference between Crystal & me really doesn’t matter,” he tweeted. “Whatever time I have left, we want to spend together.” However, he didn’t spend the rest of his life with her without making her sign an ironclad prenup that leaves her with nothing.
10. To Remember: He’s The Reason We Have A Hollywood Sign
We’re so used to seeing a Hollywood sign that we might be unable to imagine that sign not being there. However, in the 1970s, that was very close to being a reality. The sign was in a state of major disrepair, to the point where the locals just wanted to get rid of it. However, Hugh Hefner stepped up and launched a public campaign to save the sign. It worked: he ended up raising about $250,000. He even personally gave the campaign $28,000 to put up a new letter Y on the sign. His care for the sign went beyond this as well. In 2010, he donated one million dollars to help preserve the land around the sign. People don’t really remember Hefner for doing this, but they should since his efforts and campaigning singlehandedly saved the sign.
9. To Forget: Bill Cosby And His Victims At The Mansion
While we don’t know how much of this is unsubstantiated fact, we do know that Hugh Hefner was added to a civil lawsuit against Bill Cosby for sexual battery, gender violence and other charges stemming from a 2008 incident that occurred at the Playboy Mansion. According to Chloe Goins, Bill Cosby plied her with drinks and quaaludes and “molested” her while she was unconscious. Hefner denied that he knew Cosby was drugging women at his house and even went so far as to say that he would never tolerate anything like that, even if they were a friend. However, Holly Madison’s memoir detailed an incident where Hefner referred to quaaludes as “thigh openers,” so there’s no way to know what’s actually the case here.
8. To Remember: He Started The Magazine Because Esquire Wouldn’t Give Him A Raise
Hugh Hefner was in the army during the 1940s, and afterward, he attended the University of Illinois at Urbana Champaign. He earned degrees in psychology, creative writing, and art there. That allowed him to get a job working at Esquire as a cartoonist. However, when he asked for a five dollar raise and was rejected, he left Esquire with a dream of starting his own magazine. Within a short period of time, he got fifty investors together, raised $8,000, and jumpstarted Playboy into existence in 1953. One of the investors was his mom, who put her own money into the project despite being a conservative person who wouldn’t have wanted Playboy to be a thing. She did it not because she believed in the project, but because she believed in her son.
7. To Forget: The Bunnies Living With Him Had To Obey Strict Rules And Deal With Bad Living Conditions
We’re so used to thinking of the Playboy Mansion as insanely magnificent, but reports from Playmates in the later days of the Playboy empire painted a totally different picture. Former Playmates like Izabella St. James, who lived in the mansion for two years, have come forward with their stories. St. James, for example, told a sad story about a house that was stuck in the past and was actually kind of gross.
For two years, she lived in a mansion that had old mattresses, stained carpets, and a ton of rules. For one thing, they had to conduct themselves a certain way on social media, and they had a curfew of 9 PM. Carla Howe said of the place: “He almost never leaves home and refuses to change anything in the mansion, so the whole place feels like it’s stuck in the 1980s. There is no velvet or gold and all the carpets are brown and curling.”
6. To Remember: The First Cover Was A Five Year Old Photo Of Marilyn Monroe
Once the money to get Playboy off the ground was raised, Hefner needed a cover photo. So he looked through the files of a calendar company based out of Chicago, which is where he found a photo of Marilyn Monroe that was about five years old. He bought the photo for $500 and put it on his cover. When the first issue came out, it sold over 50,000 copies. There have been a ton of famous Playboy covers over the years. Some of the most famous ones include Katie Price topless, the famous Baywatch cover, Kate Moss in the bunny outfit for the 60th-anniversary issue, the strange Christmas cover with Naomi Campbell, and more. There’s also the five covers Anna Nicole Smith did, especially the one with the headline “$450,000,000 Playmate,” and the issue that came out memorializing her death in 2007.
5. To Forget: The Mansion Eventually Became Stained With Dog Poop
The disrepair of the mansion went even further than messed up carpets and perpetual 80s decor. According to the girls who spoke out about the conditions at the mansion, the only time the place ever looks good is when it’s decorated for parties and the zoo animals are everywhere. Unfortunately, according to Carla Howe, even the zoo is a thing of the past. “But even the animals are getting old. One of the monkeys recently died aged 100.” On top of that, the whole place was stained with piles of dog poop from Archie, the house dog, at the time Izabella St. James was there. “Every Friday morning we had to go to Hef’s room and wait while he picked up all the dog poo off the carpet,” she said. “We then asked for our allowance — a thousand dollars counted out in crisp hundred-dollar bills from a safe in one of his bookcases.” To make matters worse, over 100 people caught Legionnaires disease in the swimming pool back in 2011.
4. To Remember: Dick Gregory Wouldn’t Be Famous Without Hef
Dick Gregory, the legendary comic, probably wouldn’t be as big as he is without Hugh Hefner. Gregory was performing at the Herman Roberts Show Bar in Chicago back in 1961 and Hefner happened to be there. That was when Hefner invited him to work at his Playboy club in Chicago, which was what got Dick Gregory to the next level. Hefner also hired Bill Cosby to work at his club which did a lot for his career as well. This is a pretty big deal because this was happening in the sixties when segregation was still a big deal in America. Hugh Hefner looked past segregation and just saw the talent of his comics, which is a pretty admirable thing in any decade.
3. To Forget: Holly Madison’s Accusations
Holly Madison, the favorite Playmate girlfriend at the time of the EW reality show The Girls Next Door, write a memoir about her life in the mansion. She’d dreamed her whole life of becoming a Playmate, only to get there and find that it was not all it was cracked up to be. According to Madison, she was never actually given the chance to consent to sex with Hefner, it was just expected once she moved into the mansion. “I think everybody just assumed because I was there and making it clear that I wanted to be a girlfriend that I knew something went on,” Madison said. “And I knew something went on. I’m not stupid. But none of the girls would ever really admit to it or talk about it.”
She was part of the staged “group” sessions which she wasn’t all that comfortable with. Hefner would allegedly also be very critical of her looks and eventually forced her to quit her job at Hooters, which was one of the things that let her feel independent. Once she was cut off from the rest of the world, she became really depressed and contemplated suicide. Even then, Hefner wouldn’t let her see a therapist, so she had to get antidepressants from a regular doctor. “Drowning myself seemed like a logical way to escape the ridiculous life I was leading. I just couldn’t take my misery anymore.”
2. To Remember: Two Of His Clubs Refused To Hire Black Women So He Bought Them Out
Back in the 1960s, Playboy clubs were everywhere, which was great for business and great for Hefner. However, he wasn’t happy with everything. He found out that two of his clubs in New Orleans and Miami were going out of their way to not hire black women as Playboy bunnies and making sure African Americans couldn’t be members of the club. He bought those two clubs himself at a financial loss, then made it clear that he wouldn’t ever tolerate that kind of behavior at one of his clubs. “We believe in the acceptance of all persons in all aspects of life on the basis of individual merit and without any regard to race, color, or religion,” he wrote in a memo after making the purchases. It just goes to show that Hugh Hefner really cared about his business, but he cared more about treating people like people.
1. To Forget: He Outright Called Women Objects And Promoted Toxic Masculinity
Hefner talked a big game about women’s empowerment, but he didn’t walk the walk. He would always say that he supported women and wanted them to feel empowered, but that didn’t translate to how he treated the women in his life. Take Holly Madison, who had to quit her job that she liked and made her feel independent because he made her.
When Vanity Fair’s John Heilpern brought up how Hefner makes feminists mad for treating women like sexually available objects, his response was “They are objects!” Even when he denied Madison’s claims, he still made it a point to talk about all the women he’s dated, while skimming over the importance of allowing women to lead independent lives, which the women in the mansion didn’t really get to do.
While Hugh Hefner accomplished a great many things and spoke out against a lot of injustice, there’s a lot he wouldn’t want us to remember about him. Regardless, we should remember those things about him because the bad things are as much a part of a person’s legacy as the good things.
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