Throughout history, many of the biggest womanizers have had dark sides to their charm. In fact, the level of charm you find in so-called playboys can be a sign of a sociopathic disorder. Keep reading for a quick look at the dark side of some of history’s biggest playboys and womanizers, from Casanova and Hugh Hefner to Henry VIII and JFK.

Casanova: From Womanizer to Sexual Abuser

Casanova is such a famous womanizer in history that the word “Casanova” can now mean any one who is quite successful when it comes to the bedroom.

Many people don’t know this, but Casanova was a well-educated man who lived in Venice and took advantage of the relatively relaxed social attitudes of the era. He graduated from the University of Padua with a law degree at only 17.

An adventurer and general hedonist, Casanova enjoyed sexual exploits all over Europe. Thanks to Casanova’s tell-all autobiography, we know a great deal about European social norms in the 1700s. In his autobiography, he refers to more than 120 romantic or sexual encounters with women and girls.

The dark side to Casanova comes from his often violent sexual appetites. Scholars believe that Casanova frequently sexually abused and raped women as well as girls as young as 9. In one disturbing instance, he and seven others abducted and raped a woman. In another, he paid a 16 year old girl’s mother to take her virginity. When the girl refused to have sex with him, he beat her with a broomstick to get his way.

An illustration depicting a young man wearing a red and blue garment. He is standing in an indoor setting, with his face looking directly at the camera. His hair is white and he has facial features that suggest he is in his early twenties. The man's outfit consists of a long-sleeved jacket with buttons down the front, as well as a lace tie around his neck.
Casanova, Illustration

Lord Byron: Literary Celebrity and Serial Cheater

Lord Byron is one of England’s most famous poets from the Romantic era, but did you know that he was also considered a wild man who reveled in sexual pleasure?

Byron truly began embracing the art of seduction as a student at Trinity College, Cambridge. While nowadays we think of actors and athletes as people who can easily convert their fame into sex, it was literary stars like Byron who held this role in the early 1800s.

Byron’s long poem Childe Harold’s Pilgrimage was a huge hit and sparked “Byron-mania,” allowing the poet to turn his literary success into success of the sexual kind. Byron had such scandalous affairs that he had to divorce his first wife and leave England.

Ultimately, he was killed during this exile while fighting for Greek independence at only 36 years old. He left behind his romantic partner, a 22-year-old countess who had left her husband for him. Byron-mania, indeed!

A young man and two young women stand side by side in an outdoor setting. The man is wearing a black suit with a white shirt, and a black tie. His hair is dark and curly. The women are wearing long, light colored sleeveless dresses.
Lord Byron, Illustration

John F. Kennedy (JFK): Did He Indirectly Die from His Affairs?

It’s hard to imagine someone like Barack Obama sleeping around while president. Yet fairly recent examples like Bill Clinton or Donald Trump show how men with power often carry out extramarital sexual exploits.

During his presidency, the public wasn’t really aware of JFK’s wild sexual activity. It only came out after his death in 1963. Speaking of his assassination, some believe his womanizing even partially resulted in his death.

You see, the Secret Service had supposedly become tired of sneaking his lovers in and out of the White House, so they didn’t ride on the side guard of his car the day he was shot and killed in Texas.

While JFK succeeded in many ways during his relatively short tenure as POTUS, he was a flawed person whose playboy infidelities reveal a darker side to his personality.

John F. Kennedy and two women stand in a formal pose, smiling for the camera. John wears a gray blazer with a red and black striped tie, while the women are wearing elegant 1960s style dresses.
John F. Kennedy, Illustration

Henry VIII: Serial Divorcer and Wife Killer

He was Henry the Eighth, and he nearly had eight wives. Many people know Henry VIII today simply due to the tragic story of his many wives. Here’s a quick summary, for those who may be unfamiliar.

Henry wanted to produce a son so that he would have an heir to his throne, but his efforts were unsuccessful. Although the fault likely lay with his health issues, Henry blamed it on the women he was married to.

While Henry may have genuinely loved his first wife, Catherine of Aragon, he created the Church of England just so he could divorce her. His subsequent four wives ended up beheaded, dead from childbirth complications, divorced, and executed.

It was only Catherine Parr, his last wife, who outlived him (by one year).

This portrait depicts king Henry VIII, a man wearing a 16th century-style garment. He is standing in an indoor setting, with the walls and floor of the room painted brown. The man has dark hair and appears to be in his late thirties or early forties. He is wearing a long-sleeved shirt that buttons up at the front, along with white tights and shoes of matching color. On top of this he wears a waistcoat with intricate detailing on it, including embroidery around the edges and pockets as well as decorative buttons down its length. His outfit is completed by a hat which sits atop his head, adding to the overall Tudor era look of his ensemble.
Portrait of Henry VIII, Wikimedia Commons

Hugh Hefner: The OG Playboy Who Drugged and Manipulated His “Girlfriends”

Hugh Hefner is singlehandedly responsible for the popularity of the word “playboy” in the popular imagination, as his Playboy empire is the twentieth century’s most vivid example of a womanizer’s dream.

Due to his hugely popular magazine, which featured nude women, Hefner was able to build up a persona as a playboy. Young and attractive women would stay with him in the infamous Playboy mansion. He would even have multiple girlfriends at once, as seen in the reality TV show The Girls Next Door (2005-2010).

Unfortunately, as is often the case, this womanizer had a dark side. While Hefner proclaimed to be a feminist and about sexual liberation, a recent documentary (Secrets of Playboy) has revealed that he was a predator who would use drugs to control the women around him and take advantage of them sexually.

This photo depicts Hugh Hefner and two blonde women posing for a picture in an indoor setting. They all have bright smiles on their faces, and Hugh is seated in a chair while the two women stand to his sides. All of them are wearing formal clothing, Hugh has on a red robe and black pants, while the women wear red dresses.
Hugh Hefner, Rolling Stone

Charlie Chaplin: A Little Man with a Little Mustache and a Large Ego

Charlie Chaplin is probably the most recognizable and beloved movie star from the silent film era. His slapstick, physical comedy has left an indelible mark in film history, without a doubt.

Unfortunately, there’s a dark side to Charlie Chaplin, who grew up in a troubled household. While he had become one of the most famous men in the world by his mid-20s, Chaplin was only 5’5” and likely exhibited Napoleon syndrome (named after the famous military man we will cover below).

While divorcing his wife, Chaplin met a 12-year-old girl who would eventually become his next wife four years later. Later, Chaplin would marry an 18-year-old when he himself was 54. While this is still fairly common with Hollywood types, it’s not a great look! Many reports suggest that Chaplin was a tyrant on set as a director and also a cruel father to his children.

This image features Charlie Chaplin, a man wearing a black fedora hat, with a white background. He is smiling and has an air of confidence about him. His face is framed by the brim of his hat, which casts shadows on his cheeks and forehead. The man's clothing consists of a dark suit jacket over a light-colored shirt and tie, completing the look with classic style. This portrait captures Charlie Chaplin in all his iconic glory - from the signature bowler hat to the mischievous smile that made him famous around the world.
Charlie Chaplin in costume, enhanced and colorized image

Fidel Castro: The Communist Who Felt Entitled to Sex from Tens of Thousands of Women

Not many people expect to see the name Fidel Castro on a list like this. Ultimately, however, it seems that Castro embraced the “share-the-wealth” policies of communism, as he apparently slept with tens of thousands of women throughout his life.

There is a stereotype in Latin countries about macho men. They are often considered the ideal type of man. They are womanizers, or mujeriegos, and this personality trait often connects to their social standing. As el Presidente, wouldn’t Castro have been expected to reap the benefits of his power and fame?

According to a Vanity Fair article, Castro couldn’t wrap his head around the Monica Lewinsky-Bill Clinton scandal. He considered himself entitled to women, and he couldn’t see how this could be a terrible attitude for a political figure in a position of power.

This image shows a group of people gathered together in an indoor setting. In the center is Fidel Castro, wearing a gray shirt and pants. He is surrounded by four smiling women. He also has a wide smile on his face as he looks out at the women around him.
Fidel Castro surrounded by women, enhanced and colorized image

Napoleon Bonaparte: The Military Master with Mistresses and Unacknowledged Children

Napoleon is well-known today for having governed France in the wake of the French Revolution and for possessing a keen military mind. Apparently, his skill at navigating the battlefield also extended to navigating the bedroom.

Like Casanova, Napoleon had Italian origins, and these impacted his childhood. He was bullied due to his poor French and this, along with his small stature, likely led to his inferiority complex.

Napoleon’s first wife cheated on him, and it was publicized by the British to embarrass him. He himself had mistresses, and he divorced her in search of producing an heir (not unlike Henry VIII).

It is likely Napoleon had multiple illegitimate offspring, most of whom he did not acknowledge or support. This is a common dark side among history’s most prominent womanizers.

This painting depicts a man, Napoleon, and a woman, Josephine. The woman is wearing a white dress with intricate lace detailing, while the man is wearing white pants and a long blue and red jacket. On the floor are papers scattered around their feet, along with what appears to be a vase and other decorative items nearby.
Napoleon and Josephine by Harold Hume Piffard