Hef's girlfriends

(Romantic (Retrospective

ou should know they all became his because he was nothing like they had imagined. The way he is—especially with females, those who seize his heart and all others who simply enter his orbit—has forever defied predictable expectation. Yes, for sure, he brashly helped free the world from sexual repression and societal hypocrisy. And yes, he boldly prefers to function in only pajamas (or less) rather than wear conventional clothes, but—and why should this be so hard to fathom?—where women are concerned (and no question, women are always his concern), he is the opposite of brash or bold. Or swaggering. Or even slightly slick. You wonder, then, what instead approximates the magnetic mixed-company comportment of our one and only original Mr. Playboy, of our legendary rebel icon whose sheer breadth of bedroom conquests has fueled mass fantasy across generations in the extreme plural? After all, as he himself has put forth, "I said a long time ago a lot of people buy the magazine for the articles, but it's the Centerfolds they remember. And I think that's

Janet Pilgrim (1955) "Janet was a secretary at the Playboy offices in Chicago," says Hef. "She was our first girl-next-door Playmate. That's me standing in the doorway in the background."

true in terms of my life—they remember all the pretty ladies." Meaning specifically his very own pretty ladies, as in, the collective coterie of preeminent regal consorts ever shimmering at his side throughout the decades (within camera range or, more blissfully, shrouded from it). Of course, no one will ever remember them the way he can and does, all things considered. Because, beyond the unique fame that accompanied their respective tenures as his most preferred company, each of them in turn fortified his spirit as nothing else ever would. Not that any of them, at least upon arrival in his world, could have foreseen how profoundly he would respond to their essence, how they would gain access to the secret holdings of that newly reinforced spirit— his selective stash of private dreams eternally golden and also thereby unashamedly and glamorously olden.

Still, it's not as though we haven't been plied with clues aplenty to the twinkling allure of the innermost Hefnerian spirit. Take, for example (please?), his trademark time-tested,

Joyce Nizzari (1958—1960)

"Joyce was a teenage model when we first met in Miami. She was one of our first Playboy Club Bunnies. We've stayed in touch, and she now works as a secretary for me at the Mansion more than half a century later."

Cynthia Maddox (1961-1964)

"She was my cartoon editor in Chicago and our most popular cover girl in the 1960s, appearing on the cover five times."

I

Donna Michelle (1963-1964)

"Donna and I had a brief but truly memorable affair. She was the most popular PMOY of the 1960s."

Double Trouble in Paradise

Just once upon a time, there co-existed two number one Hef ladies-perfect opposite dream girls, each of whom had simultaneously staked claim to his heart. "No question that it's possible to be in love with two women at the same time—I've been there," Hef concluded, in­voking that high-flying, subdivided bedroom farce-a-thon he christened his Captain's Paradise, after the 1953 film wherein a sea captain played by Alec Guinness keeps a different lover in two ports. Hefs version: In spring 1971—three years into Hefs routine of uprooting himself from the Chi­cago Mansion for essential Los Angeles nestling with Barbi Benton, his first truly iconic Special Lady, who weeks earlier had dis­covered what became Playboy Mansion West—the luscious,

platinum-haired Karen Christy entered Hef's Chicago living room and also his heart. What ensued, until early 1974, racked up the air miles on Hef's black Big Bunny DC-9 as he made biweekly commutes to indulge each woman (and himself) while hiding all traces of one from the other. Time magazine blew his cover with a report that pictured him in both mansions, snuggled with the leading lady of each household, pronouncing him "long a two-of-everything consumer." Both women split,

though Barbi returned for a couple more years. "In the movie," Hef lamented, "the arrangement ended in disaster, with both loves leaving him. How could I expect any better conclusion?"

Christa Speck (1961-1962)

"Christa was a special favorite of mine—and a favorite of our readers as well."

Barbi Benton (1968-1976)

"Barbi was the most important romance of my| life up to that time."

Hope Olson and Patti McGuire (1975-1979)

"We had some wild and wonderful times together."

Lillian Mullor (1975-1976)

"A Scandinavian stunner. We're still close."

starry-eyed credo that will never go away: "My life," he will repeatedly tell you, "has been a quest for a world where the words to the songs are true." Sentimentalist supreme, he'll recite that idyllic refrain at any given opportunity—dreamily, liltingly, dependably. He alludes, of course, to those heady if naive moon-June-swoon-croon tunes of his storied unyielding youth. But with due respect, you must eventually come to realize that the reason he keeps saying it is because he keeps meaning it, keeps questing for that illusory lyrical world, keeps seeking to stoke his perpetual schoolboy heart with fixes of seismic lovesick fluttering, fresh and pure. (For a college-era scrapbook he once adorned the margins around a photo of himself and his nubile date at a formal dance with a deftly hand-printed graffiti gush of sentimental song titles: "That's How Much I Love You, Baby," "I Got a Gal I Love," "When Am I Gonna Kiss You Good Morning?") With each successive infatuation, way back then and ever after, he would be serially reborn,

Karen Christy (1971-1974)

"Captain's Paradise! A truly passionate affair that came in the middle of my rela­tionship with Barbi."

Sondra Theodore (1976-1981)

"A true girl next door."

I

Shannon Tweed (1981-1983)

"Shannon was a major love, as well as a major Playmate of the Year."

reanimated, reinvigorated. "Hef was constantly falling in love, one girl at a time," recalled an old classmate pal many years later, "and would be smitten for maybe a month or so. If he wasn't in love, he felt incomplete and unhappy."

And so encapsulated the legacy at core: The boy who became father to the man launched his lifelong insatiable (if seemingly unrealistic) romantic questing very early on— with white-hot determination so inflamed that it would inevitably spark the creation of a certain Rabbit-Headed empire—never to cease or even taper off just a little. Except he eventually learned to lengthen his fleeting monthlong crushes of yore so as to stay happily smitten for years at a time (and usually, somehow, for always), thanks to the majestic wiles of those most special ladies who would compose his sublime cavalcade of primary relationships. And who,

Carrie Leigh (1983-1987)

"She was trouble, but I was smitten."

Kimberly Conrad (1988-1997)

"I married the girl, but it didn't last. We remain very close, and we have two great sons."

not coincidentally, are now being dangled here before your eyes to best illustrate what inspired the greatest smites of Hugh M. Hefner's life. (Connoisseurship has its rewards, don't it?) Indeed, long after he'd become the most famous sybarite mogul on the planet, he made clear that the only actual currency that mattered to him was love. "I'd rather meet a girl and fall in love, and have her fall in love with me, than earn another $100 million," he declared, minus any hyperbole, during a rare fallow-hearted period. (Such fallow periods for him never lacked in bedmates galore; rather, he'd just temporarily find himself lacking that singular requisite true-love mate over whom he could adoringly obsess day and night.) His radar, nevertheless, served him magnificently, and always his style upon target approach would impress each new candidate as courtly, attentive, debonair, authentic, whimsical, uncharacteristically patient and maybe even a tad shy—i.e., the sum parts of lethal charm. One lover's testimony: "Whatever he was doing,

Sandy and Mandy Bentley (above) and - Brande Roderick (right, 1998-1999)

"They were a perfect antidote after the breakup of my marriage."

Tina Jordan (left, 2000-2001)

"Tina was one of my favorites among the girls I was seeing at the turn of the century. There were seven full-time girlfriends at one time."

Holly Madison (2001-2007), Bridget Marquardt (2002-2007) and Ken-dra Wilkinson (2004—2007) "The romance was as sweet as it seemed on The Girls Next Door, and I remain close to all three of them."

he was charming me," averred Barbi Benton, perhaps his most indelibly classic lady love (1968-1976), who was an 18-year-old UCLA coed when they met. "He was wonderful and cute, even though I thought he was too old." (Theirs, by the way, was a mere 24-year age difference—which would melt away as have all such ever-broadening time chasms in his repertoire—but we'll get to that soon enough.)

Not insignificantly, one of his secretaries noted decades ago: "He imagined at every party that he would see a girl across a crowded room, their eyes would meet, violins would start to play, and he would feel that pit-a-pat." And typically, that's exactly how it has worked, right down to the onset of pit-a-pats. With Barbi, for instance, he spied her across the set of his Playboy After Dark TV series, and within hours she danced (continued on page 144)

Anna Sophia Berglund (2008-2012)

"A sweet lady who helped me over some bumpy spots."

Shera Bechard (2011-2012)

"An elegant French Canadian.

Crystal Harris (above, 2008—2011/2012— )

"The runaway bride is back. We're happy, but Chelsea Ryan and Trisha Frick are here as well—just in case."

GIRLFRIENDS

(continued from page 121)

in his arms to the Burt Bacharach standard "This Guy's in Love With You," the lyrics of which had never felt truer to him. But of course. Similarly, on the night he first got an eyeful (and more) of 19-year-old former Bible-school teacher Sondra Theodore (1976-1981), he swayed her to the slow-jam strings of Barry White's "Baby Blues" and—voila: "At that point I was a goner," she confessed. "No one can slow dance like Hefner. It was like the Red Sea parted." (Soon after, he draped her decolletage with a diamond-encrusted necklace that spelled out the words Baby Blue.) Kismet would be his specialty—spontaneous love combustion—and those who knew him best could spot its every outbreak, so recognizable were the symptoms. "It was much more than lust at first sight," stressed his old friend John Dante, a Mansion habitue who witnessed the phenomenon repeatedly. "Romance was foremost on his mind."

Actually, while Dante's instant-inferno-effect summation uniformly applies to the dawn of each serious Hef relationship, you should know that the quote above refers specifically to Karen Christy (1971-1974), whose arrival at the Chicago Playboy Mansion rendered the master intractably thunderstruck. His own inimitable sizing up of Ms. Christy, whom he crowned Miss December in their first year together: "A voluptuous, baby-faced blonde from Texas who had stepped right out of my erotic, pre-code Busby Berkeley Hollywood dreams from boyhood." (He went so far as to add, "When I fell for her, I fell hard," evincing that theirs "was the most passionate love of my life—while it lasted.") Which prompts us to now address how, and why, so many of his special ladies have gotten to the heart of Hef as others never could. "My love map," he has said, "is very much designed and written by Hollywood. I was a Midwestern Methodist boy from Chicago—but the other dominant half of my identity came directly from those larger-than-life dreams I saw in the movies." More often than not, in fact, he has spotted in his choicest mates irresistible traces of vintage silver-screen goddesses—Alice Faye, Jean Harlow, Marilyn Monroe—who had all jolted his adolescence with carnal stirrings that stir no less powerfully these days. ("First you look at the face," he once informed me, apropos of all initial encounters wherein his subconscious sifts for any such nostalgia-gilded resemblances.) Barbi Benton, he concluded, "became a kind of Hollywood version of the teenage romance I never really had when I was in high school. I was crazy about her." Further, she was more than just the first truly necessary primal enticement that had him returning repeatedly from Chicago to Hollywood—via his famously customized all-black Big Bunny private DC-9. She also happened to discover the Shangri-la property—right across the street from Bogart and Bacall's old place—that became Playboy Mansion West, where, as its irrefutable very first lady, she lovingly oversaw the fabled homestead's Hefnerization metamorphosis

in between his increasingly frequent commutes to the dreamland whose stars had shaped him.

Poetry, thus, lurks in his early proximity to the ghost house of Humphrey Bogart, whose love-torn character in Casablanca (Hef's favorite film) reminds him of himself whenever any of his grandest loves are upended. Romanticized Hefner touchstone therein: the scene in which Bogie stands alone in the rain reading Ingrid Bergman's farewell letter while its ink soggily bleeds out, much like the heart beneath the stoic hero's trench coat. "We've all been there," Hef once confessed to me. "We've all had our punches in the gut." And for certain, in recent years he has very publicly absorbed a couple of especially rough blows in the special lady department—the first one landing with the departure of his ultra numero uno among that original troika of The Girls Next Door, the telegenically devoted Holly Madison (2001-2007), whose visceral adoration was more than reciprocated by him and broadcast worldwide during five seasons of the E! network's Mansion-based hit reality series (on which she ostensibly shared him, to a point, with spritely supplemental girlfriends Bridget Marquardt and Kendra Wilkinson, who both left the same year for outside pursuits). And then two Junes ago there came the jarringly thunderous Runaway Bride incident: Crystal Harris, who had emerged as his steadfast leading lady in the reinvented sixth and final GND season (twins Karissa and Kristina Shannon this time filled the supplemental roles), found herself on Christmas Eve of 2010 happily accepting— gulp!—his (maybe equally jarring) proposal of marriage. However, five days prior to the meticulously planned ceremony, she bolted from the Mansion, overcome by fears real or imagined. ("Ultimately, I fooled myself completely in the relationship," he later told me, "because that proposal was, without any question, a rebound from Holly's leaving. In the process, I probably misread Crystal. And so there went the bride.")

But the larger point here, thematically speaking, is that he withstands such lumps with an enviable philosophical grace not so easily mustered by other mortals. "I've always thought about my life like a movie," he explained, not surprisingly, some years ago as we assembled sage content for Hef's Little Black Book, an invaluable manual created to bolster all dreamers (and reissued this month with updated tales of romance, pain and ongoing wisdom). "You need the drama. If you think of your life that way, you get through the tough times. Plus, the reality is that life—especially in this regard—is very much like a movie. We delude ourselves with the notion that somehow there is only one person out there who is a soulmate. In fact, there are many appropriate people who can be cast in that co-starring role. When you're dealing with lost love, it's time to just start the casting process all over again."

Naturally, then, Hef excels at being his own best casting director—because he has long understood and perfected the epic protagonist character he alone was born to

portray. "It wasn't difficult to figure out that the most successful sex object I'd created was me," he once proclaimed. "It was a role I was very comfortable playing. I have built here what could be viewed as a perpetual women machine." By which he means—due to the nature of his work—there would be no paucity of incoming prospective co-stars to audition as meaningful love interests. (Best criterion for snagging the part, aside from radiant beauty: "Somebody who doesn't want to change me at all." Also, great laughers who are not averse to bright playfulness, general or sexual.) Lately, in fart, he's come to favor ensemble casting, a trend that's been mainly in place after the less-than-sybaritic hiatus that constituted his unwaveringly faithful relationship with Kimberly Conrad (1988-1997), the second-ever Mrs. Hugh M. Hefner, whom he unwittingly mislabeled Playmate for a Lifetime. "I went to the multiple-girlfriend arrangement because a large number of them can't hurt you as much as one can," he would say. Thus, revolving platoons would become the status quo, with certain groupings more memorable than others; his Girls Next Door, of course, are now embedded in the pop-culture pantheon. But who could forget, for instance, that name-rhyming trio made up of the exquisite Brande Roderick and the wily twins Mandy and Sandy Bentley (1998-1999)? Even now, with the return this past spring of the genuinely contrite Crystal Harris as his number one Special Lady, she willingly consented to join the dedicated stock company already ensconced in his affections—Trisha Frick and Chelsea Ryan (who had genially supplanted predecessors Shera Bechard and Anna Sophia Berglund, the heart-rescue team that endearingly dressed the wounds left by Crystal's vanishing act). He was quick to announce this time around, "There are obvious differences. I'm not about to get married. I think that was a dumb idea to begin with. And I'm not giving up my other girlfriends, because I think there is safety in numbers."

Frankly, what could be better news? Because a married Hef is not the same Hef whose phantasmagoric escapades have vicariously sustained the imaginations of admiring men for era upon era upon era. Shouldn't every generation be privy to scrutinize the evolving, exacting standards and predilections of the master at his craft? How else could we have gotten to "meet" and "know" the bounteous likes of special ladies immemorial—the Janet Pilgrims, the Joyce Nizzaris, the Christa Specks, the Lillian Mullers, the Hope Olsons? (These are but a fraction of the pluperfect specimens captured both by him and by the retrospective pictorial you're likely still staring at.) Even he has come to this same satisfying conclusion: "The truth of the matter," he says nowadays with wistful but firm resolve, "is I should be single. I'm better served that way." And so too would be much of the male populace at large, I'm thinking. Adamantly ageless at the age of 86 (propelled by that wide-eyed boy inside him who damn well refuses to entirely grow up),

he has found that marriage for him is a twice-cursed been-there-done-that experiment in illogical confinement. Of his first try at it, with college sweetheart Mildred Williams, he lamented, "It was a period of dreams lost, dreams set aside—trying to follow a different road, a road not charted in my own terms."

Terms changed, delectably so, when in 1953 he launched this magazine with all its built-in accoutrements. And thus, less than a decade after initial blastoff, we can still glimpse him in full swing—because his life had by then indeed become a movie (with several more yet to come) or, in this case, the focus of a defiantly hip award-winning 1962 documentary aptly titled The Most. "I have a certain reputation for being a man about town, a guy continually with a beautiful and ofttimes different chick on my arm, night after night," he suavely informs the camera, propping himself in a stately doorway—all of 35 years old, lithe, self-possessed, sharply tailored, cucumber cool, waving his iconic smoldering pipe like a scepter, lording over yet another jazzy Chicago Mansion bacchanal afforded by his soaring corporate brand, already worth a jaw-dropping $20 million-plus. "I enjoy being with women very much. Most of the girls I date are several years younger than I am—18 to 24, 25, probably." (Famously, his romantic pursuits would never stray far from that same tender-blossom demographic, no matter his own ripening vintage; it's how cyclical rejuvenation always looks and feels best on him. "To a great extent, it's what keeps me alive," he says now. "I love to hear their laughter.") Anyway, he also handed the filmmaker this slippery demurral when citing one newspaperman's estimation "that I had probably made love to more beautiful women than any other man in history. Now, I'm very sure this probably isn't true...."

Actually, now we can probably be very sure that it's likely profoundly true—give or take. Quantity, however, has never been the point—even when his bed has swarmed with six or more bodies. "Something would always happen," Hef explained not long ago, "because I'm essentially a romantic—an unusual romantic, perhaps. But I inevitably found myself becoming truly, emotionally drawn to and involved with just one of the girls, which tended to override the other connections and grow, relationship-wise, into something more focused and traditional." (This was how Holly, for instance, first emerged for him; yes, their eyes met across a crowded bed.) Nevertheless, he quite openly consumed an unending array of new and different flavors during each major romance (the Kimberly Conrad marital years excepted), which rarely went over too well: "He dates other girls and I don't like it," Cynthia Maddox, his first truly serious live-in lady love (1961-1964), pouted on-camera in The Most, with mild impatience that escalated over time, as it always would with his greatest leading ladies. Not that they didn't rationalize away this habitual quirk of his; their love and concern for him were every bit as all-encompassing as his for them. "He was lonesome," semi-empathized

Barbi Benton. "When the cat's away," she added ruefully, "the mice will play." Sondra Theodore tried shrugging it off this way: "The others are just adventures." ("My bed," he'd say, beaming reassurance to all, then and now, "is a democracy!")

"Let's face it, the man knows how to treat women," sighed the lustrous and well-lavished Shannon Tweed (1981-1983), who last year became Mrs. Gene Simmons after decades of common-law togetherness. No, this golden succession of Hef's special ladies moved on and out largely because they could not make him theirs alone, never mind theirs in matrimony. ("Hef getting married was such an absurd idea," recalled Tweed. "We thought it was funny.") And yet he genuinely loved falling in love with each and every one of them, cherished how they individually re-empowered him and never stopped loving them after gently setting each one free to fly on her own. Of course, in doing so, he brought upon himself funks of recurring heartache— from the mid-1950s light-years onward through the latter-day platinum-posse period. "Broken hearts are like broken legs," he once lectured as only he could.

"They needn't be fatal. Only a foolish person doesn't leave the heart open for the joy and pain of love again."

And so he shall persist: "Being in love completes me. I need to be in love." He could not have been more emphatic when he told me those things recently. He knows the romantic perfection he lives to find is perfectly unfindable. But he will never call off the search, because that search is the full yearning essence of who he is, of who he always must be: "I realize that it is the way of things—that people remaining faithful, for instance, turns out to be a long shot. And of course, if one looks for an unrealistic relationship to begin with—because in the passing of the years, I'm looking for relationships with young, beautiful women—that itself is asking for trouble." He paused here and gave a sly omniscient smile: "There's a great old song, the lyrics of which go, 'If love is trouble, that's what I'm looking for.'"

He believes the words to the song are true, by the way. "But," he added in case we hadn't yet figured it out, "at least I'm very consistent."