Hugh Hefner: 10 Truths Behind the Playboy Legend

Few men have been as mythologized in their own time as Hugh Hefner. But, as with any flesh and blood person, there’s a difference between the fantasy and the reality and as THR‘s executive features editor Stephen Galloway discovered during his time at the Playboy Mansion, sometimes the dissonance can be shocking.

Galloway spent time with Hefner at his weekly movie night and in his legendary bedroom and came away with some totally unexpected insights.

Here are 10 surprising revelations from this week’s THR cover story:

1. EVEN AT AGE 85, HEFNER CAN STILL HAVE A (VERY) ACTIVE SEX LIFE

“We had sex once a week,” Hefner says of his ex-fiancee, 25-year-old Crystal Harris. “We had sex with her and a girlfriend. 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.”

2. HEFNER AND GLORIA STEINEM ALMOST DATED

These days, the feminist activist is more likely to be criticizing the Playboy founder (in fact she called the NBC series The Playboy Club a “net minus”) but back in the day, Hefner says they had a much warmer relationship. “Gloria and I go back a long ways,” he notes wryly of the woman who went undercover as a bunny then wrote about her experience, “but it’s more personal than you probably know. She worked as Girl Friday for Harvey Kurtzman, who created Mad magazine, and he said, ‘You gotta meet this girl, she’s just like you: She can make a guy jump through hoops.’ We actually exchanged phone calls and came very close to dating.”

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3. THE PLAYBOY EDITOR WOULD RATHER SCRAPBOOK THAN WRITE ABOUT HIMSELF

Hefner spent more than a decade working on his memoirs before abandoning them altogether. However, he has continued to scrapbook his life. Today he has a collection of 2,485 volumes of scrapbooks. It’s a stunning archive detailing almost every aspect of his life, done with a deliberateness that indicates Hefner knew early on he wanted a legacy. It contains the good, the bad and the ugly: photos of Hefner at the beginning of Playboy, which he started in Chicago in 1953 after scraping together a few thousand dollars for a magazine that would have been called Stag Party if the title hadn’t been taken; a copy of the famous nude Marilyn Monroe photo that graced the first issue, which sold 54,000 copies; critical articles about the death of Dorothy Stratten, a Playmate of the Year who was shot to death in August 1980 by her estranged husband, Paul Snider; and, somewhat weirdly, a psychologist’s assessment of her lover, director Peter Bogdanovich — a scathing Hefner critic — whose origins not even the archivist can explain.

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4. HEFNER’S BEDROOM IS A MESS

Old magazines and papers litter the floor all around his giant, king-size bed, with its kilim-style comforter. There are notes on an upcoming movie he will screen at one of his famed movie nights; pages from his magazine; a New York Times book review and wads of documents only Hefner could possibly identify. It’s an intimate window into one man’s unvarnished id, and at odds with his empire’s sexual theme: Two couches are covered with hundreds of stuffed toys; there’s a mantelpiece highlighting Frankenstein heads and a framed replica of a toy gun he had as a child; the whole place is crammed with relics from his past. “I can be at my most creative like this,” Hefner explains.

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5. THE MAN WHO DATED ‘THE GIRLS NEXT DOOR’ MAY PREFER BLONDES, BUT HIS HEART LIES WITH A BRUNETTE

His tastes then and now veer toward women who remind him of the movie stars he loved growing up, such as Alice Faye, though he currently favors blondes. “Picasso had his pink period and his blue period; I’m in my blonde period,” he quips, though the woman who got closest to him, Barbi Benton, was a brunette. None of them was his intellectual match. “I’m not looking for a competitor,” he says. “I’m looking for a partner -— a romantic partner.”

6. WHILE PLAYBOY’S DOMESTIC FORTUNES SHRINK, THE MAGAZINE FLOURISHES WORLDWIDE

Playboy Enterprises Inc. lost $51.3 million in 2009. Ad pages have shrunk by over half in the last decade and its circulation has dropped from a high of 7 million to 1.5 million. But in just the past year, Playboy has added three international editions to its previous 28. Playboy Enterprises CEO Scott Flanders says the American version of the magazine “loses a small amount,” but that Playboy makes money from its international print operations.

STORY: Hugh Hefner: A History of Romance

7. PLAYMATE AND EX-FIANCEE CRYSTAL HARRIS CRIED TO HEFNER AFTER TALKING ABOUT THEIR SEX LIFE ON HOWARD STERN’S SHOW

“I was very surprised,” he admits. “She was talking about a third person I didn’t recognize. She felt very badly about it afterwards. She came over and wept. You know, she’s the one that wanted to get married, not me. But I think that Crystal is more than one person; she’s kind of lost at the center and was overwhelmed by the relationship, and got caught up in an affair while we were going together that I knew nothing about.”   As to the way they parted: “There was no disappointment in terms of not getting married -— it’s the disappointment of the relationship going south,” he says. “It wasn’t that I wanted to be married; what I wanted was continuity. But I misread the signs.”

VIDEO: Hugh Hefner’s Ex, Crystal Harris, Spoofs Their Age Difference

8. HEFNER DOESN’T TALK ABOUT DEATH

He hardly ever talks about death, a close colleague says: “Even when [a longtime assistant] died, after the memorial, he never mentioned her again.” Is he afraid of the prospect? “No,” insists Hefner, an agnostic who professes no faith in any afterlife. “My mother lived to 101.”

9. PLAYBOY HAS NO SUCCESSION PLAN SHOULD HEFNER PASS AWAY

When asked about the succession plan, Flanders gives an agonizing pause. Finally he says: “That’s hard to imagine. [There’s] no succession plan.” Hefner’s own hopes that one of his two younger sons —- Marston, 21, and Cooper, 20 (with Conrad; he has an older son as well as Christie, 58, with his first wife) —- might take over seem unfounded. “At one point, I expected it to be a family thing,” he admits, “but that’s been squandered.” He rephrases the wording. “I don’t think that’s in the cards anymore.” Both boys are still in college and neither has yet had Hefner’s daughter Christie’s experience of joining PEI as a junior executive before climbing to the top.

10. HE GETS LETTERS FROM WOMEN AROUND THE WORLD WANTING TO BE HIS GIRLFRIEND

When girls apply, Hefner checks out their pictures and invites some to visit. Those he likes remain. “I’m obviously a visual person, and looks and appearance are important, but it’s pretty obvious also that I have a particular type,” he acknowledges. Does he not think these women may partly be lured by his money and power? “Of course,” he says. “But what is anybody really attracted to?”

For more, read the full cover story now and read about all the aspects of the Playboy empire here.