Weird History
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13 Suave Playboys From Throughout History Who Are Actually Total Scumbags

Updated September 5, 2019 6.7k votes 1.2k voters 54.3k views13 items

List RulesVote up the “charismatic” and “charming” historical figures who were, in fact, cheap manipulators obsessed with sexual conquest.

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.

  • Photo: Fortheloveofknowledge / Wikimedia Commons / CC BY-SA 4.0

    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.

    • Age: Dec. at 56 (1908-1964)
    • Birthplace: Mayfair, London, London, England
    • Profession: Journalist, Novelist, Author, Writer
  • Hugh Hefner, the creator of Playboy and "the idol of teenage boys of all ages," was frequently accused of mistreating women and plying them with drugs so that they would sleep with him.

    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.

    • Age: Dec. at 91 (1926-2017)
    • Birthplace: Chicago, Illinois, United States of America
    • Alternative Name: Hugh Hefner, Hugh Heffner
    • Profession: Editor, Publisher, Businessperson, Journalist, Entrepreneur
  • 7

    Charles II Tried To Employ His Mistress As His Wife's Personal Servant

    Historian Ronald Hutton has dubbed Charles II the “playboy monarch” because he prioritized “the pursuit of pleasure above the more earnest, sober, or martial virtues.” Charles, who took the throne of England after his father was executed by Parliament, "fathered 14 illegitimate children by seven mistresses."

    As a newlywed, he tried to force his wife, Catherine, to accept his mistress as her lady of the bedchamber. She refused, angering Charles substantially. 

    • Age: Dec. at 54 (1630-1685)
    • Birthplace: St James's Palace, London, England
  • Photo: William & Daniel Downey / Wikimedia Commons / Public Domain

    Edward VII Reserved A Pew For His Mistresses At His Coronation

    This English monarch, also known by the nickname “Edward the Caresser,” had a bevy of royal mistresses. He even designated a special pew in Westminster Abbey for “the king’s special ladies” during his 1901 coronation.

    His partners included Winston Churchill’s mother, French actress Sarah Bernhardt, as well as numerous ladies of the evening. Edward even had his own personal chair in a French bordello. His very last mistress, Alice Keppel, was the great-grandmother of modern-day Prince Charles' second wife, Camilla, Duchess of Cornwall. 

    • Age: Dec. at 68 (1841-1910)
    • Birthplace: Buckingham Palace, London, England