For centuries, society has cheered on men who rack up the greatest number of “conquests” - conquests of women, that is. In some circles, sleeping with thousands of women is ostensibly a badge of accomplishment. Even several popes have bragged about their illicit encounters. Unsurprisingly, many of the biggest playboys in history are also some of the most infamous figures.
When Fidel Castro wasn't palling around with Che Guevara, he was scouring the beaches of Havana for his next “meal.” Pablo Picasso drove two of his lovers to end their own lives. Henry VIII executed two of his wives. But at least one of the men repented shortly before his passing, warning others not to idolize his freewheeling lifestyle.
From Lord Byron to Hugh Hefner, these lotharios were not the greatest male lovers in history - they were historical womanizers who are only now being exposed for their exploits. Weigh in on the sleaziest playboys in history.
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Giacomo Casanova nearly became a priest before he was expelled for sleeping with another student. After leaving the seminary, Casanova devoted himself to seducing women. "Cultivating whatever gave pleasure to my senses was always the chief business of my life," Casanova wrote in his autobiography.
He also admitted to forcing a peasant girl to sleep with him and beating a prostitute when she refused him. He also most likely spread gonorrhea and syphilis to his many partners.
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In 1943, at age 61, Picasso reportedly told his 21-year-old mistress that “women are machines for suffering.” He added, “for me there are only two kinds of women, goddesses and doormats.”
Picasso, who allegedly started visiting brothels at age 13, led at least two of his lovers to end their own lives and two others to suffer mental breakdowns. In the 1930s, Picasso left his first wife, Olga, for his pregnant mistress, but he refused to divorce Olga, preventing her from inheriting any of his wealth. Olga remained married to Picasso until she died of cancer in 1955.
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To woo his second wife, Anne Boleyn, Henry VIII sent her a deer he had killed himself and a note that read, “Hoping that when you eat of it you may think of the hunter.” His tune changed, however, when she failed to bear him any male heirs after they were married. Anne Boleyn and Catherine Howard, Henry's fifth wife, were both executed, while Henry’s desire to divorce his first wife, Catherine of Aragon, led him to split England from the Roman Catholic Church.
He also divorced his fourth wife, Anne of Cleves. His third wife and the only one to produce a surviving male heir, Jane Seymour, died of blood poisoning. His sixth and final wife, Katherine Parr, outlived Henry.
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The Cuban dictator Fidel Castro supposedly slept with 35,000 women in his lifetime. Castro reportedly sent his guards out to the beaches of Havana to recruit beautiful women for him to sleep with.
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Former girlfriend Holly Madison revealed that Hefner ranked every girl who visited the Playboy Mansion and expected his girlfriends to regularly participate in scheduled group encounters. Hefner even bought a burial plot next to that of Marilyn Monroe, whose nude pictures he put on the cover of his magazine without the actress’s consent.
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James Bond creator Ian Fleming spent a great deal of time seducing women. One female friend said of Fleming, “No one I have ever known had sex so much on the brain as Ian.”
Fleming himself once shared his feelings toward women with a friend, claiming that women were like pets or dogs. Incidentally, Fleming left renowned British military academy Sandhurst because he contracted gonorrhea from a prostitute.