15 Famous Serial Cheaters In History

The things about cheating is that it is not just a mistake, it's a choice and, unfortunately, it's a choice that many people make a lot. We all know that being cheated on is one of the worst things that can happen to a person but whenever the news gets out about a scandalous affair between famous people, it's really hard to not pay attention. Let's be honest, we all want to know the juicy details about scandalous Hollywood hookups. Hollywood may be known for its famous cases of infidelity but the truth is that all of history is littered with stories of famous adulterers.

Pretty much everyone is familiar with the famous cheating scandals of Tiger Woods, John F. Kennedy, Jesse James, Hugh Grant, and Bill Clinton but it's not just men, there are plenty of women who have cheated too such as Claire Danes, Kristen Stewart, Kim Kardashian, Meg Ryan, and Sienna Miller. It doesn't matter if you're the President of the United States or the star of You've Got Mail, being unfaithful is a hard thing for people to forgive. Among these famous adulterers of history are queens, pop stars, painters, presidents, writers, and actresses and it does not stop there. What sets the famous cheaters on this list apart is that they were either caught or admitted to cheating multiple times. These are some of most famous people in history, all of which were serial cheaters.

15 Cleopatra

via Pinterest

Let's start by going all the way back to 44 B.C. when Cleopatra was the queen of ancient Egypt. She was known for being a beautiful, confident, and wise ruler who was involved in a tragic love affair with the Roman general Marc Antony. However, she was also romantically involved with other men besides the general. When Cleopatra first came to power at 18, she was required to marry her brother, Ptolemy XIII, because a queen had to be led by a king. When she was thrown out of Egypt by her brother, she met Julius Caesar and they became entwined in a love affair though it was mostly just a political agenda on both parts. She eventually met Marc Antony and the two were married. Basically, Cleopatra cheated on her husband multiple times with Marc Antony and Julius Caesar but her husband was also her brother so it's a forgivable offense.

14 Ashton Kutcher

via Fox News

Now let's fast forward in time to another famous love affair of ancient history--Ashton Kutcher and Demi Moore. Throughout their relationship there were many rumors of Kutcher cheating on Moore with multiple women and now that the dust has settled, we know that quite a few of the rumors were actually true. Many women have come forward to say that they spent the night with Kutcher while he was still married to Moore including Scott Eastwood's then-girlfriend Sara Leal which Eastwood also confirmed. In a recent interview, Eastwood said that Kutcher hooked up with Leal and another young woman who was dating one of his friends at the time, proving once and for all that Kutcher was, at one point, a total scumbag and a serial cheater. Though he and his current wife Mia Kunis seem blissfully in love, we hope for her sake that he has changed his ways for good.

13 Madonna

via The Sun

The dating history of Madonna is long and legendary and the list includes Dennis Rodman, Warren Beatty, Antonio Banderas, Lenny Kravitz, Vanilla Ice, Michael Jackson, Willem Defoe, Guy Ritchie, Alex Rodriguez, and Sean Penn. There have been cheating rumors about Madonna for decades throughout her numerous relationships and, let's be honest, there was bound to be some overlap. Her most notorious cheating scandal was the one between her and A-Rod (one of the only celebs whose dating history may actually be longer than Madonna's) which allegedly broke up her marriage with Guy Ritchie. She also dated John F. Kennedy, Jr. while she was still married to Penn (they were separated at the time) but it's hard to feel sorry for Penn who once tied Madonna to a chair and tortured her for hours before she was able to escape. Never forget.

12 Ernest Hemingway

via The Telegraph

He may have been one of the greatest writers of the 20th century but Ernest Hemingway was definitely not the ideal husband or lover. He was a heavy drinker, volatile, physically abusive, and misogynistic. Basically, not a great guy. Over the course of his life, Hemingway had four wives and countless mistresses and often times, his wife and his mistress were forced to interact with each other. Why did they put up with this? Well, he was very charismatic, charming, and handsome which explains why so many women wanted to get it on with the author of The Old Man and the Sea. It would appear that while he showed a soft and romantic side of himself to his wives and mistresses, it was his obsession with his own masculinity that seemed to require him to never be without a woman and it was his goal to seduce every woman he desired even though he saw them as inferior. It's safe to say that Hemingway was definitely not a feminist.

11 Pablo Picasso

via Mashable

The women in Pablo Picasso's life were very often his muses and it all started with Fernande Oliver who he painted during his Rose Period and had a relationship for seven years. When Oliver left, he then fell in love with a woman named Eva Gouel who soon became sick and died an early death. Picasso claimed to have loved Gouel but he was in a relationship with Gaby Lesinasse while she was ill. He married ballerina Olga Khokhlova and while he was married, he had a mistress named Marie-Thérèse Walter who he kept secret...at least until she became pregnant with Picasso's child. Picasso and Khokhlova separated but never divorced because he didn't want his wife to receive half of his wealth. He had a relationship with Françoise Gilot who eventually left because of his abusive nature but while they were still together, he had an affair with 17-year-old Genevieve Laporte (he was 70 at the time). Great painter but not a great guy.

10 Whoopi Goldberg

via Ranker

While Whoopi Goldberg was busy EGOTing, she was also busy with her love life. Goldberg has admitted to cheating multiple times in her life. She admitted, "Yes, I screwed around. Yes, while I was married. I did it five or six times, I did those mistakes." Whether she meant five or six times with one guy or with five or six separate guys, we'll never know but it doesn't matter either way--cheating is cheating. Goldberg has even said on The View that she believed that married men are "fair game" saying, "I believe if a guy allows you to come on to him or you discover he's married and you say no, and he says no no it's ok, I'm not with my wife then he's fair game." Maybe for you Whoopi, but maybe not for the rest of us. Cheating is cheating, no matter what.

9 Frida Kahlo


This famous painter is known for her eyebrows and her red hot love affairs. Frida Kahlo was married to Diego Rivera for ten years but their marriage was riddled with affairs on both sides. One of her affairs was with Leon Trotsky and another was with Heinz Berggruen who was introduced to Kahlo by her husband before they ran off together for a month-long affair in New York. She eventually returned to her husband and never spoke to Berggruen again. She also had relationships with poets André Breton and Isamu Noguchi. But she did not just have affairs with men, Kahlo was also romantically entangled with famous women as well such as painter Georgia O’Keefe, American actress Paulette Goddard, and Mexican actress Dolores del Río. She also had a famous fling with Josephine Baker who also swang both ways. Though she only lived to be 47, she kept herself pretty busy with her beautiful works of art and her long list of lovers.

8 Marilyn Monroe

via Dallas News

Marilyn Monroe had many marriages (not as many as Elizabeth Taylor though) and many love affairs. Her most famous affair was with President John F. Kennedy which may not have even happened though many believe that it did. However, there are many stories of Monroe cheating on her first husband with executives and producers in order to further her career which is something many aspiring actresses were pressured into doing so this rumor probably isn't far from the truth. If her many biographies are to be believed, she had affairs during all three of her marriages with celebrities such as Marlon Brando, Frank Sinatra, and even Joan Crawford. These allegations are most likely untrue but Monroe did have a habit of never being without a man and said of her many relationships that she couldn't stand to be alone but she also couldn't stand to being in a relationship either.

7 Albert Einstein

via Pinterest

Albert Einstein may have been smart but his smarts couldn't keep him from cheating. He and his first wife, Mileva Maric, were married in 1903 and he was cheating with many women throughout the marriage. Maric and Einstein were divorced in 1919 and just a few weeks later, Einstein married his second wife...who also happened to be his first cousin. Albert and Elsa had begun an affair in 1912 while he was married to Maric but Elsa was just one of many women. Einstein's second marriage did nothing to stop his adulterous ways and while he was discovering the theory of relativity, he was having affairs all over town. He had affairs over the course of his marriage with Elsa with women named Estella, Margarete, Ethelle and two women who were both named Toni. He may have been a genius when it came to physics but he wasn't very smart when it came to marriage.

6 Kris Jenner

via Mix 104.1

Matriarch of the Kardashians and self-proclaimed "momager", Kris Jenner has been pretty upfront about her affairs. In her book Kris Jenner and All Things Kardashian, she wrote about an affair while she was married to Robert Kardashian. She described the man who she called Ryan as a producer who she met at a party and that she now regrets the affair. Former soccer player, Todd Waterman has since stepped forward to confirm that he was the man that she had an affair with. There have also been rumors of Jenner having romantic relationships with other men such as O.J. Simpson and her daughter Kourtney's ex-husband Scott Disick but these rumors are not likely to be true. She was also accused of cheating on Caitlyn Jenner (formerly Bruce Jenner) with Waterman again years after their first fling. We may never know for sure since gossip mags are not the most reliable sources of information.

5 William Shakespeare

via Youtube

Though he wrote dozens of famous plays, much of William Shakespeare’s actual life is a mystery. In the film Shakespeare in Love, the playwright is depicted as having an affair with an actress while he was still married but how much of that is actually true? He was married to Anne Hathaway after he had gotten her pregnant and we know that he was probably having an affair with a woman known as the ‘Dark Lady’ which he wrote about in his sonnets. "The Dark Lady" may have been the poet, Emilia Lanier, Elizabeth Wriothesley, Countess of Southampton but there are theories that his sonnets are actually about the countess’ husband Henry Wriothesley. Many people believe that Shakespare may have been into men and women. We’ll never know if he was a serial cheater for sure but if his steamy sonnets are any indication, he was definitely having multiple affairs.

4 Elizabeth Taylor

via Lisa's History Room

Elizabeth Taylor had eight marriages over the course of her life and numerous affairs, the most famous affairs involved Eddie Fisher who was married to Debbie Reynolds at the time. After Taylor's husband died suddenly in a plane crash, Fisher was there to be her shoulder to cry on and the two began an affair and he eventually left Reynolds for the actress. However, Fisher got a taste of his own medicine when Taylor met her future husband Richard Burton on the set of Cleopatra and the two began their famously torrid relationship and she divorced Fisher and married Burton a week later. She had many other affairs after her relationship with Burton and even remarried him years after they divorced only to divorce him again. As Cleopatra's actual relationship with Marc Antony was doomed from the start, so would the relationship of the actors who played the respective characters.

3 Catherine the Great

via WorldAtlas

Catherine the Great was known for her many affairs but she is probably known best of all for a rumor that was definitely untrue. The rumored affair is memorable because it involved a horse. Obviously, this rumor is completely untrue. Catherine had an arranged marriage to the heir of the Russian throne who was named Peter III but the two were not a match made in heaven. They were married for eight years and she bore him a son, Paul, who was probably not Peter's son as he looked very much like her lover Sergei Saltykov. She also had affairs with Stanislaus Poniatowski and Grigory Orlov while she was married and she bore them both children. Her husband was assented in 1762 and she never married again but she had many romantic entanglements. The rumor about the horse was believed to have been started in order to ridicule her for her many affairs. Say what you will about her but she definitely didn't deserve to be implicated in a rumor about her being in love with a horse.

2 Benjamin Franklin

via Salon

You may not know if from looking at a $100 bill but Benjamin Franklin was quite the babe magnet in his day. Though he was married to his wife Deborah for 44 years, he still fathered an illigitimate child on the sly who she eventually helped raise. He spent 18 years of their marraige away in London or Paris where he had many mistresses. In a famous letter to a friend, he explained how exactly to choose a mistress. He told his friend that he should always choose an older mistress rather than a younger one because you didn’t have to worry about them getting pregnant, they offered more stimulating conversation, and they would be much more likely to keep the affair to themselves. He basically gave his friend lessons on cheating. That’s right, this founding father was a grizzled, paunchy, randy old man. Just remember that the next time you see a $100 bill.

1 Donald Trump

via Gawker

Back before he was president, Donald Trump was still gross and had many affairs with various blond women. He had an infamous affair with Marla Maples while he was still married to Ivana Trump. He has since implied that there have been many more affairs than the one with Maples. A former bunny claimed to have been one of his mistresses over a decade ago while he was married to Melania. The National Enquirer paid her $150,000 for her account on her romantic entanglement with Trump but the story never ran. This is probably because the company has close ties to Trump and the idea of people being paid to keep quiet about affairs with Trump is not at all surprising. There is probably something there since they had to cover the story up. In an interview, Trump was asked about his affairs and he said that he never discussed it because "it was never a problem." Sure.

More in Entertainment