Pornographers aren’t exactly held up as models of morality, but for as long as most of you have been alive, society has regarded Hugh Hefner as its horny but harmless grandpa. He wore that silly robe, frolicked in his mansion for the reality TV cameras, and generally didn’t seem to be hurting anything except maybe the souls of interior decorators everywhere. How wrong we were.

He Pressured His Girlfriends Into Plastic Surgery (To Look the Same)

Hefner with girlfriends

(Luke Ford/Wikimedia Commons)

Hefner was famous for his harem of girlfriends who looked like they were stamped out in factory molds, and that’s truer than you probably think. His girlfriends say they were encouraged to plastic surgery themselves into his blond-haired, big-boobed, bland-faced ideal for the same reason cult members have uniforms. When one of them, Holly Madison, tried to express a grain of individuality by cutting her hair, she says he “flipped out.”

He Financially Controlled Them

Hefner’s girlfriends say they weren’t allowed to work outside of the mansion. Instead, they were paid $1,000 a week, but he threatened to dock their “pay” if they did something he didn’t like, which could be anything from going out of town to not screwing a septuagenarian as enthusiastically as expected.

He Refused to Use Condoms or Do Anything to Prevent STDs


(Reproductive Health Supplies Coalition/Unsplash)

Ex-girlfriend Izabella St. James says there was a hierarchy in Hefner’s harem, and one of the “perks” of being the number-one girl was kicking off the relay race that was sex with Hefner, which wasn’t so much enjoyable as “safest for her” because Hefner refused to use condoms. He also refused to get tested for STDs on a regular basis even though they were known to run rampant through the mansion. Two models who said they contracted chlamydia there in the late 2000s were reportedly brushed off by Hefner’s assistant, who told them that was just “normal when you’re sexually active.”

He Had Other Ways of Preventing Pregnancy

Multiple Playboy employees have claimed that Hefner and his friends were more concerned with the risk of pregnancy -- not enough to, you know, use condoms, but enough to pressure the more disposable women in their grasp into acts that carried a lower risk of inconvenient babies. We’re talkin’ ‘bout butt stuff, folks.

Bunnies Say They Were Drug Mules


(Christina Victoria Craft/Unsplash)

By all accounts, drugs flowed as freely through the mansion as STDs, Quaaludes (which Hefner called “leg spreaders” and “thigh openers”) for the women and cocaine for everyone. Various ex-Bunnies have claimed that Hefner got prescriptions in all his girlfriends’ names and sent them out to meet with cartel members, apparently too busy brushing his robes or whatever to do his own dirty work.

His “Cleanup Crews”

Multiple former Playboy employees have spoken of the “cleanup crews” employed by Hefner to do a lot more than mop the sticky, sticky floors. It was their job to cover up anything that might bring Playboy bad press, from deaths to sexual assaults. One employee claimed that between 40 and 50 women who had been sexually assaulted at the mansion or one of the company’s clubs (including some allegedly by Bill Cosby, who was “one of Hefner’s best friends”) were silenced by Playboy.

He Was Accused of Assault Himself

Multiple women have accused Hefner of sexually assault, including one ex-girlfriend who claimed he had a key to every bedroom in the mansion that he used to “surprise” sleeping women. Director Peter Bogdanovich claimed in his biography of Playmate Dorothy Stratten that Hefner raped her when he thought she slept with one of his friends before him (an incident Hefner’s valet claimed to have witnessed), and while Hefner’s lawyers pressured the book’s publishers to remove the word “rape,” they were apparently fine with “forced ‘seductions.’”

He Was Obsessed With the Manson Family

Charles Manson

(California Department of Corrections and Rehabilitation/Wikimedia Commons)

Several people revealed to director Alexandra Dean during the filming of Secrets of Playboy that Hefner was obsessed with the Manson family and even owned home movies they made at their Ranch O’ Murder. This is especially creepy because he was friends with Sharon Tate, but one ex-girlfriend explained that he admired the way Manson controlled women and studied his methods.

He Tried to Silence Feminist Critics

Woman with tape over her mouth


In 1970, Hefner ordered his staff to produce a “hit piece” on the feminist activists who had -- not without cause, it turns out -- criticized his operation. “These chicks are our natural enemy,” he wrote in a leaked memo. “What I want is a devastating piece that takes the militant feminists apart. They are unalterably opposed to the romantic boy-girl society that Playboy promotes.” Sure, there’s objectification, wage inequality, and sexual violence, but what feminists really hate is romance.

He’s Buried Next to Marilyn Monroe

Marilyn Monroe's crypt

(Library of Congress/Wikimedia Commons)

In 1992, Hefner bought the cemetery vault next to the one containing the remains of Marilyn Monroe, who was humiliated by Playboy after nude photos she’d posed for early in her career that she never thought would be published made her the magazine’s first and very unwilling cover model. Hefner had an entire family and never even met Monroe, but he thought she was hot, so no matter how much she’d hate it, she’s stuck with him forever.

Top image: Luke Ford/Wikimedia Commons

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