The Untold Truth Of Hugh Hefner

Speaking to The Telegraph in 2009, Hefner revealed that the idea for Playboy magazine was influenced in part by America's gradual shift back to a conservative culture at the end of World War II.

"I looked back on the roaring Twenties, with its jazz, Great Gatsby and the pre-Code films as a party I had somehow managed to miss," he told the magazine. "After World War Two, I expected something similar; a return to the period after the first war, but when the skirt lengths went down instead of up I knew we were in big trouble. It turned out to be a very conservative, serious period — socially, sexually and politically."

"I just thought there was another way of living a life," he continued. "Under all the conservatism and the repression there was this yearning for something different. That's the reason the magazine was successful, why people embraced it from the very outset."

Hefner, who was born in 1926 to conservative parents to whom he referred as being "very repressed," also said his time working as a promotional copywriter for Esquire helped shape his soon-to-be iconic magazine. "Esquire was always for older guys, but ... it was very much devoted to male bonding and outdoor adventure," Hefner told CNN. "And I wanted to read a magazine that was a little more sophisticated and was focused really on the romantic connection between the sexes from a male point of view."

Although his name became synonymous with women and sex, Hugh Hefner was actually a bit of a late bloomer. According to The New York Times, he did not masturbate until he was 18 years old, and did not actually lose his virginity until he was 22. According to the Times, Hefner "wielded fierce resentment against his era's sexual strictures, which he said had choked off his own youth."

He said his first time was with the woman who would become his first wife, Millie Williams, with whom he engaged in "two years of foreplay" before sealing the deal, according to The Sun. In that same interview with The Sun, Hefner revealed he was saving himself because, at the time, he was serving in the army while his wife was studying in college.

Maybe he feels like he missed out on something in his youth, but the guy apparently made up for lost time because he supposedly went on to bed more than 1,000 women, but who's counting? "How could I possibly know? Over a thousand, I'm sure," Hefner told Esquire (via The Huffington Post) when asked about his number. "There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn't married. You have to keep your hand in."

Hefner's third trip down the aisle proved to be more tumultuous than the others.

In June 2011, just five days before he was set to marry 24-year-old Playmate Crystal Harris, Hefner confirmed on Twitter that the wedding had been called off, claiming, "Crystal has had a change of heart." Harris would later confirm as much in an interview with Ryan Seacrest, although she also claimed the decision had been "mutual."

Unfortunately, that was just the beginning of the drama. In July that year, Harris went on Howard Stern's radio show, during which she alleged that she only had sex with Hefner once during their relationship and that it lasted "like two seconds." "Then I was just over it," she said, according to People. "I was like, 'Ahhh.' I was over it. I just like, walked away. I'm not turned on by Hef, sorry."

Hefner denied Harris' claims, later telling The Hollywood Reporter that they had sex "once a week." "We had sex with her and a girlfriend," he revealed. "We had sex the first night that we met, with another girl, and it was such a nice relationship that I kept them both over for a weekend."

And yet, miraculously, Harris confirmed in June 2012 that they had reconciled and were back together. They married on New Year's Eve that year, reportedly after signing an "ironclad prenup." Ah, romance!

According to TMZ, Hefner is buried in the crypt next to Marilyn Monroe's at the Westwood Village Memorial Park in Los Angeles, Calif., which he purchased for $75,000 in 1992.

Monroe, of course, was featured on the cover of the very first issue of Playboy after Hefner found an old nude photo of Monroe and purchased it for $500. 

"Jay Leno suggested that if I was going to spend that kind of money, I should actually be on top of her," Hefner later said, according to the New York Daily News. "But to me there's something rather poetic in the fact that we'll be buried in the same place. And that cemetery also has other meanings and connections for me. Friends like Buddy Rich and Mel Torme are buried there. So is Dorothy Stratten."

We're not so sure his eternal resting spot is quite so poetic to Monroe, considering he reportedly didn't get her permission to her photo in his magazine.

In 1985, Hugh Hefner was hit with another bout of bad luck when he suffered a mild stroke. He blamed the stroke on the 1984 book The Killing of the Unicorn by Peter Bogdanovich, which covered the murder of former Playmate Dorothy Stratten by her estranged husband.

"[My stroke] resulted from stress developed over the last year in reaction to the pathological book written by Peter Bogdanovich," Hefner said in a statement, adding that his recovery was "total and something of a miracle."

Perhaps unsurprisingly, Bogdanovich scoffed at Hefner's words. "Confronting Hugh Hefner with the reality of his life and in particular what he and his magazine do to women apparently is something he can't face," Bogdanovich said in his own statement to the Chicago Tribune. "I'm sorry if making him face it had something to do with making him sick."

"I feel a lot worse for the human cost paid by all the women who don't issue press releases. It would be a real miracle if his life would change to benefit women," he added.

Ouch.