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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.
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Those specific ideas about courtship, intimacy, and romance
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have shifted a lot across the ages. History is full of figures who are celebrated
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for their ability to spit incredible game. These were men who seduced and satisfied dozens, hundreds
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or even thousands of women. And their illicit encounters became the subject of legend
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Some of their names, such as the famed lover Casanova, even became shorthand for a dashing romantic gentleman
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The thing is, some of them were really big jerks. Today on Weird History, we're looking at some famous historical playboys who were actually total scoundrels
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Okay, time to rock the cradle of love. The real Giacomo Girolamo Casanova was a writer and adventurer who lived in Venice in the mid-18th century
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one of the last centuries in which you could claim adventurer as a profession
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Everything we know about Casanova's life should be taken with the mightiest grain of salt
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because it all comes from his own autobiography, titled Histoire de ma vie, or Story of my Life
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In his stories, many of Casanova's tales of seduction take on a similar pattern
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He meets a beautiful young woman in distress, typically trapped in a violent or unfortunate situation with another man
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He helps her to break free. She shows her gratitude by allowing Casanova to seduce her
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And finally, aboard, Casanova decides to exit the scene gracefully by pairing the damsel off
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with another suitor. Casanova and his romantic exploits were well known in his own time
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but shifting moral and social standards over the last several hundred years have made many of the
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tales seem less charmingly caddish and more predatory in nature, perhaps zeroing in on
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vulnerable women in difficult circumstances and using their desperation to knock some boots
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The memoirs are also filled with some unpleasant tales by just about any standard. At one point
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Casanova admits to forcing a peasant girl to sleep with him, and in another tale, he beats a
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prostitute after she refuses his advances. He also admits in the memoirs to suffering from several
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bouts of painful gonorrhea, which of course he may have been spreading around the European continent
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like confetti at a New Year's Eve party. However, modern researchers failed to detect any microbial evidence
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on the actual handwritten journals themselves. And they were really looking. In addition to being a legendary artist
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for most of the 20th century, Spanish painter Pablo Picasso was also renowned
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as a great lover of many women. He would immortalize the subjects of his romantic escapades on canvas
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as great works of art. And as far as wooing the ladies
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that's a pretty good move. However, Picasso's mistreatment of the women in his life started coming to light after his granddaughter Marina Picasso chronicled his abusive and cruel relationships with his family in a 2000 memoir According to the memoir Picasso
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started frequenting brothels at age 13, triggering an insatiable sexual appetite that would plague him throughout the rest of his life
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And Picasso's relationship with Fernand Olivier, who became an early artistic muse for the painter
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was marked by bouts of insane jealousy. Picasso would reportedly lock Olivier in their studio
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and leave her alone for hours. His romantic relationship with his first wife
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Ukrainian-Russian ballet dancer Olga Kokolova, effectively ended in 1935 after Picasso got another woman pregnant
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Valentine's Day was presumably pretty awkward that year. Nonetheless, Picasso refused to grant his wife a divorce
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She remained legally married to him until she died of cancer in 1955
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As if that weren't punishment enough for the crime of being his wife, he'd later depict Kokolova in paintings as a horse being gored by a mythological minotaur
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representing the artist himself. Picasso was undeniably a master painter, but that's the kind of artwork that typically ends with a parent-teacher conference
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The English King Charles II was dubbed the Playboy Monarch because he prioritized the pursuit of personal pleasure over any sense of duty to his country
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He's the kind of king that wears sunglasses to court. Following the 1649 execution of his father, Charles I
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and the ensuing 11-year English Commonwealth led by Oliver Cromwell, Charles took the throne in 1660, functionally closing out the English Civil War
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Over the course of his reign, he'd father 14 illegitimate children by seven different mistresses
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which is a whole lot of birthday cards to remember to send. But his idea of courtship wasn't all relatively low-cost poetry readings and walks around the garden
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Charles's seemingly endless string of romances and affairs, and the lavish spending that
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came with them, nearly bled the English treasury dry and were blamed for a number of humiliating
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defeats on the battlefield. One mistress, Barbara Villers, the Countess of Castlemaine, was particularly careless with money
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She lived in a palatial estate, demanded a constant influx of expensive gifts
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received a £25,000 income each year, and would rack up extravagant charges
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One evening, she reportedly lost £25,000 playing cards and sent Charles the tab
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Though the king was granted an annual income of £1.2 million in 17th century money
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which in today's dollars is a whole lot of dough, that salary proved to be totally insufficient to satisfy his many women and their many purchases
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Parliament was forced to institute unpopular new measures and taxes in order to make up for
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the shortfall. Courtier John Evelyn commented that Charles would have been an excellent king
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in fact if he had been less addicted to women 19th century British King Edward VII nicknamed Edward the Caresser due to his favorite pastime of wooing new lovers was also notorious for stepping out on his wife
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He went so far as to designate a special pew in Westminster Abbey for his mistresses to observe
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his 1901 coronation. That's bold, even for a king. Among King Edward's most famous conquests
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were the French actress Sarah Bernhardt and the American-born British socialite Jenny Spencer Jerome
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who would go on to become the mother of future Prime Minister Winston Churchill
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Edward's final mistress was Alice Keppel, the great-grandmother of present-day King Charles' wife Camilla, Duchess of Cornwall
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And old Chuck may not have fallen far from the tree, as his infidelity is often blamed for the end of his storybook marriage to Princess Diana
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In addition to his social and political adventures, Cuban revolutionary and dictator Fidel Castro
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was also one of the most infamous womanizers of all time, reportedly betting over 35,000
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women in his day, which doesn't seem mathematically possible. But hey, the bearded look was in
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According to one former underling, Castro slept with at least two women each day for
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a period of more than four decades. Oddly, Castro's encounters tended to coincide with mealtimes
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He's said to have had a woman for lunch, another with supper, and sometimes would ask for an additional companion with breakfast
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It is the most important meal of the day. In a 1993 Vanity Fair article, Castro refers to his offspring as numerous enough to consider a tribe
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Reporter Ann Luzi Bardock also said she was unable to explain the Monica Lewinsky scandal of Bill Clinton's presidency to Castro
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Castro didn't see the problem and believed that Clinton's relationship with an intern
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was a sign of his effectiveness as a leader. But while some of his behavior could almost be considered charmingly caddish
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there was a dark side to Castro's sexual appetite. Bardock also reported that she personally knew girls as young as 15 and 16 who had slept with Castro
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And some later accounts from the Miami Herald and New York Post even linked Castro with notorious human trafficker Jeffrey Epstein
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Like Castro, Playboy founder Hugh Hefner was something of a counterculture icon
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whose reputation was later tainted by stories of unpleasant and abusive behavior
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Although in fairness, Hef never led a repressive regime that took control of an entire nation
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He mostly hung out in his backyard. At the height of Playboy magazine's success and cultural cachet
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Hefner became the avatar of the ideal Playboy, a man who partied every night with the world's most beautiful women
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But by the publisher's autumn years, stories about his inappropriate and abusive behavior
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have become all too common Hefner has been accused by multiple people of assaulting models who were staying in the Playboy mansion sometimes plying them with drugs to render them unable to consent Hefner was also
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later accused of treating employees at his once-popular Playboy nightclubs essentially as
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sex workers, encouraging them to mingle with regulars and covering up assaults perpetrated
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by VIP customers. Friends of former Playboy bunny Adrian Pollack, who succumbed to a Quaalude
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overdose in 1973, later accused Hefner of employing her and other models as low-level
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drug traffickers, serving VIP guests at Playboy clubs and mansion parties. And that's honestly just the tip of the iceberg, if that iceberg were a smoking jacket and
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probably a hairpiece. There are so many troubling allegations surrounding Hefner that Playboy released a statement
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distancing the publication from him in 2022 that read, Today's Playboy is not Hugh Hefner's Playboy
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James Bond ranks among the most seductive fictional characters of all time
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so it's only reasonable that his creator, author Ian Fleming, had a long line of romantic conquests
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And when you consider that Fleming was himself a former intelligence officer during the Second
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World War, all the pieces of the puzzle begin to fall in place. They do say write what you know
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One lady friend of Fleming's once commented, no one I have ever known had sex so much on the brain as Ian
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That's not exactly hard to believe. He did create a character named Galore
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Not your best choice, Ian. Fleming's stories sometimes contained a dismissive and even misogynist view of women
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and his personal view may have been even more extreme. In one letter to a friend, Fleming explained that he grew quickly bored of relationships
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and compared women to pets or dogs. 007 is way more debonair than that
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Another icon of mid-20th century pop culture, actor and singer Bing Crosby's voice
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is forever associated with the Christmas holiday. The crooner behind White Christmas
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The Little Drummer Boy, and many more classic numbers had a reputation in his own day as a great lover
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But the truth is darker. FBI records reveal that, like his fellow singer Frank Sinatra
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Crosby had a number of connections to organized crime And struggled with addictions to alcohol and gambling
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Who knew crooners were so hardcore? Crosby ultimately left behind two marriages
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And seven kids to pursue a string of affairs With several of his co-stars
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Sinatra, for his part, was also no angel Old Blue Eyes left a long list of ex-wives
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And jilted former lovers in his wake And was notorious for hitting on showgirls
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And masseuses backstage in Vegas and elsewhere Sinatra's third wife, Mia Farrow, was just 21 when they got married
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five years younger than Sinatra's own daughter, more like old guys and dolls
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The marriage barely lasted two years, but Sinatra and Farrow remained close for the rest of his life