Hef's Little Black Book

Part 1
The Chase

Of Pursuit and Romance

Part 2
Hefstyle

The Mansion Life

Part 3
The Great Indoors

Hef’s World of Film, Food, and Adult Games

Part 4
The Business of Life

Dreams and the World

Part 5
Inside the Bedroom

Making Love Like the Master

Epilogue

How to Live Long and Influence Playboys

Acknowledgments

Copyright

About the Publisher

Of Pursuit and Romance

The high school dream girl that got away, Betty Conklin
.

T
he one he loved first did not love him back.

They jitterbugged together and laughed together, and his heart leapt whenever he saw her, whenever he thought of her. But she did not love him back. This was the summer before his senior year of high school, and she had asked another boy on a hayride, and he would never be the same because of it. “I turned myself into a different guy,” he would recall. This different guy was self-assured, a dapper fellow whose new wardrobe bespoke his reinvention—the jaunty flannel shirts, the yellow cords, the saddle shoes. He now wrote for the school paper under the byline Hep Hef. He also wrote songs and drew cartoon strips that chronicled the arc of his young life and his young loves. He learned then that he lived largely to be in love, to pine, or to yearn. He learned that his heart felt best when aflutter. Of this time, a classmate buddy of his later remembered: “His interest in girls was intense. Hef was constantly falling in love, one girl at a time, and would be smitten for maybe a month or so. If he wasn’t in love, he felt incomplete and unhappy.”

This would never change. The boy was father to the man he would become. And the man he would become loved women, one after another ad infinitum, with the wide-eyed
exuberance of the boy in saddle shoes. As a man, he would be almost naive in love, giddy and intense—one friend aptly nicknamed him High School Harry, this in his fifth decade—and yet the ad infinitum would also make him aware in love. He would repeatedly declare: “My life has been a quest for a world where the words to the songs are true.” He meant the love songs of yore, the dreamy ones, the ones Sinatra and Billie Holiday sang while caressing the microphone and suggesting bittersweet romance. Such romance had already been the foundation of his empire. Also, he would say, “For me, being in love is the very essence of being alive.” And “I think life is deadly dull when a relationship becomes routine and boring.” And “I admit that I’m still the same romantic pushover I was when I was young.”

While there would be sexual adventures beyond reckoning and well-nigh-innumerable bedmates, he always pursued primary relationships that filled him with fierce longing (even while openly straying therein; he did, after all, have a reputation of epic proportions to uphold). He had romanticized his first marriage to high school sweetheart Mildred Williams until he realized that the romance had faded, that he was not built for marriage after all: “It was a period of dreams lost, dreams set aside—trying to follow a different road, a road not charted in my own terms.” He created
Playboy
so as to re-create himself, just as he had done at Steinmetz High School in Chicago. His magazine gave him license to play again, and his long-term playmates
in the decades that followed—his Special Ladies, as he would call them—gave him reason to swoon head over slippers. He said in the autumn of 1968, at age forty-two, “I’d rather meet a girl and fall in love, and have her fall in love with me, than earn another hundred million.”

In fact he had met that girl months earlier on the set of his syndicated television show
Playboy After Dark.
She was a petite eighteen-year-old coed who resembled the one he had loved first, the one who did not love him back. This girl, however,
would
love him back, famously so. Her name was Barbara Klein, whom he would rename Barbi Benton in the pages of
Playboy
. Over the next eight years she would become the extra-special lady that people thought of most whenever they thought of Hef in love. “Barbi became a kind of Hollywood version of the teenage romance I never really had when I was in high school,” he said later. “I was crazy about her.” On the night that they met, he danced with her to the song “This Guy’s in Love with You.” He softly sang the lyrics into her ear and, as ever, believed those lyrics were true.

W
hen You Know for Sure, You Know for Sure

B
eing in Love Feels Far Better Than Not Being in Love

“A romantic relationship for me is an escape from the challenges and problems I face in my work,” he once said. “It’s a psychological and emotional island I slip away to.” Rarely has he been cast adrift from any such island for very long, as he indicated in a memo to his attorney in early 1988: “Throughout the 1960s, 1970s and 1980s I have had a series of serious romantic, live-in relationships that included Cynthia Maddox, 1961–1963; Mary Warren, 1963–1967; Barbi Benton, 1969–1976; Sondra Theodore, 1976–1981; Shannon Tweed, 1981–1983; and Carrie
Leigh, 1983–January 1988.” The reason for the memo, incidentally, was in response to a misbegotten and quickly dropped $35 million palimony suit filed by Carrie Leigh, the most tempestuous and sexually omnivorous of all the Special Ladies who had inhabited a Playboy Mansion with him. (To wit: “All of these women knew full well that there was little or no possibility that I would ever consider marrying again,” he had added.) The point being, he is lousy at alone and worse than ever when not in love.

Thus it was in January 1988, two weeks after Miss Leigh had left him under a thundercloud of false accusations (no matter that she had for years been taking other lovers in wide variety), that Cupid drew bow upon him once more. The Playmate of that Very Month of that Very Year happened to be boarding at the Mansion Guest House while working on a pictorial with photographer Helmut Newton. Her name was Kimberley Conrad—a blonde, twenty-four-year-old no-nonsense “Alabama-born, Vancouver-bred angel” (per Hef)—upon whom he had cast his wide High School Harry eyes and all of a sudden sensed renewal attendant. She rebuffed his invitations to a pair of Mansion Movie Nights—French art films, no less—until he approached her once again after the second movie ended, as she lounged on his lavish premises. “I told her that I was really interested in her and would like to spend some time with her,” he would recall. “And she said, ‘Well, I don’t really know you.’ And I said, ‘How are
you going to get to know me if we don’t spend some time together?’” (Hef’s line!) “And that line, the simple logic of it—from that moment on, everything changed! We spent that evening together. If this had been a movie, that night there would have been strings and perhaps a little Bobby Hackett horn.”

Mr. Playboy attempts the Improbable: taking Kimberley Conrad to be his “Playmate for a Lifetime.”

On July 1 of the following year, she became the second Mrs. Hugh Marston Hefner. Certain lines apparently work better than others.

I
t’s Not What You Say in a Pickup Line but What You Don’t Say

T
ry Not to Try Too Hard

S
ay It When You Know It— As Long As You Truly Believe It

Eagerness in love would always be both his blessing and curse. It had failed him with his fateful high school crush—her name, by the way, was Betty Conklin—although he harbored vestiges of that crush for years to come. (Poetically, five decades after high school, as his marriage to Kimberley Conrad unraveled, it was Betty Conklin that he kissed—platonically, of course—at the stroke of midnight to welcome in January 1, 1998, when she came to his annual Mansion New Year’s Eve bacchanal.) “Betty represented to me the fulfillment of all my boyhood dreams,” he would note. “I projected everything that I was interested in, everything I had observed in my life, all the dreams that I had extracted from movies, all of this onto her. She couldn’t possibly have lived up to that. It was an illusion.”

The dreams he projected onto Barbi Benton, however, would stick better, if only because he became wise enough to learn some patience. While there was a twenty-four-year age difference stacked against them, patience and a knack for playing games of the heart only emboldened his resolve to capture hers. For instance, she wouldn’t allow him to bring her back to his Sunset Boulevard penthouse alone: “That would’ve been a mistake! I had high morals and didn’t want to be taken advantage of, so I thought that the best way to avoid that was to go out and be among people with him.” He played along, didn’t push too hard, even acceded to her unwillingness to let him pick her up at her UCLA dormitory (in his limousine, natch) for their dates. “I always
drove my own car to meet him at restaurants or clubs,” she would say. “But whatever he was doing, he was charming me. He had much more charm than the boys I saw in college. He was wonderful and cute, even though I thought he was too old.”