In his memoir Don't Mind If I Do, the Hollywood playboy emeritus George Hamilton, now a ripe 72, provided some tips he learnt over the years for attracting the most gorgeous women in the world, including the hardly press-shy Liz Taylor. "A world-class playboy once told me that the key to mesmerising women is to listen to them and look deeply into their eyes. It was a lesson I've never forgotten… My father also had advice for me. It was always important, he told me, to be a ladies' man and a man's man."

"The playboys always married for a time," says Dana Thomas, a longtime Saint-Tropez vacationer, and the author of Deluxe: How Luxury Lost Its Luster. "They were hopeless romantics after all. It just never lasted because they all had wandering eyes." (Rubirosa was married five times, Robert Evans, the American film producer, seven.)

Their fables entered the zeitgeist in the form of pop-culture swordsmen like Thomas Crown, Simon Templar, John Steed of The Avengers and, most famously, James Bond (played for a while by one-time Gstaad resident Roger Moore). "Why is this bunch of endlessly naff, morally dubious, sun-damaged sex addicts so beloved by the media?" moaned The Guardian recently. Well, because they were beloved by so many men who wanted to be them and women who wanted to be with them.

Today we are left not with real playboys but with synthetic playboy nostalgia. There is Mad Men and its paler imitators, such as Pan Am. Hugh Hefner, America's home-grown playboy, is a husk of his former self, celebrating being ditched at the altar on the cover of his own magazine. Perhaps the phoniest version of the jet-setting "good life" appears in Sean "Diddy" Combs's television ads for his Sean John I Am King cologne. Diddy rides a jet ski in a full tux, arrives at a helipad armed with supermodels Bar Refaeli and Ana Paula Araújo at his side, and strides through the Mediterranean in his black tie. If he saw it, Sachs, the impeccably dressed, tousle-haired heir to Germany's Opel automobile dynasty, might shoot himself all over again. In his day, a playboy didn't shout he was a "playah" he just… was. What the deuce did he care if anyone else knew it?

Some fabled playboys were born to the manor, and provided with hefty trust funds, but made something of it. As a young man, the Italian Casanova Agnelli, the heir to the Fiat fortune and one-time lover of the screen goddess Anita Ekberg, was provided a faux title at the auto company. As vice president of nothing, he was told by his grandfather to "have a fling [at the job] for a few years. Get it out of your system." His allowance was $1 million per year. After buying a 28-room villa on the Côte d'Azur (as well as playboy pads in Manhattan and St Moritz), becoming a Formula One race-car driver and ultimately smashing his Ferrari going 140mph above Monte Carlo (breaking his leg in six places), Agnelli grew up and "stopped playing and started thinking". Under his run as the company president, he saved the beleaguered Fiat from going the way of the Edsel. Agnelli lived to a respectable 81.

Some had real life thrust upon them. Roman Polanski, Helmut Newton, Kosinski and the composer Serge Gainsbourg (subject of the new bio-picture Gainsbourg: A Heroic Life) survived Nazi and wartime threats, poverty or family tragedy, and still won fame and fortune.

Evans, the Hollywood producer of such classics as Chinatown and The Godfather, was "discovered" tanning by the pool at the Beverly Hills Hotel. When his acting career proved fatal, he turned to movie producing, and the ladies followed. His father was a dentist.

The message such men sent out was: This could happen to you. Even the talented Mr Ripleys of their day, the skilful gold diggers, proved to be loyal friends, generous hosts, discreet lovers and, well, just too damned much fun not to invite to the party. Take Rubirosa, who wed two of the richest women in the world, Doris Duke and Barbara Hutton, helping to support his race cars and polo ponies, while befriending his country's president, who provided him with diplomat-in-residence titles and salaries. Men and women alike adulated him, enjoying his "ride" in the sidecar, regaling in his getting away with it all.

Charm, 50 years ago, went a long way. After a besotted all-nighter with the Dominican polo player and race-car driver, Sammy Davis Jr ran into the dapper Don Juan at lunch sitting at a bar. "Rubi", as he was nicknamed, was dressed to the nines, drinking a Ramos gin fizz.

The Rat Packer asked him how he kept going. "Your profession is being an entertainer," said Rubirosa. "Mine is being a playboy."

How couldn't you like a guy like that, a throwback to Bogie in Casablanca, a ladies' man and a man's man? Rubirosa, by the way, exited the scene in 1965 in true playboy style, wrapping his Ferrari around a tree just a day after his racing team won the Coupe de France polo cup and celebrating all night at a Paris nightclub. He was 56.

According to Venezuelan-born Reinaldo Herrera, Carolina Herrera's husband and heir to his family's art-and-land-owning fortune, real playboys, "an unflattering term to be called in that day", "were gentlemen, and often sportsmen". Herrera, once an accomplished horseman, now a Vanity Fair contributing editor, adds: "They were interesting to be around. They worked but played well and lived well. They didn't buy $10,000 bottles of champagne to impress a girl or their friends. They were brought up with an instinctive sense of obligation."

"The word 'millionaire' was like the clap, you didn't talk about it," says Evans, who at 81 still counts in his intimate circle playboys such as Jack Nicholson, Roman Polanski and Warren Beatty. "When money is everything, charm goes out the window." Evans differentiates between style, a good thing, and fashion, a superficial thing. "Style preceded fashion for these guys." Newton, the photographer who died in a 2004 car crash by the driveway of the Chateau Marmont hotel, in Los Angeles, was to the film producer "the epitome of style. He was the only person you couldn't officially invite to a party because then too many people would try to crash it. He was that much of a wonderful charmer."

Saint-Tropez acts as a bellwether of what's been lost. It's now all about alcohol-brand-and-celebrity-endorsed private parties, pop-up clubs and techno-Gaga spectacle and whirling choppers hitting the Riviera with the subtlety of a Transformers movie. Baggy shorts and backward baseball caps are the uniform worn by the new players, even at once-chic seaside spots like Club 55 and La Voile Rouge. This summer, the Facebook co-founder Eduardo Saverin stayed in an $8,000-per-night suite at the Hotel Byblos and ran up a $50,000 bar tab entertaining a flock of models.

"I don't go to Saint-Tropez anymore," says Evans, who spent more than a decade hitting the French Riviera and staying at the once discreetly chic Hôtel du Cap. Evans says that the problem with the new-money players is that they're money-smart but culturally anaemic. The 10-digit successes have come so fast for them that there's been no time and, for most of them, no inclination to pursue character-broadening hobbies like lepidoptery or oenology, or interests in Flemish paintings, Gregorian literature, the opera, learning new languages. No time to break Everest records for the Explorers Club or hunt black rhinos in Tanzania.

Have pity on the nouveau-riche playboys, for they know not what they do.

Reprinted in SEVEN by permission of the Wall Street Journal Europe, Copyright © 2011 Dow Jones & Company, Inc. All Rights Reserved Worldwide

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