Initially the term was used in the eighteenth century for boys who performed in the theatre, and later it appears in the 1828 Oxford Dictionary to characterize a person with money who is out to enjoy himself. By the end of the nineteenth century it also implied the connotations of "gambler" and "musician." By 1907, in J. M. Synge’s comedy The Playboy of the Western World, the term had acquired the notion of a womanizer. According to Shawn Levy, the term reached its full meaning in the interwar years and early post WWII years. Postwar intercontinental travel allowed playboys to meet at international nightclubs and famous "playgrounds" such as the Riviera or Palm Beach where they were trailed by papparazzi (immortalized in Fellini's La Dolce Vita) who supplied the tabloids with material to be fed to an eager audience. Their sexual conquests are rich, beautiful, and famous. In 1953, Hugh Hefner caught the wave and created the Playboy magazine.
Porfirio Rubirosa who died in a car crash in 1965 is an example of someone who embodied the playboy lifestyle. The diplomat claimed to have no time to work being busy spending time with women, getting married briefly and in sequence to the two richest women in the world, drinking and gambling with his friends, playing polo, racing cars, and flying his airplane from party to party. He was linked to other famous playboys of his day, Aly Khan, "Baby" Francisco Pignatari, and later, Gunther Sachs, his acolyte, who termed himself a homo ludens.
Other people who adopted the playboy lifestyle included Howard Hughes, Errol Flynn, Conrad “Nicky” Hilton, Fernando Lamas, Imran Khan, Prince Alfonso of Hohenlohe-Langenburg, Gianni Agnelli, Silvio Berlusconi, John F. Kennedy, Alessandro "Dado" Ruspoli, Carlos de Beistegui, Count Theodore Zichy, David Frost, and Bernard Cornfeld.
- "The 12 Original Playboys of the Jetset Sixties". Kempt.com. UrbanDaddy. August 17, 2011. Retrieved 2011-08-24.
- Levy S., p. 117
- Schultz, Ole (February 13, 2003). "Riviera-Nichtstuer - Geschichte der Playboys." (in German). Deutschlandradio Kultur. Retrieved December 20, 2010.
- Levy S., p.117
- Levy S., p. 118
- Zichy on the 'Art & Popular Culture' website
- "When the playboy met the liar". theguardian.co.uk. Theguardian. August 1, 2006. Retrieved 2013-02-05.