15 Ways Hugh Hefner Was Even Creepier Than You Thought

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

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.”

14 They Had a Curfew

With the exception of specific “going out nights” when Hefner paraded his girlfriends around town before bringing them home for weird ritualistic group sex, which was just a whole other thing, his girlfriends had to be home by nine p.m. Otherwise, according to one woman, they were told they would have to sleep on the lawn. Breaking any rule, even once, also meant getting kicked out.

13 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.

12 He Controlled Their Medical Decisions

After less than a year at the mansion, Madison was so depressed that she was contemplating suicide, but she says Hefner refused to allow her to see a therapist. All she could do was get antidepressants from her regular doctor.

11 He Recorded Everyone Without Their Consent

According to several former residents and employees, everyone who visited the mansion was photographed and videotaped, often without their consent and in compromising positions. Whether these tapes functioned as potential future blackmail material or just to get Hefner off isn’t clear, but does it really matter?

10 He Refused to Use Condoms or Do Anything to Prevent STDs

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.”

9 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.

8 Bunnies Say They Were Drug Mules

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.

7 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.

6 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.’”

5 He Was Obsessed With the Manson Family

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.

4 He May or May Not Have Committed Bestiality

One ex-girlfriend claimed she caught him, quote, “ to our dog,” and he simply responded “Dogs have needs,” when she asked just what the hell was going on. “I never left him alone with the dog again,” she said.

3 He May or May Not Have Owned Snuff Films

The same ex-girlfriend claimed he told her he liked watching snuff films, and though it’s not clear whether he actually owned what he at least believed to murder footage or just liked to tell people he did, does it really matter?

2 He Tried to Silence Feminist Critics

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.

1 He’s Buried Next to Marilyn Monroe

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