Hugh Hefner's Most Controversial Moments

For some, Hugh Hefner was a trailblazer. For others, an exploiter of women.

The Playboy founder died on Wednesday at the age of 91. His Playboy magazine helped usher in the '60s sexual revolution and published the first photos of nude female centerfolds. On a personal level, Hef championed topics considered controversial during certain eras: Civil rights, women's rights and LGBTQ rights, birth control and sexual freedom.

He also made headlines over personal and career-related controversies.

Playboy Is Launched and Not Everyone's Happy: Hef published the first nude female centerfolds in his magazine. The first issue was published in December 1953 and featuring naked pics of Marilyn Monroe.

The magazine soon drew anger from feminists as well as religious people. Such criticism continues to this day.

Hef vs. Feminists: "These chicks are our natural enemy," Hef wrote in an internal memo in 1970. 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."

Obscenity Charges: Hef was arrested on charges of publishing and circulating obscene literature due to the Playboy June 1963 issue, which featured Jayne Mansfield. He was acquitted.

Playboy Bunny Rules: Feminist icon Gloria Steinem went undercover as a Playboy Bunny in the '60s, writing in a Show magazine exposé that she was told, "We don't like our girls to have any background, we just want you to fit the bunny image."

She also said the women had to abide by strict rules and would have their pay docked if they ate on the job or if their underwear was showing, writing, "I think Hefner himself wants to go down in history as a person of sophistication and glamour. But the last person I would want to go down in history as is Hugh Hefner."

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Hef's Multiple Girlfriends: Hef was married three times, most recently to Crystal Harris, 31. When he was separated from his spouses, he dated and in his senior years, had multiple live-in girlfriends.

He told Esquire in 2013 he has slept with "over a thousand" women.

"There were chunks of my life when I was married, and when I was married I never cheated," he said. "But I made up for it when I wasn't married."Ex-Girlfriends Tell-Alls: In her 2015 book Down the Rabbit Hole, his ex Holly Madison depicts the Playboy founder as controlling and manipulative. She said they were given an allowance, meals and rooms at the Playboy Mansion and were expected to have sex with Hef, in front of each other, even though they denied it publicly. She said they were given a 9 p.m. curfew and were not allowed to date other people, despite the fact that he was not monogamous. She also accused him to pitting the women against each other.

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In a statement, he responded, "Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can't win 'em all!"

Other ex-girlfriends have also written about their time at the Playboy Mansion and about having sex with Hef, including Jill Ann Spaulding in her 2004 book, Jill Ann: Upstairs.

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Wild Playboy Mansion Parties: The bashes were the place to be, especially if you liked scantily clad Playboy bunnies, alcohol and drugs.

Bill Cosby Controversy: In 2016, a woman named Chloe Goins, a former model, claimed Cosby sexually abused her at the Playboy Mansion and sued Hef for allegedly conspiring with him in 2008 to commit sexual battery of a minor.

In 2014, another woman, Judy Huth, accused Cosby of sexually assaulting her after drugging her in the Playboy mansion in 1975 when she was 15.

"Bill Cosby has been a good friend for many years and the mere thought of these allegations is truly saddening," Hef said in a statement at the time. "I would never tolerate this kind of behavior, regardless of who was involved."

Cosby has denied any wrongdoing. He currently awaits a retrial over unrelated sexual assault allegations. 

Rape Accusations Against Hef: In his 1984 book The Killing of the Unicorn: Dorothy Stratten 1960-1980, movie director Peter Bogdanovich accused the Playboy founder of forcing himself on Playboy Playmate Dorothy Stratten sexually in his Jacuzzi "grotto" on her first night at the Playboy Mansion.

Hef said in response, "I am, publisher of Playboy or no, a very shy man. And I could no more force myself on a woman, psychologically or physically, than could the man on the moon," according to Rolling Stone. No charges were filed.

Hef suffered a stroke in 1985 and told reporters he blamed Bogdanovich for causing the stress which led to it.

Bogdanovish had also written that Stratten, his former partner, who was shot dead in 1980 by a man she married, "could not handle the slick professional machinery of the Playboy sex factory, nor the continual efforts of its founder to bring her into his personal fold, no matter what she wanted."