Disturbing Things Everyone Just Ignores About Hugh Hefner

Hugh Hefner, who died Sept. 27, 2017, at age 91, considered himself the leader of a sexual revolution. In 1953, he pioneered Playboy magazine, creating a multi-million dollar multimedia brand. Though there's nothing revolutionary about objectifying women, Hefner did keep feminists in business and make a fortune behaving very badly through the years. He also became wildly revered around the world. After his death, CNN called him "a cultural icon" who "championed a more libertine view of sexuality that went against the puritanical elements of the times" and turned his brand "into a forum for sexual freedom and progressive politics, advocating for civil rights and free speech." 

There's no doubt, "Hef" made his mark, but not without a whole lot of controversy, too. From his sketchy business dealings to his many girlfriends and those legendary parties, brace yourself because when it comes to Hefner's dirtiest decisions, we're about to bare it all.

He ripped off Marilyn Monroe

One of Hefner's earliest dirt-bag moves was screwing over sexy sweetheart Marilyn Monroe. In 1953, the Gentlemen Prefer Blondes star became Playboy magazine's first "playmate of the month." For Monroe, this was not the honor Hefner chalks it up to be. Reportedly without her permission, he acquired and printed a photo from a nude calendar the actress had posed for in the past. Monroe was paid $50 at the original photo shoot. Hef paid the calendar makers $500 for the rights. According to Highsnobiety, that debut issue of Playboy sold between 50,000 and 65,000 copies (at 50 cents a pop). Those were huge numbers at the time, so Monroe essentially put Hef on the map and lined his pockets. Monroe and Hefner never even met. "She was gone, sadly, before I came out [to California]," he told the Times of India.

Here's another uncomfortable factoid: Hefner supposedly adored Monroe so much that he decided to encroach upon her peaceful rest for all eternity. The Guardian reported that Hefner purchased the mausoleum right smack dab next to hers at the Westwood Village Memorial Park Cemetery in Los Angeles for $75,000 in 1992.

He exploited Marge Simpson

In 2009, Hefner posted a tweet that set the water cooler to boiling: "Marge Simpson has a surprise for her fans in the November issue of Playboy." 

That's right, the magazine decided to put its first objectified cartoon on the cover in hopes of attracting younger audiences and combating diminishing circulation. "The shock value always does Playboy very good," Media Industry Newsletter online editor-in-chief Steve Cohn told CNN. "This is a novelty one, but it's no different than a celebrity. In a sense, Marge has something in common with a woman who's never done it before, someone like Nancy Sinatra."

"Marge Simpson is the quintessential girl next door who stole our hearts 20 years ago and has held them captive ever since," Hefner told CNN. "We were delighted to learn she wanted to grace the pages of our magazine. Her pictorial is truly stunning." Do you think Hef asked Simpson for her blessing first?

He took advantage of Vanna White

One of the 1987 Playboy cover girls was Wheel of Fortune's one and only Vanna White. Based on her squeaky clean image on the game show, this may sound implausible, but don't put anything past Hugh Hefner. Like Marilyn Monroe, a young and cash-strapped White had done a lingerie shoot to make ends meet, and Hefner later bought those images.

"I wasn't on [the cover] because I wanted to be," White told The Wendy Williams Show. She even asked Hefner, who she considered a friend at the time, to refrain from publishing those pictures from her past. "I said, 'Hef, if you put me on the cover, my career could be ruined...' They did it anyway." 

Fortunately, that spread did not undermine White's career. She has starred on the iconic game show alongside host Pat Sajak for more than 35 years. The did, however, put the kibosh on her friendship with Hefner.

He bribed Holly Madison

Holly Madison reigned supreme as one of Hefner's live-in girlfriends from 2001 until 2009, when she decided to ditch her bunny ears and cotton-ball tail. In 2015, she released a tell-all memoir titled Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. In the best-seller, she claimed Hefner attempted to bribe her to remain at the Playboy Mansion by intentionally leaving his will out for her to see. According to Page Six, Heff planned to bequeath her $3 million if she stayed. Bribing a lady to stay at your house is pretty lame, right?

How did Madison react? "It just kind of disgusted me more than anything because all he can do is say, 'Oh, here, I'm gonna throw you some money to get you to stay.' It just grossed me out," she told Oprah Winfrey's Where Are They Now? program.

The Playboy grotto made people sick

This infamous oasis at the Playboy Mansion has been the location of many a star-studded event, but apparently, the Playboy grotto is dirty in more ways than one. 

After a DomainFest fundraiser in 2011, many attendees fell seriously ill. According to the Los Angeles Times, health authorities said the bacteria legionella pneumophila (commonly known as Legionnaires' disease) were identified at a whirlpool spa at the bunny den. According to a survey issued by health investigators, "123 people fell sick with fever and at least one other symptom, such as headache, cough, shortness of breath or aches. A key clue was that 69 people got sick on the same day, Feb. 5. That indicated that the outbreak was probably caused by a single source." 

A Playboy spokeswoman declined to comment on that story. 

The Girls Next Door was an unpaid gig

The Girls Next Door reality show, starring Hugh Hefner and his live-in girlfriends, debuted on E! in 2005. While the show's biggest draws were playmates Holly Madison, Kendra Wilkinson, and Bridget Marquardt, the roommates were reportedly not paid for participating on the hit show. 

According to GQ  magazine review of Madison's book, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Wilkinson once asked a producer for compensation. His alleged response? "You. Are. Replaceable...This is not a show about the girls, it's about Hugh Hefner." 

To be fair, Wilkinson spoke lovingly about Hefner after his death, telling People in a statement. "Hef changed my life ... I couldn't be more thankful for our friendship and our time together. I will miss him so much but he will be in my heart forever." Wilkinson was also able to spin-off her Playboy fame into a highly lucrative reality TV career of her own.

But in case you were wondering how Hef keeps the rest of his bunnies underfoot, apparently that's how.

The allowance ritual

The girls may not have received compensation for their reality television appearances, but they were paid to live in the mansion: $1,000 weekly and all the plastic surgery they wanted. However, this weekly grand was not direct deposited into their bank accounts. 

According to former Playmate Izabella St. James, who wrote Bunny Tales: Behind Closed Doors at the Playboy Mansion (via Cosmopolitan), "Every Friday morning we had to go to Hef's room, wait while he picked up all the dog poo off the carpet—and then ask for our allowance: a thousand dollars counted out in crisp hundred-dollar bills from a safe in one of his bookcases. We all hated this process. Hef would always use the occasion to bring up anything he wasn't happy about in the relationship. Most of the complaints were about the lack of harmony among the girlfriends—or your lack of sexual participation in the 'parties' he held in his bedroom. If we'd been out of town for any reason and missed one of the official 'going out' nights [when Hefner liked to parade his girls at nightclubs] he wouldn't want to give us the allowance. He used it as a weapon."

He buddied up with Bill Cosby

A woman who claims Bill Cosby sexually assaulted her at the Playboy Mansion in 2008 added Hugh Hefner to her lawsuit, claiming the Playboy kingpin knew about Cosby's alleged predatory behavior but did nothing to protect her, reported TMZ in May 2016. According to the victim, it was Hefner who introduced her to Cosby. The suit alleges Hefner had a habit of inviting "young and impressionable and possibly minor children to his residence and providing alcoholic beverages." 

According to Business Insider, Cosby was a frequent flyer at the mansion. Another woman reportedly claimed Cosby sexually assaulted her there in 1974 when she was 15-years-old.

Hefner issued a statement in 2014 that seems to simultaneously support and oppose the comedian. "Bill Cosby has been a good friend for many years and the mere thought of these allegations is truly saddening. I would never tolerate this kind of behavior, regardless of who was involved," Hefner said.