The 12 Original Playboys of the Jetset Sixties

Part two of five.

As we introduced yesterday, The 12 Original Playboys were a self-proclaimed ‘elite breed of professional pleasure seekers’ who fascinated the world in the 1950’s and ‘60s. They did so with exceptional genes, unparalleled wealth and, as we learn from today’s batch, exquisite style and grace.

Meet Gianni “The Rake of the Riviera” Agnelli, Francisco “Baby” Pignatari, and Alessandro Principe “Dado” Ruspoli, 9th Prince of Cerveteri.

Gianni Agnelli
Gianni Agnelli

Nickname: ”The Rake of the Riviera”
Nationality: Italian
Occupation: CEO, Principal shareholder of Fiat
Wealth: Richest man in modern Italian history. (Controlled 4.4% of Italy’s GDP, 3.1% of its industrial workforce, and 16.5% of its industrial investment in research)
Notable Women: Donna Marella dei principi di Castagneto, Pamela Harriman, Anita Ekberg, Jackie Rogers
Passions: Fashion, sailing, fast cars, skiing, horses
Quotation: ”Miracles can be made, but only by sweating.”
What to learn from Agnelli: Sprezzatura (“making the difficult look easy”). Esquire named Agnelli one of the five best-dressed men in the history of the world. He wore his wristwatch over his cuff, his tie askew and brown hiking boots under a bespoke suit, all of which appeared to be errors, giving the impression he did not care about the way he was dressed.

Francisco R. Pignatari
Francisco R. Pignatari

Francisco R. Pignatari

Nickname: “Baby”
Nationality: Brazilian
Occupation: Metals, President of Laminação Nacional
Wealth: Heir to one of the richest families in Brazil
Notable Women: Marina Parodi Delfino, Inga Lindgren, Dolores De Rio, Selene Walters, Nelita Alves de Lima, Linda Christian, Soraya, ex-Queen of Iran, Vikki Dougan, Tracey Morgan, Melissa Weston, Jorginho Guinle, Zsa Zsa Gabor, Helen and Ann Merrill, Joanna Moore, Karen von Unge, Barbara Cailleux, Jackie Lane, Lucinda Sherill, Susan Cabot, Miiko Taka, Tina Louise, Princess Ira Von Fuerstenberg, Kathy Bonn, Maria Regina Fernandes
Bold Move: After thoroughly enjoying Andy Russell’s crooning in New York, Francisco “Baby” Pignatari sent him a 155-piece silver and 24-carat gold dinner service set which arrived via plane along with two guards.
Passions: Cabaret crawls, fast cars
Age at Death: 61
What to learn from Baby: “Baby never put anything in writing. He’s the only person I know who gives a girl a diamond bracelet without a card. And he only gets about four hours’ sleep a night.” – Richard Gully, social secretary.


Nickname: “Dado,” “World Most Handsome Man”
Nationality: Italian
Occupation: When asked why he never worked a day in his life, Ruspoli replied, “I never had time.”
Wealth: Mother was heiress to one of the largest fortunes in Brazil, died when he was 9.
Notable Women: Francesca dei Baroni Blanc, Nancy de Girard de Charbonnières, Debra Berger, Theresa Patricia Genest
Passions: Opium, world culture, poetry
Age of Death: 81
Quotation: ”I am a tree still full of fruit,” he liked to say, “when all around me I see so many withered vines.”
What to learn from Dado: Dado spent much of his life extolling the virtues of smoking tobacco and opium every day while condemning the use of heroin and cigarettes…

Part One – Death of The Original Playboy: Gunter Sachs, Porfirio Rubirosa
Part Three – The Americans: Howard Hughes, John. F. Kennedy
Part Four – Easy on the Curve: Alfonso de Protago and Prince Aly Khan
Part Five – The Party’s Over: Errol Flynn, Jorge Guinle and Don Carlos de Beistegui y de Yturbe


  • C. Brian Smith