10 of the Worst Womanizers in History

10 of the Worst Womanizers in History

D.G. Hewitt - April 10, 2018

Behind every great man, there’s a great woman. Or so the saying goes. However, some of the most famous men in history were never satisfied with one woman. Or even two, or three or four. Some had insatiable appetites, using their fame, wealth, power or even their natural charms to seduce dozens, if not hundreds, of ladies. Sometimes, they were great romantics, or sometimes they were more sinister in their motives. And sometimes their womanizing ways were almost inevitable given their own childhoods and formative years.

Of course, throughout history, countless notable men, especially those in positions of power, have enjoyed playing the field. Stalin and Fidel Castro, for example, both had insatiable sexual appetites though they satisfied themselves more through coercion or fear than through the art of seduction, so such men aren’t featured here. Rather, here are ten of the biggest womanizers in human history, whom women flocked to willingly despite – or perhaps because of – their reputations.

10 of the Worst Womanizers in History
Casanova was such a lothario that his name has become a byword for a womanizer. Biography.com.


Any list of history’s greatest lotharios must surely kick off with the Italian aristocrat who gave his name to men who love women as much as they love adventure. Indeed, though he may not have had as many notches on his bedpost as other womanizers, Casanova has gone down in history as being a great seducer, a man with a huge appetite for the finer things in life. What’s more, his diaries aren’t just kiss-and-tell books. Rather, through his written work, Casanova has helped us gain an understanding of the customs and social norms of 18th century Europe – the naughty tales hidden in them are just a nice bonus for the historian!

So, how was this legendary lover? Giacomo Girolamo Casanova was born in the Republic of Venice in the year 1725. The son of a dancer and an actor, he was actually raised by first his grandmother and then by priests. It was while staying at a religious orders boarding house that he had his sexual awakening at the age of just 11. While not distracted by his female companions, the young Casanova was highly intelligent and relatively diligent. He won a place at the University of Padua to study law and, upon graduation, he started a career in the legal sector.

However, law was not the only thing Casanova was trained in. As a young man, an elderly Venetian senator by the name of Alvise Gasparo Malipiero took him under his wing and taught the younger man all about good food, good wine and the art of seduction. Shockingly, Casanova put what he learned into practice and ended up seducing the object of his mentor’s affections. He was cast out of his native Venice, and so began one of the most colorful lives ever lived. Over the years, Casanova served as a military officer, a spy, and a writer. His many adventures are told in The Story of My Life, written when he was an old man. Around one-third of the huge volume is dedicated to Casanova’s affairs of the heart.

In all, Casanova recalled around 120 flings and affairs. Traveling right across Europe, from Moscow to Madrid, he bedded countesses but also milkmaids, and seduced innocent virginal teens as well as high-class and low-class prostitutes. But, for his fans, Casanova was no cad. Rather, he was a great admirer of women and could even be regarded as an early-day feminist. He made an effort to help out all his lovers, and he loved mental connections as well as physical ones – so much so that he had no fondness for English prostitutes since he could not have a proper conversation with them! Casanova died in 1798, aged 73, but only really became famous with the publication of his memoirs several decades later – and even then, it has been his sexual prowess that has been remembered above all else.

10 of the Worst Womanizers in History
King Charles II’s numerous affairs almost drove England to bankruptcy. Wikipedia.org.

King Charles II

Forget Henry VIII, when it comes to womanizing English kings, Charles II stands head and shoulders above the rest. This was a monarch for whom running the country appeared to be an unwanted distraction. He’d rather have devoted all his time and energy to satisfying his first love – the thrill of the chase. Indeed, while some kings and queens may have been discreet in their liaisons, Charles II was shameless, openly flaunting his affairs and boasting of his prowess in the bed-chamber. So decadent was the monarch that he almost bankrupt the country. In his defense, however, maybe he had good reason to ‘live for the moment’….

Charles II had stressful adolescence, to say the least. In 1649, his father, King Charles I was executed by Oliver Cromwell in London, bringing the bloody English Civil War to an end. Worried that he would be next to feel Cromwell’s wrath, the young man went on the run, heading across the water to France and lying low for a while. Or for 11 years of drinking and womanizing, to be precise. In 1660, England’s experiment with parliamentary rule was over, and the monarchy was back in favor. Charles II was on the throne, and he had a divided country to unite. However, he clearly had other things on his mind.

By all accounts, the court of Charles II was like a 17th century Playboy Mansion. In 1662, Charles II married Catherine of Braganza, a sound political union. However, he chose to watch her state procession through London from the roof of his banqueting house, in the company of one of his favorite mistresses. This was far from the only time the king flaunted his infidelities. In fact, he tasked members of his court to bring him young women – actresses were a particular favorite – and he would usually have around 15 ladies in his harem at any one time. The exact number of lovers he had, and indeed the number of illegitimate children he fathered in his affairs, will never be known.

Charles loved to spoil his mistresses, often buying them apartments and fixing them up with expense accounts, much to the annoyance of Parliament. Given his financial mismanagement, as well as his decadent lifestyle, it’s a miracle that the people didn’t rise up against Charles II. However, he stayed on the throne for 25 years, living the good life. He eventually died in 1685, the morning after a lavish party in which he enjoyed the company of his favorite mistresses – an appropriate end for the ultimate playboy monarch.

10 of the Worst Womanizers in History
Lord Byron’s dashing looks earned him countless admirers and lovers, both male and female. Wikipedia.org.

Lord Byron

George Gordon Byron, better known simply as Lord Byron, was an English politician, nobleman and poet. However, he is now known just as much for his colorful – and often crazy – personal life than he is for his many professional accomplishments. And for good reason. This was a man who had a club foot and was almost always overweight – especially by the standards of 18th century high society – but who was universally adored and took full advantage of his fame to seduce countless men and women. Lord Byron was, as the popular phrase goes, “Mad, bad and dangerous to know“.

A modern-day psychiatrist would have had a field day with Bryon. They’d almost certainly trace his adult behavior back to his childhood. He was born in London in 1788 to Captain John “Mad Jack” Byron and his second wife, Catherine Gordon. Captain Byron was every bit as crazy as his nickname suggests. He was a drinker and a serious womanizer and eventually killed himself by cutting his own throat. His mother, meanwhile, struggled with her weight and depression, as well as from financial difficulties. Being sent away to board at Harrow school would have been a relief for young Bryon, then, especially since it allowed him the chance to enjoy some sexual escapades.

After a few awakenings at Harrow, Bryon went to study at Trinity College, Cambridge. Here, he took a number of lovers, both male and female. However, it was the success of his first literary works which really allowed Bryon to shake off any insecurities he might have had about his weight or club foot and finally start living the playboy lifestyle he enjoyed so much. His poem Childe Harold’s Pilgrimage was a best-seller. London was gripped by ‘Bryon-mania’. Women wanted to be with him, men wanted to be him – so much so that they would copy his hairstyle and surly gaze.

Despite his fame in England, Byron hit the road, traveling extensively through Europe, taking lovers, young and old, male and female, as he went. However, he soon racked up huge debts. Realizing that a good marriage to a wealthy woman could help him, Bryon took Annabella Millbanke as his wife – though not before he embarked on a scandalous affair with his own half-sister. Inevitably, Bryon struggled to settle down, and his numerous infidelities led to his divorce in 1816. Bryon was again forced to leave the country, eventually settling in Italy with his friend and fellow poet Percy Shelley. But he could not stay still for long. In 1823, he accepted an invitation to join the movement for Greek independence. Reluctantly leaving a 22-year-old countess – who had left her own husband for Byron – behind, he headed off to war. Lord Byron was killed in April of 1824, aged just 36. He left behind him not just several volumes of fine poetry, but many hundreds of broken hearts.

10 of the Worst Womanizers in History
Picasso’s insatiable sex drive lasted well into his 70s. New York Times.

Pablo Picasso

Every great artist needs a muse to inspire them, right? Well, in the case of Pablo Picasso, he needed more than one. In fact, over the course of his long, eventful life, the Spaniard took hundreds of lovers and several wives, with many affairs overlapping. For his supporters, such dalliances inspired Picasso in his work. To his critics, however, while he was undoubtedly an artist without peers, as a human being he was seriously flawed, with his womanizing ways causing much grief and heartbreak.

Like with so many serious womanizers, Picasso was introduced to sex from an early age. Born in 1881, he started to frequent brothels in his native Malaga from the age of 13. Shockingly, it was his father who took him to these houses of ill-repute. These early experiences shone through in his first works of art. Many early paintings were practically pornographic and scandalized the deeply Catholic society of the time. Once he moved to Paris at the start of the new century, his talents only grew – as did his insatiable lust.

Throughout his career, Picasso produced around 2,500 works. And it’s estimated he had just as many lovers. By all accounts, Picasso liked his women to be submissive to him, and also to be shorter than him. Some he took as models and lovers for just a day or two, others stayed part of his life for weeks, months or even years. Yes, he married, but any wedding vows didn’t mean much to Picasso. In 1935, he left his first wife, Olga, for his pregnant mistress, Marie-Therese Walter (almost 30 years his junior), though he refused to get divorced as he didn’t want to lose any of his fortunes. Even in old age, he was insatiable. He married again at the age of 79, though even then he would pursue other women in full view of his wife Jacqueline.

However, there was a darker side to Picasso’s fun. According to several histories, his lack of fidelity, or even compassion for those closest to him, caused more than just a few broken hearts. His first wife Olga would eventually drink herself to death as she was unable to cope with Picasso’s refusal to grant her a divorce. Another two of his lovers were driven to mental breakdowns, and he never spoke to two of his four children after their mother published a tell-all memoir about her time with the great artist.

Picasso died in 1973 at the grand old age of 1973. His second wife Jacqueline was by his side. But there was one more twist: A statue of Marie-Therese was placed on top of his grave, a testament to his great love for her. Marie-Therese Walter hanged herself just four years later, while Jacqueline shot herself in 1986, unable to live without the man she had been obsessed with despite his cruel nature and womanizing ways.

10 of the Worst Womanizers in History
Despite being married to one of the most beautiful women in the world, JFK could never stay faithful. Daily Mail.


These days, a President sleeping with a Hollywood superstar behind the back of his beautiful wife would make front-page news right across the world. But American under President Kennedy was a different world. The young, handsome Commander-in-Chief would enjoy countless affairs, including extra-marital dalliances right inside the White House, without a hint of scandal. JFK was adept at cultivating a popular image of a family man, while at the same time being one of the biggest womanizers of his generation.

As is often the case, biographers look to JFK’s formative years when attempting to explain his insatiable – often self-destructive – sex drive. As a young man, John endured several traumas, not least having to deal with serious illness himself and then with the deaths of two of his siblings. But it’s arguably the behavior of his father that really affected the future president’s relationship with women the most. Joe Senior was a serial philanderer, with his unfaithful ways only too obvious to his own wife and children.

So, when JFK got married to the beautiful Jaqueline “Jackie” Bouvier in 1952, it was inevitable he would soon start to stray. And stray he did. Indeed, according to some accounts, the rising politician believed that only casual sex with a chain of lovers could help cure him of his migraines. Like any good politician’s wife of the time, Jackie simply looked the other way, accepting that her husband took lovers on the side, among them A-list celebrities such as Marilyn Monroe and Marlene Dietrich. He also bedded many other actresses, socialites, and once installed in the White House, secretaries and interns too.

The full extent of JFK’s womanizing ways only really came to light after his tragic death in 1963. What’s more, some claim that his insatiable lust helped contribute to his death – albeit indirectly. So tired had the Secret Service become of sneaking mistresses in and out of the Presidential bedroom that they didn’t ride on the side guard of his car on that fateful day in Dallas. However, while he may have kept his liaisons under wraps during his lifetime, these days JFK is widely regarded as a flawed man and is remembered as much for his personal life as for his political career.

10 of the Worst Womanizers in History
He may have been described as “hideously ugly”, but that didn’t hold John Wilkes back. Parliament UK.

John Wilkes

He may be relatively unknown now, but in his day, John Wilkes was the kind of politician journalists – and the public – love: always ready with a witty riposte or quick quote, outspoken and ready to fight for his principles and, perhaps above all, enjoying a very colorful private life. The 18th-century Member of Parliament was a keen womanizer and an advocate of ‘free love’ 200 years before it became a fashionable concept. So, how much do we know about this legendary lothario and his wily ways?

Wilkes was born into relative prosperity in London, 1727. At first, he was educated at home, but then enjoyed a spell of private tutoring followed by a period studying at the University of Leiden in the Netherlands. It might have been here that Wilkes first got a taste of the libertine lifestyle. For, despite getting married to Mary Meade in 1747, he separated just nine years later. Suffice to say, Wilkes made the most of his single status, enjoying the company of countless London socialites and ‘working girls’.

Let’s just say, however, that Wilkes was no dashing, handsome English gentleman. In fact, by all accounts he was very ugly – indeed, he was once called “the ugliest man in all of England”. He himself didn’t deny this. In fact, he embraced it, boasting that he had become adept at seducing women through his character rather than through his looks. Moreover, he claimed that his charms could beat any rival’s looks in the pursuit of a woman. And he was frequently right.

Throughout the 1750s, Wilkes was one of the key members of the Hell Fire Club. The club, which also included among its members the Earl of Sandwich (he of the bready snack) would host regular debauched sex parties in the heart of London. On occasions, Wilkes and his companions would dress up as members of the clergy and frolic with ladies dressed as nuns. Plus, on one occasion, Wilkes even brought a baboon to a party. It was at such a party that Wilkes reportedly made his most famous barbed comment: When the Earl of Sandwich said to him: “Sir, I do not know whether you will die on the gallows or of the pox,” Wilkes replied, “That depends, my lord, on whether I embrace your lordship’s principles or your mistress.” Ouch.

In the end, Wilkes died at a fine age in 1797. By that time, his womanizing ways had become less crazed. Bored by the libertine lifestyle of his youth, and ostracized by polite society for writing an “obscene, pornographic” poem, he devoted himself to politics. He served as Lord Mayor of London and then a magistrate. As well as his womanizing ways and love of a good scandal, Wilkes is remembered as a progressive and fierce defender of personal freedom.

10 of the Worst Womanizers in History
Peter the Great adored his wife, but adored the company of other women just as much. Wikipedia.org.

Peter the Great

Peter the Great ruled over Russia with an iron fist for almost half a decade. Born in 1672, he ascended onto the Romanov throne in 1689 and stayed there until his death in 1725. Undoubtedly, Peter I – the ‘Great’ part was added later – was a fascinating man. At once progressive and enlightened and also autocratic and cruel. He viewed the Russian people as little more than children who needed a heavy hand to keep them in their place. However, his private life, and above all, his unquenchable thirst for female company, show him to have been lonely, even insecure.

As was common for young royals, Peter was married off at the age of just 16. However, he hated his wife Eudoxia. While Peter was bright and inquisitive – indeed, he traveled the world in search of the latest learning – his first wife was boring, argumentative and dumb. She did, however, give Peter three children. Once her duty had been fulfilled, he sent her off to a convent, where she would remain for 30 years until she was finally pardoned and released by her grandson, Peter II.

Peter’s second marriage was an altogether happier union. Indeed, by all accounts, he genuinely adored and respected Tsarina Catherine. He would invite her along on his travels and she would be by his side for all formal occasions. They were together for 23 years, including 13 as man and wife. But this doesn’t mean he was faithful to her. Nobody knows quite how many lovers he had, but it was a lot. Peter slept with Catherine’s ladies-in-waiting, with her friends or, if he got desperate, with prostitutes. There’s even evidence to suggest he slept with a hunchbacked simpleton one time, though he preferred aristocratic ladies.

Though undoubtedly a cad and an unapologetic lothario, Peter made an effort to treat his lovers well. Those that were married would find that their husbands were awarded land or titles, while his favorites would be lavished with gifts. But, as with so many ‘players’, Peter was quite the hypocrite. When he learned that his wife had become close to a male secretary, he had the handsome German aristocrat in question, executed and his head preserved in a jar. The jar was then presented to Catherine, and may even have been placed by her side of the bed – a constant reminder that, while the Tsar could play the field, she was expected to remain loyal at all times.

10 of the Worst Womanizers in History
Don Miguel’s womanizing knew no bounds, until tragedy struck. Wikipedia.org.

Don Miguel de Manara

If you don’t know the story of Don Juan, then you almost certainly know the name. Indeed, it’s become short-hand the world over for a womanizer. The character dreamt up by the Spanish writer Tirso de Molina in the 1630s was certainly a scoundrel. In the famous book, Don Juan uses his wealth and charms to seduce countless women. The father of one of his conquests, a man by the name of Gonzalo, seeks to defend his daughter’s honor. However, Don Juan kills him. He then walks past Gonzalo’s tomb and mockingly asks his statue to dinner. Much to the protagonists’ shock, Gonzalo’s statue comes to life, accepts the dinner invitation and then proceeds to drag Don Juan down into the flames of hell.

The story makes for great reading, but was there a real Don Juan? Almost certainly. According to most experts, Tirso de Molina based his most famous character on a chap by the name of Don Miguel Manara. And this real-life version was every bit the playboy. Born into great wealth in Seville in 1627, he was a carefree youth. Even though he married at an early age, he indulged in countless affairs, picking up women in the ancient, narrow streets of Seville and gaining a reputation as an insatiable lothario.

But wait! As critics of the story point out, the Don Juan book was penned when Miguel was just a child. True. In a nice twist, the history books show that Miguel was an impressionable 14-year-old when he saw a play based on the book performed in his city. Rather than taking it as a warning against promiscuity, he saw it as a lifestyle guide and immediately set about becoming a seducer of women. As the decades and centuries passed, the two stories became so interlinked that Miguel was widely credited with being the original Don Juan.

In real life, Miguel had a rude awakening. His wife died just a few years into their marriage. So struck with grief was he that Miguel turned to religion and devoted himself to caring for the sick and poor. He set up the Brotherhood of the Holy Charity, an organization that still helps people today, and for his work he was made a saint. It’s for this reason that we have a detailed account of his life, including his womanizing youth.

10 of the Worst Womanizers in History
Out of a harem of hundreds of men, Suleiman the Magnificent became infatuated with one. Smithsonian Magazine.

Suleiman I

Suleiman I – otherwise known as Suleiman the Magnificent – ruled over the Ottoman Empire for 35 years. As the Empire’s longest-ruling Sultan, he held absolute power over as many as 25 million people, a power he wasn’t afraid to exert. Under Suleiman I, the Ottomans became a serious world force, conquering several strongholds of Christianity and becoming highly economically powerful. And the Sultan’s lust for women was almost as strong as his drive for territory and wealth. Like many eastern rulers of the time, he kept a harem and fully enjoyed the benefits that came with his unique position.

Born in 1494, Suleiman was schooled in Constantinople (modern-day Istanbul), and was, by all accounts, a bright and educated young man. So, when his father, Selim I, died in 1520, he was ready to take control of the Empire, despite being aged just 25. Under his enlightened rule, the Ottoman Empire enjoyed a golden age of the arts, with its leader, a talented poet himself, promoting the development of art, literature and architecture. At the same time, Suleiman was also responsible for overseeing notable changes in the education, legal and taxation systems, all helping his Empire flourish. But, what really set the leader apart was his attitude to his lovers.

Of course, having a harem of beautiful women was not unique to Suleiman. He literally had hundreds of young women to choose from, often picking one just for an afternoon or night. Some, however, became his favorites and so, as well as having bedded hundreds of lovers, he also had many children with them, only some of them officially recognized. Though the exact number of women he slept with will never be known, Suleiman definitely took full advantage of his position and became one of the biggest lotharios of the age.

One woman really captured the Sultan’s heart, however. Hurrem, a slave girl with Crimean roots, started out as just another girl in Suleiman’s harem. However, he became infatuated with her and he soon took her as a favorite – a major breach of tradition and protocol. Rather than having to leave court when her children came of age, as was tradition, Harem stayed by Suleiman’s side until her death in 1558, though, of course, her husband continued to enjoy liaisons on the side for all this time. Suleiman himself died in 1566, aged 71, leaving behind a huge empire and an equally sizable harem of frustrated young ladies.

10 of the Worst Womanizers in History
Was this Maharajah the kinkiest ruler India has ever known? Geo.de.

Maharajah Bhupinder Singh Patiala

During the years of British Imperial rule, India was divided up into 562 distinct states, each with their own Maharajah, or ruler. Unsurprisingly, these rulers were a diverse bunch Some were diligent administrators, fair in their methods, while others were incompetent or just downright cruel. Some were modest, while others took full advantage of their positions and enriched themselves at the people’s expense. And some, well, some were just plain kinky, just like the Maharajah Bhupinder Singh Patiala.

Born in 1891 in the state of Patiala, Bhupinder was crowned at the age of just nine following the sudden death of his father. A council ruled in his place until he reached the age of 18, and then he became the youngest Maharajah in India. His ascent was rapid and remarkable. He served with distinction – albeit away from the frontlines – in the First World War, and then went on to assume several key roles within the Raj. With these positions came great wealth, and Bhupinder wasn’t shy about flaunting it.

His banquets were legendary and his appetite was huge. It wasn’t just food he craved in abundance, however. The Maharajah had an insatiable sex drive. He kept a harem of around 500 women, constantly updating its personnel and even transforming individual girls with the help of hairdressers, beauticians and even plastic surgeons. It’s said that Bhupinder followed the London fashion scene avidly and liked to model his harem on the latest trends. His modeled women would be tasked with serving him and his friends in regular, drunken orgies, and, by many accounts, he fathered as many as 88 children through his various liaisons.

The Maharajah’s lust didn’t really slow with age, though he increasingly needed the help of natural aphrodisiacs to perform. He died in 1938 at the age of just 46. The cause of death? According to some observers, Bhupinder simply became bored and lost the will to live, the company of women no longer enough to keep him excited.


Where did we find this stuff? Here are our sources:

The Culture Trip – Does Fidel Castro Really Have Hundreds of Children?

“Who was Casanova?” Walks of Italy

Italy Magazine – The Adventurous Life of History’s Most Famous Lover, Casanova

The Guardian – Enlightenment On Casanova’s Sexual Preferences

Zocalo Public Square – Casanova Was More Than A Good Lover

“The merry monarch and his mistresses; was sex for Charles II a dangerous distraction?” Matthew Dennison, The Spectator, January 2015.

“Lord Byron, 19th-century bad boy”. Clara Drummond, The British Library, May 2014.

Factinate – Debauched Facts About Lord Byron

New York Times – I Love Not Woman the Less, but Man More

Wordsworth – Byron And His Women: Mad, Bad And Very Dangerous To Know

“All the president’s women”. Sara Stewart, New York Post, November 2013.

Cheat sheet – Did Marilyn Monroe Really Have An Affair With JFK?

“John Wilkes Expelled from the House of Commons”. Richard Cavendish, History Today, January 2014.

Standard – Picasso Was An Artistic Genius But He Was Also A Bullying Womanizer

Arthive – Love Story in Paintings: Pablo Picasso and Olga Khoklova

“Torture, castration, rampant sex, murders galore and dwarf tossing. Were Russia’s Tsars the nastiest royals in history?” Roger Lewis, The Daily Mail, January 2016.

“Steamy Turkish soap opera about Sultan and his harem makes MP’s blood boil”. Alexander Christie-Miller, The Times, December 2012.

“The Pleasure Pursuits of Princes”. B.S. Goraya, Punjabi Monitor.

Vanity Fair – It Happened At The Hôtel Du Cap