Playboys
A tale of charmers, chancers and giant peppermills - told by Bob Peirce
In the seventeenth century a ‘play-boy’ was a boy actor in a theatre company. In Ben Jonson’s masque, Love Restored, first performed in 1616, the character Masquerado announces “The rogue play-boy that acts Cupid is got so hoarse, your majestie cannot hear him”. Also known as ‘boy players’, they performed female roles until the Restoration in the 1660s. One of the last of them, Edward Kynaston, was born in 1640 and died in 1712.
In the 1829 novel The Collegians, Irish writer Gerald Griffin uses the term in a flirtatious context. A young lady tells the man complimenting her that he is a “funny gentleman and a great play-boy”. The Oxford English Dictionary credits Irish English with the evolution of the word ‘playboy’ (now unhyphenated) to mean a man, usually wealthy, who leads a life of pleasure, especially one who behaves irresponsibly and is sexually promiscuous.
In early twentieth century Ireland, the word playboy also meant a hoaxer or trickster, or someone who could spin a good yarn. The play Playboy of the Western World by John Millington Synge premiered at the Abbey Theatre in Dublin in January 1907. In it an unprepossessing stranger called Christy Mahon regales pub patrons with a story of how he has just killed his father by driving a spade into his skull and is now on the run. This impresses several of the village women, such is the boredom of their lives in a place where nothing much ever happens. The stranger commands their admiration as a man of action. Disappointment ensues when his father – injured but alive – shows up at the pub. One of the ladies laments that “I’ve lost the only playboy of the Western World”.
The play caused outrage on its first night in Dublin. Arthur Griffith, leader of Sinn Fein, denounced it as “a vile and inhuman story told in the foulest language we have ever listened to from a public platform”. Opening night in New York in 1911 fared no better. The audience booed and hissed. They threw vegetables and stink bombs at the stage, so people clearly came prepared to be appalled. Some reportedly threw rosaries. After this rocky start and helped by support from no less a literary giant than W.B. Yeats, the play went on to become a classic, admired for its masterful use of language.
Two decades later, the image of a playboy soon moved on from bungled attempts at patricide to more glamorous pursuits. The era of the playboy as a well-heeled, stylish hedonist really got underway in the nineteen-thirties. The Wall Street crash of 1929 and the Great Depression that followed it put an end to a period of comparative prosperity. The Roaring Twenties had offered a new variety of entertainment for most people – movies, dance clubs, jazz, amusement parks and more. But in the threadbare-thirties the party was over for all but the lucky few.
Those that could still afford to party were relatively conspicuous. At about the same time, photojournalism was taking off. This was made possible by developments in camera technology. The compact Leica 35mm, introduced in 1925, and the first flash bulbs a few years later allowed journalists new flexibility to take pictures quickly, whenever and wherever opportunities arose. New magazines in the 1930s, such as Life in the United States and Picture Post in England could tell stories in pictures rather than text. They found large readerships who had an appetite for stories of the privileged few.
It was at this time, 1933, that Prohibition came to an end in the United States. Former speakeasys were able to emerge into the limelight and reinvent themselves as exclusive clubs. The Stork Club opened in Manhattan in 1929, with a stork in a top hat as its logo, owned by a former bootlegger called Sherman Billingsley. El Morocco followed in the 1930s and Copacabana in 1940. These and similar ritzy watering holes in London, Paris and elsewhere, were the places to go, to be seen, and to be photographed. The Golden Age of the Playboy had arrived and would last into the 1960s.
Who were the playboys? The epithet was used to describe a large number of men, but the following names pop up on many lists – Howard Hughes, Errol Flynn, Prince Aly Khan, King Farouk, Aristotle Onassis, Jack Kennedy, Juan Capuro, Gianni Agnelli, Jorge Guinle, Gunter Sachs and the luxuriantly named Porfirio Rubirosa.
Some of these cannot be adequately described as playboys, because they had serious accomplishments to their name. Kennedy, for example, undoubtedly pursued a playboy lifestyle of clubs, yachts and multiple female companions. But on the other hand, he was a war hero who became the 35th President of the United States and is credited with saving the world from a nuclear holocaust in the Cuban Missile Crisis of 1962.
Howard Hughes, another pursuer of many women, was an industrialist, a pioneer aviator with multiple records to his name, and founder of a major airline. Aristotle Onassis was a shipping magnate. Gianni Agnelli inherited Fiat when he was only 25 but sensibly took his grandfather’s advice to let the managing director continue to run the company until he was ready to take over. He spent the next two decades devoting himself to pleasurable pursuits, but then took command of Fiat in 1966 and was the pre-eminent leader of Italian industry for the next thirty years.
While there is no agreed definition of a playboy, it might be useful to think of a ‘true playboy’ as someone who does virtually nothing other than seek enjoyment. Longman’s dictionary defines playboy as ‘a rich man who does not work and who spends his time enjoying himself with beautiful women, fast cars etc.’
There was, of course, nothing fundamentally new about a man doing nothing useful and spending his time pursuing women. And there were already plenty of words for them, such as libertine, philanderer, dangler, and rake, which was also applied to women. ‘Don Juan’– a highly-sexed character from a seventeenth-century play by Tirso de Molina – had long been invoked to describe such behaviour. So had Casanova, who, unlike Don Juan, really existed. An eighteenth-century Venetian of modest background, he became bored with training to be a lawyer and took off travelling around Europe, posing as an aristocrat and defrauding people. Thanks to his autobiography Histoire de ma vie, he became best known for bedding multiple women. Beginning with two teenage sisters, he documented a string of 120 conquests; dalliances with men and boys made it into his notes but not into the book. Interestingly, to call a man a ‘Casanova’ today is rather less pejorative than the man himself deserves. He was a fraudster and a conman.
Jorge Guinle needed no such subterfuge. The heir to an enormous Brazilian fortune, he was romantically associated with numerous leading movie stars, including Marilyn Monroe, Jayne Mansfield, Ava Gardner and Rita Hayworth. He led a life of complete self-indulgence and made no pretence otherwise. In an interview in 2002, when he was 86 years old and had burned his way through his entire fortune, he said “the secret to living well is to die without a cent is your pocket, but I seem to have miscalculated”.
Gunter Sachs was a similarly honest playboy. He did not pretend to be anything else. He happily claimed that he had never worked a day in his life. Like Guinle, he inherited a large fortune. His great-grandfather Adam Opel founded the eponymous car company. Gunter partied hard and had homes in Gstaad, St. Tropez, St. Moritz, Munich and Paris. He distinguished himself as a target for paparazzi when he bombed Brigitte Bardot’s house with a thousand roses dropped from a helicopter. This spectacular if unorthodox courtship gambit did the trick and they were married soon afterward, but only for three years. Sadly, Gunter Sachs took his own life in his seventies, at his chalet in Gstaad.
Other notorious playboys died driving fast cars, which somehow seems a more fitting way for fast livers to go. The first of them to go was Prince Ali Salman Aga Khan, known as Aly Khan. His father was Aga Khan III, leader of the Ismaili Muslim community. His grandson is the current Aga Khan V. Aly’s lifestyle was definitely that of a stereotypical playboy. He had a long list of lovers, including the notoriously promiscuous Duchess of Argyll as well as Thelma, Viscountess Furness, who was simultaneously involved with the Prince of Wales. Aly Khan went on to marry Joan Guinness, having been mentioned as co-respondent in the divorce suit filed by her previous husband, British Conservative MP Loel Guinness. Aly continued his philandering and had several extramarital affairs, including one with Pamela Churchill, the ex-wife of Winston’s son Randolph and the consort of many men during a long life, ending as the American Ambassador to France. In 1949, Aly and Joan were divorced after thirteen years and, a few weeks later, he became the third husband of Rita Hayworth. She filed for divorce within two years on the grounds of “extreme cruelty, entirely mental in nature”, and Aly went on to date more women before his death in 1960. He died in a head-on car collision in Paris, driving his Lancia while his chauffeur, strangely, sat in the back.
Porfirio Rubirosa, arguably the prime example of a classic playboy, had a good run from the 1930s until 1965, when he died after driving his Ferrari into a tree in the Bois du Boulogne following an all-night party.
Unlike Gunter, Aly and Jorge Guinle, Rubirosa was not born into money. His father was a diplomat of the Dominican Republic, posted to France, where young Porfirio went to school. He achieved very little academically but he did acquire savoir faire and made wealthy friends, who hosted him in Biarritz and other playgrounds of the rich. He had found his calling. The challenge was how to fund it.
Back in the Dominican Republic, he met the dictator Rafael Trujillo, who made him a lieutenant of his Presidential Guard in 1931. The following year he married Trujillo’s daughter, Flor de Oro. His relationship with Trujillo defined the rest of his career, and despite a few hiccups, including a divorce from Flor de Oro, the dictator supported Rubirosa with diplomatic assignments and occasional financial help.
Rubi, as he was known, served as a diplomat in Vichy France, Buenos Aires, Rome, Havana and Brussels, as well as his beloved Paris. His second wife was Danielle Darrieux, then the leading film star in France. Over the course of his life, he was romantically linked to hundreds of women, including Dolores Del Rio, Ava Gardner, Kim Novak, Zsa Zsa Gabor, Eartha Kitt, Veronica Lake, Eva Peron, Dorothy Dandridge and, of course, Rita Hayworth.
Rubirosa married two of the richest women in the world, Doris Duke and Barbara Hutton. Duke had inherited a vast tobacco fortune. Barbara Hutton’s inheritance came from a Wall Street brokerage firm, E.F. Hutton, and the Woolworth retail company.
Neither Duke nor Hutton was a great beauty and both appear to have regarded Rubi as a trophy. A friend of Duke’s commented that “he was for pleasure, like a caprice, a whim”. A friend of Hutton’s said that she suggested marriage to Rubi saying “You married Doris, now it’s my turn”.
The two ‘richest girls in the world’ had a kind of frenemy rivalry. Each of them gave Rubirosa a similar wedding ‘dowry’. From Duke, whom he married in 1947, he received $500,000 (about $6 million in today’s money), a stable of polo ponies (he was a keen and competent polo player), several sports cars (he was a keen but untalented race car driver), a converted B25 bomber and a Paris townhouse full of antiques. The marriage lasted less than two years, its end hastened when Doris found him in flagrante delicto with his first wife Flor.
From Hutton, who married him in 1953, he received gifts including another string of polo ponies, another converted B25 - the previous one had crashed - a coffee plantation in his native Dominican Republic and $2.5 million. He was her fifth husband, following two minor princes, the actor Cary Grant, and a Danish Count. She was an emotional and physical wreck when she hooked Rubi. They had no honeymoon and he complained that she stayed in bed all day with windows shut and blinds down. He was bored and soon started to wander. The marriage lasted only 53 days.
How was it that a man with no money of his own was able to attract scores of wealthy, famous or aristocratic women, not to mention waitresses and others whose names will never be known? Undoubtedly, he was a suave and sophisticated suitor, capable of great charm and dramatic romantic gestures – such as wooing Zsa Zsa Gabor by filling her suite at the Plaza Hotel with red roses. But would women who could have any man they desired fall in such numbers for a slick diplomat from a country they probably could not find on the map?
The clue to Porfirio’s extraordinary success with the ladies may lie in the fact that, to this day, the word ‘Rubirosa’ is used to describe the largest peppermills. Waiters at Maxim’s in Paris apparently coined the term, having heard on the grapevine of Porfirio’s gigantic sexual endowment. Doris Duke described it as “the most magnificent penis I had ever seen”. Flor de Oro said she had had difficulty sitting down for a week after her wedding. In 1963, the British journalist Susan Barnes, later the wife of cabinet minister Anthony Crosland, told Vanity Fair of the time she interviewed Rubi in his suite at the Savoy and, on re-emerging from the bathroom, found “a grinning Mr. Rubirosa in his boxer shorts, through which stood a donkey-style member. He threw me onto his unmade bed and a wrestling match ensued as this grotesque thing swung about”. Perhaps because she was able to extract herself, Barnes seems to have made light of this alarming encounter.
No less a literary figure than Truman Capote celebrated Rubi’s member, describing it in his novel Answered Prayers as purported to be eleven inches long and as “thick as a man’s wrist”. It would be a big surprise if Capote was commenting from personal observation, but no surprise at all that he should have taken an interest.
Rubi was also reputed to be priapic and he acquired the nickname ‘Toujours prêt’. ‘Always ready’ is also the motto of the United States Coastguard, although it is fair to assume that it carries a different implication in this context.
Aspiring playboys looked to Porfirio Rubirosa as a model. When Gunter Sachs arrived in Paris in 1957, Rubi and he quickly became friends. Gunter had the money - which Rubi always needed - and Rubi knew all the right people and the best places. Juan Capuro, a wealthy Uruguayan, also became a close friend and follower of Rubi’s lead. He has been described as a Rubirosa clone. And like Rubirosa, he died crashing a fast car, just a year after his mentor.
These were some of the classic playboys - men who either had lots of money or, in Rubi’s case, managed to acquire it - and in all cases they were men who spent heavily on their pleasures. But the word ‘playboy’ soon came to be associated in many - perhaps most - people’s minds with Playboy magazine, which was created for men who could only dream of the kind of lifestyle enjoyed by Howard Hughes, Jorge Guinle, Aly Khan, Rubirosa, Gunter Sachs or Gianni Agnelli.
Playboy magazine was originally going to be called Stag Party. In 1953, Hugh Hefner, the 27 year-old son of conservative, middle class parents, left his copywriting job at Esquire magazine to start his own edgier publication, more focused on the bon vivant lifestyle and, of course, sex. Hefner’s magazine would include nude photos of beautiful women and articles about sex, as well as cars, cocktails and other things geared to men looking for a little escapism in the conservative, conformist 1950s.
The first edition was just about ready to go to print when the publishers of another men’s magazine, Stag, threatened Hefner with a lawsuit to protect their trademark if he went ahead with the name he had chosen. One of Hefner’s investors suggested the name Playboy. His mother had worked for the short-lived Playboy Motor Car Corporation. That company, founded in Buffalo in 1947, had produced a small and sporty convertible with the young man-about-town in mind. The cost was under $1,000, equivalent to little more than $10,000 in today’s money.
Only 99 cars were produced before the company had to close its doors. In a stroke of exceptionally bad luck, the investors took fright after accusations of stock fraud caused a completely different automobile start-up company, Tucker Corporation, to fail. There was no connection between Tucker and Playboy, but that didn’t matter. With its investors jumping ship, Playboy had no choice but to file for bankruptcy and its founder lost everything.
The Playboy car company’s logo featured a top hat, like the Stork Club, along with a pair of white gloves and a cane - the image of a playboy at that time. Hugh Hefner liked the name and he wanted an image of sophistication, but also of something playful and sexy. Hence his Playboy company logo, which soon became one of the most recognizable in the world - a rabbit with a bow tie. The rabbit was suggestive of friskiness, not to say frequent copulation. The bow tie was the successor of the top hat and cane.
The first edition of Playboy magazine went on sale in December 1953 for 50 cents. It had no date on it because Hefner could not be sure there would be a second issue. All the money had been invested in that first issue. He need not have worried. It sold out fast - over 50,000 copies. The reason was that Marilyn Monroe was on the cover and, totally uncovered, inside the magazine.
Monroe was the most famous film star in the world at that time, but the nude photos had been taken four years earlier when she was still relatively unknown and struggling to pay bills. She had been paid $50 for the shoot and the photos had appeared in calendars.
Hefner tracked down the owner of the photos and purchased them for $500. He gave nothing to Marilyn Monroe and did not even inform her that he was publishing them in his magazine. She later claimed that she had had to buy a copy in order to see herself in it. But it was she who had made the first issue a success. Hefner was able to pay back his investors and start work on a second issue. He went on to build a large business. By the 1970s, the magazine commanded a circulation of 7 million. Playboy Enterprises grew to include 40 clubs and casinos in cities in the United States and around the world, where the waitresses - known as Playboy Bunnies - wore lingerie outfits with rabbit ears, cottontails, bow ties and cuffs.
In 1974, Hefner moved to a large house in Los Angeles, which became the ‘Playboy Mansion’. It was known for its lavish parties and for Hefner’s rotating groups of three or four girlfriends at a time. Since his death in 2017 at age 91, several of the women involved with him and with the Playboy company have described a cult-like atmosphere and a culture of exploitation at the mansion.
Multiple women claim to have been drugged and raped there. The current owners of the Playboy brand denounced Hefner ahead of the premiere of a television docuseries Secrets of Playboy early in 2022.
While one can hardly admire the essentially trivial, hedonistic lives of the archetypal playboys of the past, like Rubirosa, Aly Khan or Gunter Sachs, they were at least men who had the charisma to attract, court or marry independently wealthy and powerful women. By contrast, Hefner created a machine for exploiting young girls looking for a break in life. Whatever brand value the word ‘playboy’ may once have had, has now been diminished - its once glitzy image forever tarnished.
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